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Nonclassical Imcrs

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Nonclassical Imcrs 587 Index a acyl halides 52–55 ab initio calculations 24, 40, 41 O-acyl isoimides 49–51 Acantkella acuta 21 S-acyl isoimides 50, 51 acetals 188, 189, 401 acyl transfer reactions see Mumm acetylenedicarboxylates rearrangements – nonclassical IMCRs 315, 316 acylating agents 129–133 – zwitterions 264–267, 269, 271, 274–277 2-acylbenzazepines 54 achiral isocyanides 1 1-acyl-3,4-dihydroisoquinolines 54 acid addition reactions 49–52 α-acyloxyaminoamides 367 acid-mediated polymerization 25 acylpiperazines 352 acid-promoted condensations 355 2-acylpyrrolines 54 α-acidic isocyanides 75–108 acylthioamides 53, 54 – dihydropyridone MCR 95–97 2-adamantyl isocyanide 37 – 4,5-disubstituted oxazole MCR 83, 84 ADC see acyclic diaminocarbenes – 2-imidazoline MCR 91–95 AFM see atomic force microscopy – isocyanide reactivity 78–80 AIBN see azo-bis-isobutyronitrile – multicomponent reactions 75–108 alcohols – nitropyrrole MCR 83, 84 – carbene coupling reactions – oxazole MCR and in situ Domino process 532–537 88–91 – chiral nonracemic isocyanides 2 – synthesis 76–78 – isocyanide reactivity 64–66 – 2,4,5-trisubstituted oxazole MCR 84–88 – zwitterions 273–275 – 2,6,7-trisubstituted quinoxaline MCR 82, aldazines 204 83 aldehyde-acids 362, 366–371 – union of MCRs 93–95 aldehydes – van Leusen imidazole MCR 81, 82 – amine surrogates 199 acrylonitriles 116 – carboxylic acid surrogates 180–184 activated alkenes – chiral nonracemic isocyanides 4, 5 – isocyanide reactivity 55–58 – isocyanide reactivity 58–60 – α-isocyanoacetic acid derivatives 116, – α-isocyanoacetic acid derivatives 116, 117 121–126, 141, 142 – pyrrole synthesis 386–390 – nonclassical IMCRs 305, 317 – zwitterions 279–281, 284–286, 288 – zwitterions 275, 276, 283 activated alkynes 55–58, 390 aldol reactions 18, 121–126 activated azines 220–223 alginate-coated gold electrodes 241, activated heterocumulenes 60, 61 242 activated isocyanides 299, 308–320 aliphatic isocyanide reactivity 36–41, acyclic diaminocarbenes (ADC) 531–533, 43–46, 52 537, 546 aliphatic nitriles 37–39 Isocyanide Chemistry: Applications in Synthesis and Material Science, First Edition. Edited by Valentine Nenajdenko. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2012 by Wiley-VCH Verlag GmbH & Co. KGaA. 588 Index alkenes amino isocyanides 11, 12 – isocyanide reactivity 55–58 N-aminolactams 214 – pyrrole synthesis 386–390 5-aminooxazoles 140, 141 – zwitterions 279–281, 284–286, 288 2-amino-4H-pyrans 270 5-alkoxyoxazoles 80 2-aminopyrazoles 466 alkyl isocyanoacetates 109, 110 aminopyrroles 278, 279 alkyl 2-nitroethanoates 268 5-aminothiazoles 132 alkyl phenylglyoxylates 316 anthracenes 410, 411 alkylamines 281 anti-fouling activity 20, 21 N-alkylated quinolines 220, 221 antitubulin chalcones 471 alkylation reactions 113–115, 351, 352 Arbuzov reactions 10 alkyne–azide cycloaddition reactions arenesulfenyl chlorides 138 442–444 Armstrong benzodiazepine synthesis 433 alkynes aromatic nitro compounds 402–407 – isocyanide reactivity 55–58 aromatic substitution reactions 355, 356 – α-isocyanoacetic acid derivatives 119–121 aryl transfer reactions see Smiles – pyrrole