Copyrighted Material
Total Page:16
File Type:pdf, Size:1020Kb
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. 0002738046.indd 676 5/23/2016 9:12:49 AM Index 677 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 0002738046.indd 677 5/23/2016 9:12:49 AM 678 Index 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