Index

Page numbers in bold indicate tables acetylcholinesterase 12 2-azidobiphenyls 477, 479 Acheson indole synthesis 506, 507 azirines 296–298 acid-catalyzed furan ring-opening 313–316 aeration oxygenation 549, 550 bacterial infections 4–5, 19, 76–77 Åkermark carbazole synthesis 600, 601 Baell indole synthesis 509, 510 alkyl phenylphosphonites 269 Baeyer–Jackson indole synthesis 363–364 alkyne cyclization 236, 240 Bailey–Liebeskind indole synthesis 213–216, 215 alkyne hydroamination 45–46, 55, 72 Bailey–Liebeskind–O’Shea indoline–indole synthesis 213–218 2-alkynylanilines 396–397, 400, 575–579 applications 213, 216 Allen and Weiss indole synthesis 190–191, 192, 193 Bailey–Liebeskind indole synthesis 213–216, 215 allene heteroannulation 623, 625 indoles produced 215 α-azidocinnamate esters 287–288, 293 mechanism 213, 214 α-diazoesters 450, 455 O’Shea indole synthesis 213, 216–217 Alzheimer’s disease 12 Barbier reaction 186–187 amine carbonyl ring closure 236, 239 Barluenga indole synthesis 500, 501, 528, 530, 592, 594 anilinopyridines 468, 470 Bartoli indole synthesis 121–130 anilinoquinolines 468, 470 applications 123–129 anion-sensing systems 22–24 functionalized indoles 127–128, 128–129 2-(arylamino)styrenes 673 indoles produced 121, 122 aryl azides 472, 478 Madelung indole synthesis 148, 153 1-arylcarbazoles 397, 401 mechanism 121 aryl-Heck indole-carbazole synthesis 597–599, 623, 629 modifications 121, 123, 129 arylhydrazides 67 naturally occurring indoles 123, 128 arylhydrazines 44–45, 50, 56, 57–60 pharmaceuticals containing indoles 126, 128 arylhydrazones 50, 57–58, 60–63, 66, 67 Barton-Ninomiya indole synthesis 548, 549 aryne intermediates Belley N-hydroxyindole synthesis 376, 377 Barluenga indole synthesis 528, 530 benzo[b]carbazoles 478, 480 Biehl indole synthesis 532 benzoquinone imines 206 Brown-Eastwood indole synthesis 528, 530 1,4-benzoquinones 191, 192, 193 Bunnett indole synthesis 528, 529 benzoquinones 188–205 Caubère indole synthesis 528, 529 Bergman carbazole-indole synthesis 438, 442 early indole syntheses 528, 529 Bergman cyclization 148 Greaney indole synthesis 532, 533 Bernier indole synthesis 194, 201 Greaney indoline-indole synthesis 535 β-dicarbonyl compounds 581–583 Guitán indole synthesis 528, 530 Biehl indole synthesis 532 He indole synthesis 533, 534 biindoles Iwao-Watanabe indole synthesis 528, 530 Cadogan–Sundberg indole synthesis 267, 269, 271 Kudzma indole-carbazole synthesis 528, 531, 532 copper-catalyzed indole ring synthesis 579 Larock indole synthesis 534, 535 Fischer indole synthesis 77, 102 Lin-Wang indole synthesis 532–533COPYRIGHTEDgold-catalyzed MATERIAL indole ring synthesis 640 Indoles via arynes in indole and carbazole synthesis 528–536 iridium-catalyzed indole ring synthesis 655 Sanz indole-carbazole synthesis 531, 532 Leimgruber–Batcho indole synthesis 347 Stoltz indoline-indole synthesis 535 ligands containing indoles 29 Studer indole synthesis 533, 534 materials containing indoles 21–23 Tokuyama indoline-carbazole synthesis 531, 532 Nenitzescu o,β-dinitrostyrene reductive cyclization 329 Wu-Sha indole synthesis 534–535 palladium-catalyzed indole ring synthesis 600, 607 Zhu indole synthesis 533, 534 biofouling 5 Zyryanov indoline-indole synthesis 535 biological activity of indoles 4–15 azacarbazoles 304–306 Alzheimer’s disease 12

Indole Ring Synthesis: From Natural Products to Drug Discovery, First Edition. Gordon W. Gribble. © 2016 John Wiley & Sons, Ltd. Published 2016 by John Wiley & Sons, Ltd.

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bacterial infections 4–5 CAN see cerium(IV) ammonium nitrate cancer 8, 10–12 cancer cannabimimetics 12–13 biological activity of indoles 8, 10–12 fungal infections 5 Fischer indole synthesis 73–75, 81–82, 97 inflammation 6–7, 8, 13 materials containing indoles 27–28 neurological disorders 7–8, 9, 12 pharmaceutical indole products 15–17 obesity and diabetes 7, 9 cannabimimetics 12–13 parasitic infections 5–6 carbazoles plant growth regulators 14–15 Åkermark carbazole synthesis 600, 601 tricyclic indoles 13–14 aryl-Heck indole-carbazole synthesis 597–599, 623, 629 viral infections 5–6, 7 Bergman carbazole-indole synthesis 438, 442 Bischler indole synthesis 249–259 Buchwald–Hartwig indole synthesis 619, 620 applications 251–256 Cadogan–Sundberg indole synthesis 266–267, 269, Black indole synthesis 250–251 271, 275 Buu-Hoi indole synthesis 250 cycloaddition syntheses from vinyl pyrroles 506 cryptolepine alkaloids 255, 255 Diels–Alder cycloaddition 437–451, 453–458 indoles produced 252–253 electrocyclization 489, 490 mechanism 249–250, 258 electrocyclization of pyrroles 515 modifications 250–251, 253–258 Fujii-Ohno indole synthesis 526 Moody indole synthesis 255–256 gold-catalyzed indole ring synthesis 640, 641 Reddy indole synthesis 257, 258 Graebe–Ullmann carbazole-carboline synthesis 424–434 Yu indole synthesis 256 Knochel indole synthesis 299 Bischler–Napieralski cyclization 318, 320 Knölker carbazole synthesis 391–395 1,2-bis(diphenylphosphino)ethane (DPPE) 271 Kudzma indole-carbazole synthesis 528, 531, 532 bismuth nitrate 41 Magnus carbazole-indole synthesis 438–439, 442 Black indole synthesis 250–251, 263 mercury-catalyzed indole ring synthesis 663, 664 Blechert indole synthesis 485, 487 miscellaneous indole ring-forming syntheses 673 Boger indole synthesis 458, 461, 464, 467 miscellaneous palladium-catalyzed syntheses 623–631 Borsche–Dreschel carbazole synthesis 66, 74–75 Mohanakrishnan carbazole synthesis 515 Boruah indole synthesis 194, 197 molybdenum-catalyzed indole ring synthesis 660, 662 Bredereck’s reagent 346–347 Moody carbazole synthesis 437–440 Brown-Eastwood indole synthesis 528, 530 naturally occurring indoles 4 Bucherer carbazole synthesis 66 nitrene cyclization 265 Buchwald indole synthesis 371, 372 Nozaki carbazole synthesis 619, 620 Buchwald–Hartwig indole synthesis 619–622 oxidative cyclization 397, 401 amination with C–H activation 619, 621 Petillo carbazole synthesis 519 applications 619–621 photolysis/photochemical synthesis 468–469, 472, 474, Nozaki carbazole synthesis 619, 620 477–480 Willis indole synthesis 619, 620 Plieninger–Moody carbazole synthesis 437, 438, 440–441 Buchward synthesis 98 indoles via arynes 528–536 Bunnett-Beugelmans indole synthesis 473, 475, 478–479 pyrrolo-2,3-quinodimethanes 519 Bunnett indole synthesis 528, 529 reviews of indole-ring synthesis 34 Burger indole synthesis 140, 143 rhodium-catalyzed indole ring synthesis 632, 633 Butin indole synthesis 313–316 Rossi indole-carbazole synthesis 474, 479 applications 313–314 ruthenium-catalyzed indole ring synthesis 646 indoles produced 315 Sanz indole-carbazole synthesis 531, 532 indolo[3,2-c]quinolines 314, 316 Schmittel indole synthesis 478, 479–480 mechanism 313 Smith carbazole synthesis 477, 479 butyrylcholinesterase 12 Sundberg indole synthesis 278–280, 282, 284–285 Buu-Hoi indole synthesis 250 Täuber carbazole synthesis 301–303 Tokuyama indoline-carbazole synthesis 531, 532 Cacchi indole synthesis 615–618 carbazolones 371, 373 applications 615–617 carbenoids 236, 239 Utimoto indole synthesis 615, 616 carbolines Cadogan–Sundberg indole synthesis 266–277 annulation of oxindoles 563–565 applications 266–267, 271 aryl-Heck indole-carbazole synthesis 597 biindoles 267, 269, 271 Cadogan–Sundberg indole synthesis 266 carbazoles 266–267, 269, 271, 275 Diels–Alder cycloaddition 453–454, 458, 461 Freeman indole synthesis 267, 269, 273 gold-catalyzed indole ring synthesis 640, 642 fused indoles 272 Graebe–Ullmann carbazole-carboline synthesis 424–434 indoles produced 268, 270 intramolecular anionic cycloaromatization 489, 490 mechanism 266, 267 naturally occurring indoles 4 modifications 267, 269–274 photolysis/photochemical synthesis 468, 470, 479 side reactions 271–272, 276 Quéguiner azacarbazole synthesis 304, 306