synthesis 390, 401, 402 rearrangements – zwitterions 263–282 N-aryl amidation reactions 437, 438 allylation reactions 114 N-aryl arylimines 64 alternating peptoid–peptide chimeras 253 N-aryl carboxamides 171, 172 ambiguine H 22, 23 aryl isocyanide reactivity 36, 39–41, 43–46, amides 50, 51, 271–273 52, 53, 65 amidines aryl nitriles 39, 40 – carbene coupling reactions 538, 539 arylsulfenyl chlorides 55 – carboxylic acid surrogates 179, 184 arylsulfonylmethyl isocyanides 76–80 – chiral nonracemic isocyanides 15 N-aryl thiocarboxamides 175, 176 – molecular diversity 371–373 arynes 283, 284, 316–318 – nonclassical IMCRs 324 Asinger reactions 362 aminals 188, 189 atomic force microscopy (AFM) amine surrogates 195–231 – chiral nonracemic isocyanides 26 – activated azines 220–223 – polyisocyanides 558, 563, 567, 572 – enamines, masked imines and cyclic atropisomerism 23, 557 imines 223–227 Axinella cannabina 18 – hydrazines 200–218 axisonitrile-1 16 – hydroxylamines 196–200 axisonitrile-3 18 – isocyanide reactivity 220–223 aza-Diels–Alder reactions 89, 90 – miscellaneous surrogates 218–220 1-azadienes 269 amines 6-azaindolines 89, 91 – carbene coupling reactions 532–537 aza-β-lactams 212 – chiral nonracemic isocyanides 2, 3 azasugar imines 225, 226 – isocyanide reactivity 64–66 aza-Wittig reactions 358, 359, 439, 440 – zwitterions 264 azepine tetrazoles 170 amino acids azetidinones 186 – amine surrogates 203 azides – α-isocyanoacetic acid derivatives 111 – amine surrogates 226 – molecular diversity 362–365 – chiral nonracemic isocyanides 11, 12 – polyisocyanides 563 – polyisocyanides 570, 571 α-aminoaldehydes 436, 437 – tetrazole synthesis 471–473 aminoboranes 184 2-azidophenyl isocyanide 540 aminocarbenes see carbenes azines N-aminocarbonyl amides 218 – amine surrogates 220–223 amino carboxamides 182 – nonclassical IMCRs 300, 304–306 aminocarbynes 532 azinium salts 300 2-aminofurans 451–453 azoalkenes 206 Index 589 azo-bis-isobutyronitrile (AIBN) 14, 47 – tethered aldehyde and keto acids 362, azolium salts 306 366–371 azomethines 59, 60, 310–312 – tethered heterocyclic amidines 371–373 Biginelli reactions 76 b binucleation of mononuclear ligands 515, Barton–Zard pyrrole synthesis 116, 117, 516 386, 390–410, 420–424, 458 biocatalytic desymmetrization 13 base-promoted condensations 355 bioconjugates 240, 241, 258 BBN see 9-borabicyclononanes biomimetic syntheses 20, 21 BCOD see bicyclo[2.2.2]octadiene bipyrroles 396, 397 benzamides 284 bis(aminofuryl)bicinchoninic amides 274, benzazepines 342, 343 275 benzhydrylium ions 36 Bischler–Napiralski synthesis 48 benzimidazoles 2,3-bis-iminoazetidines 59, 60 – IMCR examples and protocols 473 block copolymers – molecular diversity 338, 340, 341, 345 – chiral nonracemic isocyanides 26 benzimidazolium salts 307, 308 – polyisocyanides 556, 557, 565, 574 benzochromenes 274 BODIPY see boron–dipyrromethene 1,5-benzodiazepine-2,4-diones 443–446 bond-forming effi ciency 336 1,4-benzodiazepine-2,5-diones (BZD) 9-borabicyclononanes (BBN) 22, 23 337–339, 345, 433–439 boron–dipyrromethene (BODIPY) dyes benzodiazepines 431–449 385, 386, 391, 420–424 – 1,4-benzodiazepine scaffolds via IMCRs boron trifl uoride 186 433–443 borylative cyclization reactions 326 – 1,5-benzodiazepine scaffolds