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carbolines (Cont’d) Diels–Alder cycloaddition 437–463, 506–510, 517–519 reviews of indole-ring synthesis 34 dipolar cycloaddition 483–486 ruthenium-catalyzed indole ring synthesis 646 Eguchi indole synthesis 506, 508 Sundberg indole synthesis 280, 284 electrocyclization 488–489, 491, 512–516 Castro–Stephens indole synthesis 575–577 Harman indole synthesis 509 catalytic dehydrogenation Hiremath-Schneller indole synthesis 506, 507 Barton-Ninomiya indole synthesis 548, 549 intramolecular anionic cycloaromatization 489, 490 chloranil 539, 541, 545 Jones indole synthesis 506, 507 Clive indoline dehydrogenation 539, 540 Muchowski indole synthesis 506, 508 Davies indole synthesis 520, 521 Murase indole synthesis 506–507, 508 2,3-dichloro-5,6-dicyano-1,4-benzoquinone 520–523, 539, Noland indole synthesis 506, 507 541–545 Pauson–Khand reaction 660, 661 Gribble indoline dehydrogenation 539, 540 photochemical synthesis of indoles and carbazoles 468–482 Inada indole synthesis 547, 549 platinum-catalyzed indole ring synthesis 649 indolines 539–552 Plieninger indole synthesis 464–467 manganese dioxide 544–546, 548 pyrroles 512–516 Matsumoto indole synthesis 520, 521 pyrrolo-2,3-quinodimethanes 517–519 Murakami indole synthesis 520, 522 Seitz indole synthesis 506, 508 Naito indoline dehydrogenation 539, 540 sigmatropic rearrangements 487–491 palladium and palladium-charcoal catalysts 520–521, 523, Tao indole synthesis 507, 508 539–541 vinyl pyrroles 506–511 pyrroles 520–524 Yamashita indole synthesis 507, 509 Remers indole synthesis 520, 521 Yoshida-Yanagisawa indole synthesis 509, 510 Saito indole synthesis 520, 522 cyclooxygenase (COX) inhibitors 6–7, 77–80 selenium-catalysts 548, 549–550 cyclopeptides 21 Somei N-hydroxyindole synthesis 546, 548–549 Tobinaga indole synthesis 520, 522 Dalla Croce indole synthesis 553, 554 catalytic hydrogenation 325, 330, 349–352 Danheiser indole synthesis 488–489, 490, 514, 515 cation-sensing systems 24 Danishefsky indole synthesis 488, 489 Caubère indole synthesis 528, 529 Davies indole synthesis 520, 521 CDK see cyclin-dependent kinases DCA see dipolar cycloaddition cerium(IV) ammonium nitrate (CAN) 196 DDQ see 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chapman indoline-indole synthesis 471, 472 Demopoulos indole synthesis 497, 498 chemosensors 22–24 diabetes 7, 80–81, 90 Cheng indole synthesis 487, 488 dialkyl phosphites 269, 273 chloranil 539, 541, 545 2,2’-diaminobiphenyls 301–303 Cho carbazole synthesis 302–303 diazonium salts cholesterol 7, 18 Baeyer–Jackson indole synthesis 363 Chou indole synthesis 517, 518 Fischer indole synthesis 50, 56, 60–62, 66, 98 chromium-catalyzed indole ring synthesis 663, 664 miscellaneous indole ring-forming syntheses 672 Claisen-type rearrangements 287 Murphy indole synthesis 412–413 Clark indole synthesis 147, 151 indoles via arynes 528 Clive indoline dehydrogenation 539, 540 DIBAL see diisobutylaluminum hydride cobalt-catalyzed indole ring synthesis 660, 661 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) 520–523, conjugate addition reactions 232, 236–237 539, 541–545 copper-catalyzed indole synthesis 575–587 dictyodendrins 280, 282 2-alkynylanilines 575–579 Diels–Alder cycloaddition 437–463 Castro–Stephens indole synthesis 575–577 applications 437–439 2-ethynylanilines 577–579 asymmetric indole syntheses 446–447 2-haloanilines and β-dicarbonyl compounds 581–583 Bergman carbazole-indole synthesis 438, 442 intramolecular amination route 579–581 Boger indole synthesis 458, 461 miscellaneous indole ring-forming syntheses 583–585 carbazoles 437–451, 453–458 N-2-haloaryl enaminones 581, 582 carbolines 453–454, 458, 461 Saegusa indole synthesis 221 2,4-dihydropyrrolo[3,4-b]indoles 446–448, 451 Watanabe indole synthesis 383, 385 Fischer indole synthesis 98 Correia indole synthesis 592–593, 594 Franck indole synthesis 455, 460 Couture indole synthesis 174–175 fused indoles 437 COX see cyclooxygenase Ghosez indole synthesis 453, 457 cryptolepine alkaloids 255, 255 Gribble indole syntheses 448–452 cyclin-dependent kinases (CDK) 82 hetero-Diels–Alder cycloaddition 441, 446 cycloaddition and electrocyclization 4H-furo[3,4-b]indoles 448–451, 452, 454–456 Acheson indole synthesis 506, 507 Hoornaert indole synthesis 458, 461 Baell indole synthesis 509, 510 indole-2,3-quinodimethanes 437–449

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intramolecular Diels–Alder cycloaddition 449–450, Townsend indole synthesis 512, 513 453–455, 457 van Leusen indole synthesis 512, 513 Kanematsu indole synthesis 454, 458 Vedejs indole synthesis 512, 513 Kreher indole synthesis 447, 450 Weber indole synthesis 512, 513 Magnus carbazole-indole synthesis 438–439, 442 electrophilic cyclization mechanism 437–439, 441, 443–445 Barluenga indole synthesis 500, 501 Molina indole synthesis 453–454, 457 Bischler indole synthesis 249–259 Moody carbazole synthesis 437–440 Butin indole synthesis 313–316 Padwa indole syntheses 451, 455, 456, 458, 460 Cadogan–Sundberg indole synthesis 266–277 Plieninger–Moody carbazole synthesis 437, 438, Demopoulos indole synthesis 497, 498 440–441 Feldman indole synthesis 311–312 pyrrolo-2,3-quinodimethanes 517–519 France indole synthesis 499, 500 Saá indole synthesis 454–455, 459 Gelb indole synthesis 497, 498 Shafiee indole synthesis 451, 453, 457 Hemetsburger indole synthesis 287–295 Sha indole synthesis 447, 449 Hewson indole synthesis 309 Snyder indole synthesis 447–448, 450 Ila-Junjappa indole synthesis 499, 500 Srinivasan indole synthesis 447, 450 Ishibashi indole synthesis 496–497, 498 vinyl pyrroles 506–510 Iwao indole synthesis 307–308 Wasserman indole synthesis 455, 459 Kashima indole synthesis 500, 501 Welch indole synthesis 446–447, 449 Katritzky indole syntheses 497, 499 Wipf indole synthesis 458, 460 Kikugawa indole synthesis 265 Witulski indole synthesis 454, 459 Klemm–Horaguchi indole synthesis 264–265 difluorostyrenes 228–229 Knochel indole synthesis 299–300 2,4-dihydropyrrolo[3,4-b]indoles 446–448, 451 Kozikowski indole synthesis 496, 497 5,6-dihydroxyindoles 396, 397 Latos-Grażyński indole synthesis 497, 498 dihydroxyphenylalanine (DOPA) 396 Magnus indole synthesis 310 diisobutylaluminum hydride (DIBAL) miscellaneous indole ring-forming syntheses 317–321, 673 Diels–Alder cycloaddition 447–448 Murakami indole synthesis 496, 497 Mąkosza indole synthesis 358 Natsume and Muratake indole synthesis 495–496 oxindole reduction 558, 560 nitrene cyclization 264–265, 287–295, 299–300 reductive cyclization 369 Nordlander indole synthesis 260–263 N,N-dimethylformamide dimethyl acetal (DMF-DMA) pyrroles 495–502 317, 319 Quéguiner azacarbazole synthesis 304–306 dimethyl(methylthio)sulfonium trifluoromethanesulfonate Sugasawa indole synthesis 244–245 (DMTST) 317, 319 Sundberg indole synthesis 278–286 diphenylamines 468, 469 Taber indole synthesis 296–298 dipolar cycloaddition (DCA) 483–486 Täuber carbazole synthesis 301–303 1,3-dipolar cycloaddition 483–486 Török indole synthesis 500, 501 [3+2] dipolar cycloaddition 483–487 Trost indole synthesis 496, 498 [1+4] dipolar cycloaddition 483, 485, 487 eletriptan 72 DMTST see dimethyl(methylthio)sulfonium ellipticine ­trifluoromethanesulfonate Diels–Alder cycloaddition 438, 446–447, 449, 451, 453 DOPA see dihydroxyphenylalanine Graebe–Ullmann carbazole-carboline synthesis

dopamine D2 receptor antagonists 72 426–427, 432 DPPE see 1,2-bis(diphenylphosphino)ethane enamino ketones 471, 478 Driver indole synthesis 633, 636 enehydrazines 44, 46, 50, 56, 59, 82, 106–107 drug products see pharmaceutical indole products Engler indole synthesis 206–209 drug resistance 4–5, 7, 76–77 Engler–Kita indole synthesis 206–212 applications 212 Eguchi indole synthesis 506, 508 Engler indole synthesis 206–209 Eimeria spp. 77 Kita indole synthesis 206, 210–211 electrocyclization 488–489, 491 mechanism 206, 209 Danheiser indole synthesis 514, 515 modifications 211 Funk indole synthesis 512–514 epoxide ring opening reactions 232, 235, 236, 238 Fürstner indole synthesis 514, 515 Escherichia coli 77 Giomi indole synthesis 515 estrogen-receptor ligands 77 Hibino indole synthesis 512, 513 2-ethynylanilines 577–579 Kagan indole synthesis 512, 513 Langer indole synthesis 512, 513 Fagnou indole synthesis 632, 634 Mohanakrishnan carbazole synthesis 515 Feldman indole synthesis 311–312 Oda-Machida indole synthesis 512, 513 dipolar cycloaddition 483, 486 pyrroles 512–516 mechanism 311, 312 Shannon indole synthesis 512, 513 side reactions 311, 312

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Fischer carbene complexes 663, 664 Wittig–Madelung indole synthesis 156 Fischer indole synthesis 41–115 see also carbolines applications 68–107 Fuwa-Sasaki indole synthesis 592, 594 hydrazones 63, 67, 68 FVP see flash vacuum pyrolysis materials containing indoles 97–101 mechanism 41 Gallou indole synthesis 371, 372 metal-catalyzed methods 44–59 Gassman indole synthesis 116–120 methods 41–68 applications 119–120 naturally occurring indoles 82–97, 91–93 indoles prepared by 117–118 novel applications 98–107 mechanism 116 other general methods 57–66 modifications 116, 119 pharmaceutical indole products 68–82, 83–86 Gelb indole synthesis 497, 498 Rawal indole synthesis 362 Ghosez indole synthesis 453, 457 solid-phase Fischer indolization method 56–57, 60 Giomi indole synthesis 515 traditional methods 41–44, 47–49, 50, 51–52 Glorius indole synthesis 593, 595, 632, 635 variations 66, 68 glutathione 80 zinc-catalyzed indole ring synthesis 651 glycogen synthase kinase-3 (GSK-3) 12 flash vacuum pyrolysis (FVP) 415 gold-catalyzed indole ring synthesis 640–644 Graebe–Ullmann carbazole-carboline synthesis 425, carbazoles 640, 641 426–427, 430 carbolines 640, 642 miscellaneous indole ring-forming syntheses fused indoles 640, 642 671–672 G-quadruplex DNA 27–28 fluorescence devices 24–26 Graebe–Ullmann carbazole-carboline synthesis 424–434 fluoride-sensing systems 22 applications 426–433 Foucaud indole synthesis 483, 485, 487 ellipticine 426–427, 432 France indole synthesis 499, 500 flash vacuum pyrolysis 425, 426–427, 430 Franck indole synthesis 455, 460 fused carbolines 432 Freeman indole synthesis 267, 269, 273 mechanism 424–426, 430 Friedel–Crafts reaction 317, 319 microwave-assisted synthesis 426, 431 Friedlander indole synthesis 568, 569 modifications 424–426 Fujii-Ohno indole synthesis 526 photolysis/photochemical syntheses 424–425, 428 Fukuyama indole synthesis 405–408 thermolysis 424–426 applications 405–408 1,2,3-triazoles 425, 430 electrophilic cyclization 307–308 Grandberg synthesis 66, 70–72, 75, 80, 82, 102 imidoyltellurides 405, 408 Greaney indole synthesis 532, 533 indoles produced 406, 407 Greaney indoline-indole synthesis 535 mechanism 405, 406 Gribble indole synthesis 448–452, 518–519 modifications 405 Gribble indoline dehydrogenation 539, 540 reductive cyclization 345, 346 Grignard reagents thioanilides 405, 407 Bartoli indole synthesis 121, 128–129 functionalized elimination Fischer indole synthesis 50, 56 Dalla Croce indole synthesis 553, 554 Knochel indole synthesis 299–300 indolines 553–557 miscellaneous indole ring-forming syntheses 666, 667 Kikugawa indole synthesis 553, 554 Grubbs catalyst 46, 646–647 miscellaneous indoline to indole conversions 553–554, GSK-3 see glycogen synthase kinase-3 555–556 Guitán indole synthesis 528, 530 N-sulfinate elimination 553, 555 Overton indole synthesis 553, 554 2-haloanilines 581–583 Plieninger indole synthesis 553, 554 halocyclization 673, 674 Thesing indole synthesis 553, 554 2-haloindole-3-carbaldehydes 561–563 fungal infections 5–6 2-haloindoles 561–563 Funk indole synthesis 488, 489, 512–514 Hantzsch thiazole synthesis 43 furan ring-opening 313–316 Harman indole synthesis 509 Fürstner indole synthesis 514, 515 HCV see hepatitis C virus fused indoles HDAC see histone deacetylases annulation of oxindoles 563–565 Hegedus indole synthesis 588–591 Diels–Alder cycloaddition 437 applications 588, 590 gold-catalyzed indole ring synthesis 640, 642 mechanism 588, 589 Molina, Alajarán, and Vidal indole synthesis 416 He indole synthesis 533, 534 Nenitzescu 5-hydroxyindole synthesis 194 Hemetsburger indole synthesis 287–295 nitrene cyclization 264 applications 287–288, 290–293 Sundberg indole synthesis 280, 283, 284 indoles produced 287, 289–290, 292–293 Wang indole synthesis 416 mechanism 287