via IMCRs bovine serum albumin (BSA) 240, 241 443–446 bridging ligands – fused-ring systems 440–443 – carbenes 534, 535 – molecular diversity 337–340, 343–347, – isocyanoarenes 494, 495, 514–517 349, 350 2-bromobenzoic acids 437 – two-ring systems 433–440 β-bromo-α-isocyanoacrylates (BICA) 135, benzodiazepinones 353, 359, 437, 438, 445 136 benzofurans 473 Brønsted acids benzofused heterocycles 175, 176 – carboxylic acid surrogates 180, 181, 187 benzofused γ-lactams 366, 367 – molecular diversity 372 benzopiperazinones 176, 177, 357 BSA see bovine serum albumin benzoporphyrins 410 BTPP see t-butyl-iminotris(pyrrolidino) benzoquinones 317 phosphorane 1,4-benzothiazepines 368, 369 Burgess reagent 2 benzoxazepines 342, 343 butylated hydroxy toluene (BHT) 393 benzoxazepinones 353 t-butyl-iminotris(pyrrolidino)phosphorane benzoxazinones 351, 353 (BTPP) 401, 403, 404 benzoyl isothiocyanate 280, 281 BZD see 1,4-benzodiazepine-2,5-diones benzyl isocyanide 38 BHT see butylated hydroxy toluene c BICA see β-bromo-α-isocyanoacrylates carbamoylated dihydroisoquinolines 301 bicyclic lactams 338, 339, 358, 364, 373 carbenes bicyclic tetrazoles 343, 344 – amine and alcohol coupling reactions bicyclo[2.2.2]octadiene (BCOD) 385, 386, 532–537 409, 410, 414–416, 419, 423, 424 – dipole–isocyanide couplings 543, 544 bifunctional approach (BIFA) 361–374 – functionalized amine and alcohol – amino acids 362–365 couplings 537 – combined bifunctional and post- – hydrazine and hydrazone couplings 537, condensation modifi cations 373, 374 538 – cyclic imines 362, 365 – imine and amidine couplings 538, 539 590 Index – intramolecular cyclizations 536, 537, chiral polyisocyanides 551–553 540–543 chiral racemic isocyanides 1 – α-isocyanoacetic acid derivatives 122, chiral stationary phases (CSP) 572 128 chlorination reactions 22, 53 – metal-bound isocyanides 531–550 chlorination–elimination strategy 226 – miscellaneous reactions 544–546 α-chloroketones 173, 174 – polyisocyanides 554 cholanic peptide–steroid hybrids 239, 240 – reactivity modes 531, 532 chromenes 274 carbonic acid derivatives 163–165 chromenylfurandicarboxylates 277 carbonimidyl chlorides 52, 53 chromium complexes carbonylmetalate complexes 493–497, – carbenes 540 502–505, 514, 515 – isocyanoarenes 511–516, 519–521 carboxamides 368–370 chromophore-functionalized polyisocyanides carboxylation reactions 110 563–570 carboxylic acid surrogates 159–194 cinchona alkaloid catalysts 117 – carbonic acid derivatives 163–165 circular dichroism (CD) spectroscopy – cyanamide 179 – chiral nonracemic isocyanides 24, 26 – hydrazoic acid 167–171 – polyisocyanides 557–559, 561–563, 565, – isocyanic acid derivatives 166, 167 570, 573, 574 – mineral and Lewis acids 180–189 Claisen rearrangements 18, 77 – phenols and derivatives 171–179 click chemistry 361, 569–572 – selenide and sulfi de 165, 166 cobalt complexes – silanol 165, 166 – α-isocyanoacetic acid derivatives 126 – thiocarboxylic acids 160–163 – isocyanoarenes 497–501, 522 carboxylic acids collagenase-I 340, 341 – chiral nonracemic isocyanides 2 compound chemical tractability 336 – isocyanide reactivity 49–52 concanavalin A 237 – zwitterions 274, 275 conformation memory 560, 561 carvone
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