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modifications 293–294 indoline-2-thiones 565 naturally occurring indoles 287–288, 290, 293 indolocarbazoles pharmaceuticals containing indoles 287, 291 Fischer indole synthesis 96–98 hepatitis C virus (HCV) 6, 75 naturally occurring indoles 4 hetero-Diels–Alder cycloaddition 441, 446 pharmaceutical indole products 16–17 Hewson indole synthesis 309 reviews of indole-ring synthesis 34 4H-furo[3,4-b]indoles 448–451, 452, 454–456 indoloquinazolines 483, 486 Hibino indole synthesis 512, 513 indolo[3,2-c]quinolines 314, 316 Hidai indole synthesis 503, 504 indoloquinolines 478, 480 Hiremath-Schneller indole synthesis 506, 507 3-indolyl triflates 568, 570 histone deacetylases (HDAC) 16 indoxyls 558, 567–569 HIV/AIDS 5–7, 19, 76 applications of 3-indolyl triflates 568, 570 Hofmann rearrangement 363 C-2 reactions of N-protected indoxyls 568, 569 Hoornaert indole synthesis 458, 461 Friedlander indole synthesis 568, 569 Horner–Witting reagents 174–175 ketone reactions of N-protected indoxyls 567–568 Hossain indole synthesis 366 inflammation 5-HT see serotonin biological activity of indoles 6–7, 8, 13 Huang indole synthesis 632, 635 Fischer indole synthesis 77–80, 93 Hughes indole synthesis 158, 163 pharmaceutical indole products 21 human papillomaviruses (HPV) 75–76 intramolecular amination Hwu indole synthesis 139, 142 Buchwald–Hartwig indole synthesis 619, 621 hydroamination copper-catalyzed indole synthesis 579–581 Fischer indole synthesis 45–46, 55, 72 Hegedus indole synthesis 588 silver-catalyzed indole ring synthesis 651, 653 ruthenium-catalyzed indole ring synthesis 646 zinc-catalyzed indole ring synthesis 651, 654 intramolecular anionic cycloaromatization 489, 490 hydroformylation 45 intramolecular Barbier reaction 186–187 hydrous zirconia-supported niobium oxide 41 intramolecular Diels–Alder cycloaddition 449–450, hydroxyindoles 453–455, 457 5,6-dihydroxyindoles 396, 397 iodocyclization 673, 674 Leimgruber–Batcho indole synthesis 343–344 ionic liquids 41 Nenitzescu 5-hydroxyindole synthesis 188–205 IQD see indole-2,3-quinodimethanes Somei 1-hydroxyindole synthesis 343–344 iridium-catalyzed indole ring synthesis 655, 658 see also N-hydroxyindoles Watanabe indole synthesis 383, 387 iron-catalyzed indole ring synthesis 655, 656–657 Ichikawa indole synthesis 228–229 iron/acetic acid 325–326, 329–330, 352 Ila-Junjappa indole synthesis 499, 500 iron(III) chloride-mediated cyclization 396, 399 Imamoto indole synthesis 156–157, 160 isatins 558, 565–567 Imaniski indole synthesis 156, 159 Ishibashi indole synthesis 496–497, 498 imidoyl substrates 409 Iwao indole synthesis 307–308 imidoyltellurides 405, 408 Fukuyama indole synthesis 307–308 Inada indole synthesis 547, 549 mechanism 307, 308 indium-catalyzed indole ring synthesis 655, 658 Iwao-Watanabe indole synthesis 528, 530 indole-containing natural products see naturally Iwasawa indole synthesis 483, 486 occurring indoles indole–oxazoline ligands 31–32 Japp–Klingemann synthesis 66, 72–73, 76, 81–82, 98–102, indole–phosphine ligands 29–31 103–104 indole–phosphine–oxazoline ligands 30 Jones indole synthesis 506, 507 indole-2,3-quinodimethanes (IQD) 437–449 Jones–Schmid indole synthesis 165–173 indolines indoles produced 167–168 Bailey–Liebeskind–O’Shea indoline–indole synthesis mechanism 165, 166 213–218 modifications 165, 168–172 catalytic dehydrogenation 539–552 Mohanakrishnan indole synthesis 171, 172 from oxindoles, isatins, and indoxyls 558–572 Nenitzescu indole synthesis 165, 170, 171 functionalized elimination 553–557 N,O-diacetylindoxyls 171, 171 indoxyls 558, 567–569 Opatz indole synthesis 165, 170 iridium-catalyzed indole ring synthesis 655 Stevens indole synthesis 165, 169 isatins 558, 565–567 Stevens–Opatz indole synthesis 165, 169 oxindoles 558–565 Julia indole synthesis 137–138 photolysis/photochemical synthesis 471, 472, 477–479 pyrroles via arynes 531, 532, 535 Kagan indole synthesis 512, 513 radical cyclization 414–415 Kanematsu indole synthesis 454, 458 tin-mediated cyclization 410 Kashima indole synthesis 500, 501 Wright indoline synthesis 219–220 Katritzky indole syntheses 497, 499

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Katukojvala indole synthesis 526 indoles produced 149–150, 154 Kerr indole synthesis 464, 466, 483, 485 mechanism 147 Kihara indole synthesis 186–187 modifications 147–148, 151, 153 Kikugawa indole synthesis 265, 553, 554 Wacker solid-phase synthesis 148, 153 kinase inhibitors 81–82 see also reverse-Madelung indole synthesis; Wittig–Madelung Kita indole synthesis 206, 210–211, 396, 397 indole synthesis Klemm–Horaguchi indole synthesis 264–265 Magnus carbazole-indole synthesis 438–439, 442 Knochel indole synthesis 299–300 Magnus indole synthesis 310 Knoevenagel reaction 446 Majumdar synthesis 131, 135 Knölker carbazole synthesis 391–395 Makisumi and Takada synthesis 131, 133 applications 392–393 Mąkosza indole synthesis 354–360 crossover experiment 393, 394 applications 354–355, 357–359 mechanism 391–394 indoles produced 356–357, 359 Kočevar indole synthesis 488, 490 Macor indole synthesis 354, 357–358 Koser reagent 397 mechanism 354, 355 Kozikowski indole synthesis 483, 484, 496, 497 modifications 354, 357–359 Krapcho decarbomethoxylation and oxidation 219–220 Mancini indole synthesis 525 Kraus indole synthesis 157, 161–162, 464, 465 manganese dioxide 544–546, 548 Kreher indole synthesis 447, 450 manganese(III) acetate 414 Kruse indole synthesis 342–343 marine biofouling 5 Kuckländer indole synthesis 193, 195 Martin indole synthesis 139, 141 Kudzma indole-carbazole synthesis 528, 531, 532 materials containing indoles 21–28 Kulkarni indole synthesis 366 chemosensors and receptors 22–24 Fischer indole synthesis 97–101 LAH see lithium aluminum hydride fluorescence and luminescence devices 24–26 Langer indole synthesis 512, 513 G-quadruplex DNA 27–28 Larock indole synthesis 611–614 organic electronic materials 26–27 applications 611–613 Matsumoto indole synthesis 520, 521 aryne intermediates 534, 535 MCH see melanin-concentrating hormone mechanism 611 Meerwein arylation reaction 363, 366 Latos-Grażyński indole synthesis 497, 498 Meinwald rearrangement 59 Lautens indole synthesis 503, 505, 632, 635 melanin-concentrating hormone (MCH) 81 Leditschke carbazole synthesis 301–302 Meldrum’s acid 139 Leimgruber–Batcho indole synthesis 338–348 mercury-catalyzed indole ring synthesis 663, 664 applications 338–341 Meslin indole synthesis 489, 490 Fukuyama indole synthesis 345, 346 metal–halogen exchange, indole ring-formation 241 indoles produced 340, 346 methicillin-resistant Staphylococcus aureus (MRSA) 76 Kruse indole synthesis 342–343 Michael addition 232, 236–237 mechanism 338, 339 microwave-promoted indole ring synthesis miscellaneous indole ring-forming syntheses 367, 370 Fischer indole synthesis 41–43, 58 modifications 342–347 Graebe–Ullmann carbazole-carboline synthesis 426, 431 piperidine 342 reviews of indole-ring synthesis 33 pyrrolidine 338–341 migraine 18, 69–71 Somei 1-hydroxyindole synthesis 343–344 Minutolo N-hydroxyindole synthesis 336, 337 Leishmania donovani 86, 89 Miura-Satoh indole synthesis 503, 505 leukotriene receptor antagonists 13 Mohanakrishnan carbazole synthesis 515 ligands containing indoles 28–32 Mohanakrishnan indole synthesis 171, 172 indole–oxazoline ligands 31–32 Molina, Alajarán, and Vidal indole synthesis 416, 421 indole–phosphine ligands 29–31 Molina indole synthesis 453–454, 457 indole–phosphine–oxazoline ligands 30 molybdenum-catalyzed indole ring synthesis 660, 662 novel indole ligands 31–32 Moody carbazole synthesis 437–440 Li indole synthesis 396, 399 Moody indole synthesis 255–256, 518, 634, 638 Lim and Patil indole synthesis 396, 397 Mori–Ban–Heck indole synthesis 592–596 Lin-Wang indole synthesis 532–533 applications 592–593, 594 lithium aluminum hydride (LAH) 558 Barluenga indole synthesis 592, 594 luminescence devices 24–26 Correia indole synthesis 592–593, 594 Fuwa-Sasaki indole synthesis 592, 594 Macor indole synthesis 354, 357–358 Glorius indole synthesis 593, 595 Madelung indole synthesis 147–155 mechanism 592, 593 applications 147, 152 modifications 593–595 Bartoli modification 148, 153 MRSA see-ethicillin-resistant Staphylococcus aureus Clark modification 147, 151 Muchowski indole synthesis 506, 508 electron-withdrawing activation 147–148, 154 Mukaiyama–Michael reactions 317, 320

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Murakami indole synthesis 496, 497, 503, 504, 520, 522 Nicolaou N-hydroxyindole synthesis 335–337, 376 Murase indole synthesis 506–507, 508 Nicolaou tryptamine synthesis 176, 179 Muratake-Natsume indole synthesis 503, 504 niobium-catalyzed indole ring synthesis 666, 667 Murphy indole synthesis 412–413 nitrene cyclization 264–265 Mycobacterium tuberculosis 77 Hemetsburger indole synthesis 287–295 Myers indole synthesis 376, 378 Kikugawa indole synthesis 265 Klemm–Horaguchi indole synthesis 264–265 Naito indoline dehydrogenation 539, 540 Knochel indole synthesis 299–300 Nakamura indole synthesis 634, 638 nitro ketones 370–371 Natsume and Muratake indole synthesis 495–496 N-methyl-D-aspartate (NMDA) receptor 12–13, 72–73 naturally occurring indoles 1–4 N,O-diacetylindoxyls 171, 171 Bartoli indole synthesis 123, 128 Noland indole synthesis 506, 507 electrophilic cyclization of pyrroles 496 nonsteroidal androgen-receptor antagonists 77 Fischer indole synthesis 82–97, 91–93 Nordlander indole synthesis 260–263 Graebe–Ullmann carbazole-carboline synthesis 426–433 Black indole synthesis 263 Hegedus indole synthesis 588 indoles produced 262 Hemetsburger indole synthesis 287–288, 290, 293 mechanism 260, 261 Larock indole synthesis 611–612 modifications 260–261 Leimgruber–Batcho indole synthesis 339–341 Nozaki carbazole synthesis 619, 620 marine indoles 1–2, 82, 86, 287–288 N-sulfinate elimination 553, 555 Nenitzescu o,β-dinitrostyrene reductive cyclization 325–326 nucleophilic cyclization Plieninger indole synthesis 464, 467 alkyne cyclization route for indole ring-formation 236, 240 Rawal indole synthesis 361–362 amine carbonyl ring closure route for indole ring-forma- terrestrial indoles 1, 3 tion 236, 239 Watanabe indole synthesis 389 Bailey–Liebeskind–O’Shea indoline–indole synthesis Nenitzescu 5-hydroxyindole synthesis 188–205 213–218 Allen and Weiss indole synthesis 190–191, 192, 193 carbenoid route for indole ring-formation 236, 239 applications 188, 190, 202–204 Couture indole synthesis 174–175 1,4-benzoquinones 191, 192, 193 Engler–Kita indole synthesis 206–212 Bernier indole synthesis 194, 201 epoxide ring opening route for indole ring-formation 232, Boruah indole synthesis 194, 197 235, 236, 238 drug targets and pharmaceuticals 194, 198–200 Ichikawa indole synthesis 228–229 indoles produced 198–200 Jones–Schmid indole synthesis 165–173 Kuckländer indole synthesis 193, 195 Kihara indole synthesis 186–187 mechanism 188, 189, 191, 193, 194 Madelung indole synthesis 147–155 modifications 188–191, 193–197, 201, 204 metal–halogen exchange route for indole ring-formation 241 Patrick and Saunders indole synthesis 193–194, 196 Michael and conjugate addition route for indole ring-forma- Steck indole synthesis 193–194, 198, 199 tion 232, 236–237 Troschütz indole synthesis 194, 201 miscellaneous indole ring-forming syntheses 230–243 Velezheva indole synthesis 194, 197 Nenitzescu 5-hydroxyindole synthesis 188–205

Nenitzescu indole synthesis 165, 170, 171 nucleophilic substitution (SNAr) route for indole Nenitzescu o,β-dinitrostyrene reductive cyclization ring-formation 230, 231–232, 236 325–331 Saegusa indole synthesis 221–227 applications 325, 328–330 Selvakumar indole synthesis 230, 232, 233 catalytic hydrogenation 325, 330 Smith indole synthesis 181–185 indoles produced 327, 329 Sugasawa indole synthesis 244–245 iron/acetic acid 325–326, 329–330 sulfonium ylide route for indole ring-formation 232, 234 mechanism 325, 326 Wender indole synthesis 176–180 modifications 325–326, 328–330 Wittig–Madelung indole synthesis 156–164 naturally occurring indoles 325–326 Wright indoline synthesis 219–220 neurological disorders 7–8, 9, 12, 18–19 N-2-haloaryl enaminones 581, 582 o-alkenylthioanilides 414 N-hydroxyindoles obesity 7, 9, 80–81, 90 Belley N-hydroxyindole synthesis 376, 377 Oda-Machida indole synthesis 512, 513 catalytic dehydrogenation of indolines 546, 548–549 OFET see organic field-effect transistors Foucaud indole synthesis 483, 485, 487 Oikawa, Yonemitsu indole synthesis 139, 140 Minutolo N-hydroxyindole synthesis 336, 337 Olah carbazole synthesis 302–303 Nicolaou N-hydroxyindole synthesis 376 OLED see organic light-emitting diodes reductive cyclization 375–377 o-nitrocinnamide 363 Reissert indole synthesis 335–337 o-nitrophenylacetaldehyde acetals 366–367 Somei N-hydroxyindole synthesis 546, 548–549 o-nitrophenylacetaldehyde dialkyl acetals 367–370, 368–369 nickel-catalyzed indole ring synthesis 660, 661 o-nitrophenylacetaldehydes 363, 365 radical cyclization 414 o-nitrophenyl ketones 370–371

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o-nitrophenylpyruvic acid 332 allene heteroannulation 623, 625 o-nitrotoluenes 383, 389 aryl-Heck indole-carbazole synthesis 597–599, Opatz indole synthesis 165, 170 623, 629 opium alkaloid analogues 93, 95–96 Buchwald–Hartwig indole synthesis 619–622 organic field-effect transistors (OFET) 26 Cacchi indole synthesis 615–618 organic light-emitting diodes (OLED) 26 electrophilic cyclization 317 organoaluminum reagents 46 Hegedus indole synthesis 588–591 organolithium reagents Hidai indole synthesis 503, 504 Bailey–Liebeskind–O’Shea indoline–indole synthesis indole syntheses via C–H activation 624–625, 626 213–218 Larock indole synthesis 611–614 Feldman indole synthesis 311–312 Lautens indole synthesis 503, 505 Fischer indole synthesis 46 Leimgruber–Batcho indole synthesis 338, 347 Hewson indole synthesis 309 Martin indole synthesis 139 indole ring-formation 232, 235, 236, 239 miscellaneous indole and carbazole syntheses 623–631 Iwao indole synthesis 307–308 Miura-Satoh indole synthesis 503, 505 Kihara indole synthesis 186–187 Mori–Ban–Heck indole synthesis 592–596 Magnus indole synthesis 310 Murakami indole synthesis 503, 504 Quéguiner azacarbazole synthesis 304–306 Muratake-Natsume indole synthesis 503, 504 Saegusa indole synthesis 221–227 Nenitzescu o,β-dinitrostyrene reductive cyclization 328 Smith indole synthesis 181–185 Pschorr–Hoppe indole synthesis 349 Wender indole synthesis 176–180 pyrroles 503–505 ortho-alkylamides 147 reductive cyclization 369 ortho-alkylnitrobenzenes 266 Suzuki palladium-catalyzed cross-coupling synthesis 271 ortho-azidobiphenyls 279–280, 284 Watanabe–Cenini–Söderberg indole synthesis 604–606 ortho-azidostyrenes 278 Yamanaka–Sakamoto–Sonogashira indole synthesis ortho,β-dinitrostyrenes 325–331 607–610 ortho-tolylisocyanides 221–222 parasitic infections 5–6, 76, 77, 86, 89 ortho-trimethylsilylmethyl anilides 148 PARP see poly(ADP-ribose) polymerase O’Shea indole synthesis 213, 216–217 Parsons indole synthesis 139, 142 Overton indole synthesis 553, 554 Patrick and Saunders indole synthesis 193–194, 196 oxidative cyclization Pauson–Khand reaction 660, 661 2-alkynylanilines 396–397, 400 p-benzoquinone dehydrogenation 523 1-arylcarbazoles 397, 401 Penoni indole synthesis 487–488, 489 iron(III) chloride-mediated cyclization 396, 399 peroxide-mediated radical cyclization 415 Kita indole synthesis 396, 397 Petillo carbazole synthesis 519 Knölker carbazole synthesis 391–395 pharmaceutical indole products 15–21 Li indole synthesis 396, 399 bacterial infections 19 Lim and Patil indole synthesis 396, 397 Bartoli indole synthesis 126, 128 miscellaneous indole ring-forming syntheses 396–402 cancer 15–17 PIFA/PIDA route 396–398, 400–401 cholesterol 18 Watanabe indole synthesis 383–390 Fischer indole synthesis 68–82, 83–86 Zhou indole synthesis 396, 398, 399 Hemetsburger indole synthesis 287, 291 oxindoles 558–565 inflammation 21 annulation to fused indoles 563–565 migraine 18 applications of 2-haloindoles/2-haloindole-3-carbaldehydes Nenitzescu 5-hydroxyindole synthesis 194, 198–200 561–563 serotonin receptors 18–19, 21 applications of 2-oxygenated indoles 563, 564 viral infections 19–20 diisobutylaluminum hydride 558, 560 phenylhydrazines 41–46, 57, 62, 66, 74–77, 80–82, 93, 98 indoline-2-thiones 565 phenylhydrazones 41–44, 46, 66, 98 Kubo indole synthesis 561 phenyliodine (III) bis(trifluoroacetate) (PIFA) 396–398 lithium aluminum hydride 558, 559 phenyliodine (III) diacetate (PIDA) 296, 298, 396–398, phosphorus oxychloride 560–562 400–401 Powers indole synthesis 560, 561 phosphonium ylides 414–416 Schulte indole synthesis 560–561 phosphorus oxychloride 560–562 sodium borohydride 558, 559 photolysis/photochemical synthesis oxiranes 236, 238 Bunnett-Beugelmans indole synthesis 473, 475, 478–479 5-oxygenated indoles 396, 397 carbazoles 468–469, 472, 474, 477–480 carbolines 468, 470, 479 Paal-Knorr pyrrole synthesis 499–500 Chapman indoline-indole synthesis 471, 472 Padwa indole syntheses 451, 455, 456, 458, 460 Graebe–Ullmann carbazole-carboline synthesis 424–425, 428 palladium-catalyzed dehydrogenation 520–521, 523, 539–541 indolines 471, 472, 477–479 palladium-catalyzed indole ring synthesis mechanism 468, 470 Åkermark carbazole synthesis 600, 601 miscellaneous indole and carbazole syntheses 468–482

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photocyclization of enamino ketones and nitriles 471, 478 Quéguiner azacarbazole synthesis 304–306 photocyclization of pyrrole analogues of stilbene applications 304, 306 473, 478 carbolines 304, 306 photocyclization of triphenylamine 468, 470 mechanism 304, 305 photocyclodehydrogenation of anilinopyridines and Quéguiner indole synthesis 525 ­anilinoquinolines 468, 470 photocyclodehydrogenation of diphenylamines 468, 469 radical cyclization photolysis of aryl azides 472, 478 Fukuyama indole synthesis 405–408 quinones, quinone imides, and (iso)quinoline N-oxides 476 Graebe–Ullmann carbazole-carboline synthesis 424–434 Rossi indole-carbazole synthesis 474, 479 miscellaneous indole ring-forming syntheses 414–423 Schmittel indole synthesis 478, 479–480 miscellaneous tin-mediated indole syntheses 409–411 Schultz indoline-indole synthesis 471, 477 Molina, Alajarán, and Vidal indole synthesis 416, 421 Smith carbazole synthesis 477, 479 Murphy indole synthesis 412–413 Yamada indoline-indole synthesis 471, 477 Wang indole synthesis 416, 422 Pictet–Spengler cyclization 62 Raney nickel PIDA see phenyliodine (III) diacetate catalytic dehydrogenation of indolines 547, 549 PIFA see phenyliodine (III) bis(trifluoroacetate) electrophilic cyclization of pyrroles 499, 500 Piloty–Robinson indole synthesis 66 Leimgruber–Batcho indole synthesis 338, 341 Pindur indole synthesis 156, 159 miscellaneous indole ring-forming syntheses 672 Pinna indole synthesis 139, 141 Watanabe indole synthesis 383 piperidine 342 Raucher indole synthesis 363, 365, 366 PKC see protein kinase C Rawal indole synthesis 361–362 Plancher rearrangement 102 Reddy indole synthesis 257, 258 plant growth regulators 14–15 reductive cyclization platinum-catalyzed indole ring synthesis 648–650 Baeyer–Jackson indole synthesis 363–364 Plieninger indole synthesis 464–467 Belley N-hydroxyindole synthesis 376, 377 Boger indole synthesis 464, 467 Buchwald indole synthesis 371, 372 functional elimination of indolines to indoles 553, 554 early indole syntheses 363–364 Kerr indole synthesis 464, 466 Gallou indole synthesis 371, 372 Kraus indole synthesis 464, 465 Hossain indole synthesis 366 mechanism 464, 465 Kulkarni indole synthesis 366 modifications 464–467 Leimgruber–Batcho indole synthesis 338–348, 367, 370 Plieninger–Moody carbazole synthesis 437, 438, 440–441 Mąkosza indole synthesis 354–360 poly(ADP-ribose) polymerase (PARP) 16 miscellaneous indole ring-forming syntheses 363–380 polyphosphoric acid (PPA) catalysis 77 Myers indole synthesis 376, 378 Powers indole synthesis 560, 561 Nenitzescu o,β-dinitrostyrene reductive cyclization PPA see polyphosphoric acid 325–331 prostaglandins 77–80 N-hydroxyindoles 375–377 protein kinase C (PKC) enzymes 16–17 Nicolaou N-hydroxyindole synthesis 376 Pschorr–Hoppe indole synthesis 349–353 nitro ketones 370–371 applications 349–351 o-nitrophenylacetaldehyde acetals 366–367 indoles produced 351–352 o-nitrophenylacetaldehyde dialkyl acetals 367–370, mechanism 349 368–369 modifications 349–350 o-nitrophenylacetaldehydes 363, 365 Snyder indole synthesis 349, 350 Pschorr–Hoppe indole synthesis 349–353 Stephen and Walker indole synthesis 349, 350 Raucher indole synthesis 363, 365, 366 pyrallol[1,2-a]indoles 483, 486 Rawal indole synthesis 361–362 pyrano[3,4-b]indol-3-ones 438, 439 Reissert indole synthesis 332–337 pyridazinoindoles 284 solid-phase synthesis 370, 376, 378 pyrolysis 278–286 Yao carbazolone synthesis 371, 373 see also flash volume pyrolysis Reissert indole synthesis 332–337 pyrroles applications 332–335 aryne intermediates to indoles and carbazoles 528–536 indoles produced 334 catalytic dehydrogenation 520–524 mechanism 332 cycloaddition syntheses from vinyl pyrroles 506–511 Minutolo N-hydroxyindole synthesis 336, 337 electrocyclization 512–516 modern Reissert indole syntheses 334–335 electrophilic cyclization 495–502 modifications 334–337 miscellaneous indole ring-forming syntheses 525–527 N-hydroxyindoles 335–337 palladium-catalyzed cyclization 503–505 Nicolaou N-hydroxyindole synthesis 335–337 photocyclization of pyrrole analogues of stilbene 473, 478 Remers indole synthesis 520, 521 pyrrolidine 338–341 reverse-Madelung indole synthesis pyrrolocoumarins 98 Couture indole synthesis 174–175 pyrrolo-2,3-quinodimethanes 517–519 Jones–Schmid indole synthesis 165–173

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reviews of indole-ring synthesis 32–34 SET see single-electron transfer general reviews 32 Shafiee indole synthesis 451, 453, 457 indole analogues 34 Sha indole synthesis 447, 449, 517–518 microwave-promoted indole ring synthesis 33 Shannon indole synthesis 512, 513 miscellaneous reviews 33–34 Shi indole synthesis 483, 486 name reactions 33 sigmatropic rearrangements solid-phase indole ring synthesis 32–33 Bartoli indole synthesis 121–130 specialized reviews 32–33 Burger indole synthesis 140, 143 specific indoles 33 Fischer indole synthesis 41–115 specific reactions 33 Gassman indole synthesis 116–120 synthesis of carbazoles, carbolines, and indolocarbazoles 34 Hwu indole synthesis 139, 142 rhodium-catalyzed indole ring synthesis 632–639 Julia indole synthesis 137–138 Driver indole synthesis 633, 636 Martin indole synthesis 139, 141 early indole syntheses 632, 633 miscellaneous cycloaddition reactions 487–491 Fagnou indole synthesis 632, 634 miscellaneous sigmatropic rearrangements 139–143 Fischer indole synthesis 44–45 Oikawa, Yonemitsu indole synthesis 139, 140 Glorius indole synthesis 632, 635 Parsons indole synthesis 139, 142 Huang indole synthesis 632, 635 Pinna indole synthesis 139, 141 Lautens indole synthesis 632, 635 Saczewski indole synthesis 139, 141 miscellaneous indole ring-forming syntheses 634–635, 637 Thyagarajan indole synthesis 131–136 Moody indole synthesis 634, 638 Wojciechowski indole synthesis 139–140, 142 Nakamura indole synthesis 634, 638 silver-catalyzed indole ring synthesis 651–653 pyrroles 526 single-electron transfer (SET) pathway 396, 655, 657 reductive cyclization 363, 365 Smith carbazole synthesis 477, 479 Saito indole synthesis 632, 634 Smith indole synthesis 181–185 Trost indole synthesis 632, 634 applications 181, 183–184 Witulski indole synthesis 632, 634 indoles produced 185 ring-closing metathesis 646–647 mechanism 181, 182 rizatriptan 545, 607 Snyder indole synthesis 349, 350, 447–448, 450 Rossi indole-carbazole synthesis 474, 479 sodium borohydride 244–245, 558, 559 ruthenium-catalyzed indole ring synthesis 645–647 solar cells 26–27 carbazoles 646 solid-phase synthesis carbolines 646 Fischer indole synthesis 56–57, 60 Grubbs catalysts 646–647 Larock indole synthesis 612 intramolecular amination 646 Madelung indole synthesis 148, 153 ring-closing metathesis 646–647 reductive cyclization 370, 376, 378 Watanabe indole synthesis 383, 384, 385, 389 reviews of indole-ring synthesis 32–33 Wittig–Madelung indole synthesis 158, 163 Saá indole synthesis 454–455, 459 Somei 1-hydroxyindole synthesis 343–344 Saczewski indole synthesis 139, 141 Somei N-hydroxyindole synthesis 546, 548–549 Saegusa indole synthesis 221–227 Sommelet–Hauser rearrangement 116 indoles produced 225 Srinivasan indole synthesis 447, 450 mechanism 221, 222 SSRI see selective serotonin reuptake inhibitors modifications 221–226 statins 18 Zeech indole synthesis 223, 226 Steck indole synthesis 193–194, 198, 199 Saito indole synthesis 520, 522, 632, 634 Stephen and Walker indole synthesis 349, 350 samarium diiodide 414 Stevens indole synthesis 165, 169 Sanz indole-carbazole synthesis 531, 532 Stevens–Opatz indole synthesis 165, 169 scandium-catalyzed indole ring synthesis 666, 667 stilbene pyrroles 473, 478 Schmittel indole synthesis 478, 479–480 stobadine 12 Schulte indole synthesis 560–561 Stoltz indoline-indole synthesis 535 Schultz indoline-indole synthesis 471, 477 Studer indole synthesis 533, 534 Seitz indole synthesis 506, 508 Sugasawa indole synthesis 244–245 selective estrogen-receptor modulators (SERM) 16 sulfinamides 137–138 selective serotonin reuptake inhibitors (SSRI) 21 sulfonium ylides 232, 234 selenium-catalyzed dehydrogenation 548, 549–550 sumatriptan 8, 69–70 Selvakumar indole synthesis 230, 232, 233 Sundberg indole synthesis 278–286 semicarbazones 342–343 applications 278–282 SERM see selective estrogen-receptor modulators carbazoles 278–280, 282, 284–285 serotonin (5-HT) receptors dictyodendrins 280, 282 biological activity of indoles 7–8, 9 fused indole heterocycles 280, 283, 284 Fischer indole synthesis 69–72 indoles produced 281 pharmaceutical indole products 18–19, 21 mechanism 278–280, 284–285

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modifications 284–285 tryptophans 90, 93 Tokuyama indole synthesis 280, 282 tubulin 10, 11, 76–77 Suzuki coupling reactions 271, 280 tungsten-catalyzed indole ring synthesis 666, 667

Taber indole synthesis 296–298 Utimoto indole synthesis 615, 616 Tao indole synthesis 507, 508 tartric acid–dimethylurea melt 41 vancomycin-resistant Enterococcus faecalis (VRE) 76 Täuber carbazole synthesis 301–303 van Leusen indole synthesis 512, 513 Cho carbazole synthesis 302–303 Vedejs indole synthesis 483, 485, 512, 513 Leditschke carbazole synthesis 301–302 Velezheva indole synthesis 194, 197 modifications 301–303 vicarious nucleophilic substitution (VNS) 349, 354, 358–359 Olah carbazole synthesis 302–303 Vidal indole synthesis 483, 486 TDAE see tetrakis(dimethylamino)ethylene Vilsmeier reagent 317–318, 320 telomerase 27 Vilsmeier–Haack reagent 344–345 tetrakis(dimethylamino)ethylene (TDAE) 412–413 vinyl pyrroles 506–511 tetramethylethylenediamine (TMEDA) 181 viral infections 5–6, 7, 19–20, 75–76 TFA see trifluoroacetic acid VNS see vicarious nucleophilic substitution TFAA see trifluoroacetic acid anhydride VRE see vancomycin-resistant Enterococcus faecalis thermolysis Graebe–Ullmann carbazole-carboline synthesis 424–426 Wacker indole synthesis 148, 153 Hemetsburger indole synthesis 287–295 Wang indole synthesis 416, 422 Taber indole synthesis 296–298 Wasserman indole synthesis 455, 459 Thesing indole synthesis 553, 554 Watanabe indole synthesis 383–390 thioanilides 405, 407 applications 383 Thyagarajan indole synthesis 131–136 indoles produced 388 applications 131 iridium-based indole synthesis 383, 387 indoles produced 135–136 mechanism 383, 384 Majumdar synthesis 131, 135 modifications 383, 386–389 Makisumi and Takada synthesis 131, 133 new catalytic systems 383, 385, 387 mechanism 131–132 synthesis of teleocidin analogues 389 tin-mediated cyclization Xing and Liu indole synthesis 383, 386 Fukuyama indole synthesis 405–408 Zhang and Ding indole synthesis 383, 386 imidoyl substrates 409 Watanabe–Cenini–Söderberg indole synthesis 604–606 indolines 410 applications 604, 606 miscellaneous syntheses 409–411 mechanism 604, 605 titanium-catalyzed indole synthesis 45–46, 361 Weber indole synthesis 512, 513 TMEDA see tetramethylethylenediamine Welch indole synthesis 446–447, 449 Tobinaga indole synthesis 520, 522 Wender indole synthesis 176–180 Togni reagent 414 indoles produced 178 Tokuyama indole synthesis 280, 282 mechanism 176, 177 Tokuyama indoline-carbazole synthesis 531, 532 modifications 176, 179 Török indole synthesis 500, 501 Nicolaou tryptamine synthesis 176, 179 Townsend indole synthesis 512, 513 Willis indole synthesis 619, 620 transesterification reactions 219–220 Wipf indole synthesis 458, 460 trialkyl phosphites 266–267, 269, 271–272 Wittig olefination–Claisen rearrangement 366 1,2,3-triazoles 425, 430 Wittig–Madelung indole synthesis 156–164 tricyclic indoles 13–14 applications 156, 158 triethyloxonium tetrafluoroborate 137–138 Hughes solid-phase synthesis 158, 163 trifluoroacetic acid anhydride (TFAA) 260 Imamoto indole synthesis 156–157, 160 trifluoroacetic acid (TFA) 260 Imaniski indole synthesis 156, 159 triphenylamine 468, 470 Kraus indole synthesis 157, 161–162 triphenyl phosphite 269, 271 mechanism 156, 157 triptans 18 modifications 156–163 eletriptan 72 Pindur indole synthesis 156, 159 rizatriptan 18, 545, 607 Witulski indole synthesis 454, 459, 632, 634 sumatriptan 8, 18, 69–70 Wojciechowski indole synthesis 139–140, 142 Troschütz indole synthesis 194, 201 Wright indoline synthesis 219–220 Trost indole synthesis 496, 498, 632, 634 Wu indole synthesis 489, 490 Truce–Smiles rearrangement 371 Würthwein indole synthesis 489, 490 tryptamines Wu-Sha indole synthesis 534–535 Fischer indole synthesis 90, 93 Hemetsburger indole synthesis 288 Xiao indole synthesis 487, 488 Wender indole synthesis 176, 179 Xing and Liu indole synthesis 383, 386

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Yamada indoline-indole synthesis 471, 477 Zeech indole synthesis 223, 226 Yamanaka–Sakamoto–Sonogashira indole synthesis Zhang and Ding indole synthesis 383, 386 607–610 Zhou indole synthesis 396, 398, 399 applications 607–609 Zhu indole synthesis 533, 534 indoles produced 609 zinc-catalyzed indole ring synthesis 651–654 mechanism 607, 608 Leimgruber–Batcho indole synthesis 338–340 Yamashita indole synthesis 507, 509 Nenitzescu o,β-dinitrostyrene reductive cyclization 325 Yao carbazolone synthesis 371, 373 Pschorr–Hoppe indole synthesis 352 yatakemycin 464, 467 ZipA–FtsZ interaction 77 Yoshida-Yanagisawa indole synthesis 509, 510 zirconium catalyzed indole ring synthesis 56 Yu indole synthesis 256 Zyryanov indoline-indole synthesis 535

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