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Copyrighted Material Index α-Effect 20 Advair 645 ‘α-Position’, in names 1 Agonists 646 ‘β-Position’, in names 1 AICA see 5-aminoimidazole-4-carboxamide Abiraterone 657 Alcoholic fermentation 632 ACE inhibitors 655 Aldehyde synthesis, using thiazoles 466 4-Acetamidobenzenesulfonyl azide 105 Alkaloids 637, 638 Acetazolamide 656 Alkyl radicals, generation 29 Acetyl hypofl uorite 609 N-Alkylation of azoles 30 1-/2-Acetyl-1,2,3-triazole 558 N-Alkylation, unambiguous via O-silyl-derivatives 267 Acetylcholine 652 3-Alkylidene-3H-indoles 382 1-Acetylindole 376 Allosteric binding 646 reaction with MoOPH 385 Alosetron 654 3-Acetylindole 376 Alprazolam 658 1-Acetylindoxyl, Wittig reaction 398 Alzheimer’s disease 658 2-Acetylthiophene 327 Ambien 658 Achmatowicz rearrangement 351 Amias 655 Acidity of C-hydrogen in 5-membered heterocycles 40, 42 Amidines, synthesis from 1,2,4-oxadiaxoles 571 Acidity of C-hydrogen in 6-membered heterocycles 42 α-Amino acids 629, 640 Acidity of C-hydrogen, factors infl uencing 38 deamination 631 Acidity, defi nition 19 decarboxylation 631, 632 Activated zinc 47 a 2-Amino-1,3,4-oxadiazole 570 Activating substituents for electrophilic substitution 22, 23 a 5-Amino-1,2,4-thiadiazole 570 Active pharmaceutical ingredient 649 3-Amino-1,2,4-triazole 560 Acular 656 Amino-1,3-azoles, basicity 471 Acyclovir 661 γ-Aminobutyric acid 647 Acyl radicals, generation 28, 29 Aminocarbonyl radicals, generation 28 1-Acyl-benzotriazoles, use in N-acylation of pyrrole 299 2-Aminoimidazole 471 3-Acylindoles, reduction to alkyl 396 ring synthesis 475 C-Acylpyrroles, 2/3-rearrangement 309 5-Aminoimidazole-4-carboxamide, in pyrimidine synthesis Additives, for Pd(0)-catalysis 61 532, 533 Adenine 516, 527, 635 a 3-Aminoindole, as acetamide 375 from 2-chloropurine 522 COPYRIGHTEDAmino-indoles, MATERIAL tautomerism 400 ring-opening 519 1-Aminoindolizines 542 ring synthesis Amino-isoquinolines, basicity 185 from 4-chloropyridine-5,6-diamine 532 3-Aminoisoquinoline 181 from HCN plus NH3 534 4-Aminoisothiazole, diazotisation 493 Adenosine 515, 636 5-Aminolevulinic acid 634, 664 N-alkylation 516 Aminomalononitrile, in oxazole ring synthesis 475 notable purine synthesis 534, 535 Aminopurines, conversion into halides 529 15N-1- 617 diazotisation 528 Adrenaline 647, 654 tautomerism 525 Adrenergic receptors 654 Amino-pyrazines, basicity 271 Heterocyclic Chemistry 5th Edition John Joule and Keith Mills © 2010 Blackwell Publishing Ltd 666 Index 2-Aminopyrazine, diazotisation 272 Arylboronic acids from Chichibabin reaction 256 in Cu-catalysed azole N-arylations 86, 87 2-Aminopyrazole, Diels–Alder reaction 491 in Cu-catalysed purine N-arylations 87 3-Aminopyrazole, halogenation 493 5-Aryltetrazoles, thermolysis 564 nitration 493 Ascidian 640 ring synthesis from acrylonitrile 495 Ascididemine 639 4-Aminopyridazine, from Chichibabin reaction 256 Aspergillic acid 640, 641 2-Aminopyridine 132, 544 Aspirin 655 3-Aminopyridine 133 Atomic carbon 564 Amino-pyridines, acylation 145 Atorvastatin 645, 656 N-alkylation 145 ATP 515, 636, 637 basicity 144 Atrazine 623 diazotisation 146 Atropine 653 electrophilic substitution, regioselectivity 145 Aureusin 642 halogenation 145 Aurones 642 nitration 145 2-Aza-bicyclo[2.2.0]hexadienes 141 tautomerism 142 (2.2.2)Azacyclazine 552 Amino-pyrimidines, basicity 271 5-Azacytidine 661, 662 1-Aminopyridinium iodide 126 4-, 5-, 6-, 7-Azaindoles 400 2-Aminopyrimidine, bromination 272 basicity 400, 401 4-Aminopyrimidine, from Chichibabin reaction 256 biological 3-alkylation 620 2-Aminopyrimidine-5-boronic acid 272 ring synthesis from ortho-iodo-pyridinamines plus alkynes 2-Aminopyrimidine methiodide, Dimroth rearrangement 421 272 4-Azaindoles, ring synthesis from ortho-nitropyridylacetonitrile Amino-quinolines, basicity 185 422 5-Aminotetrazole 561, 564 6-Azaindoles, ring synthesis from pyrroles 422 diazotisation 564 7-Azaindole, typical reactions 401 ring synthesis 568 N-oxide 401 2-Aminothiazole, halogenation 471 Aza-indolizines 543 3-Aminothiophene-2-carboxylate, methyl 611 basicity 543 Amlodipine 645, 646, 654 Azathioprine 662 Anchimeric assistance in purine glycosylation 518 Azete 597 α-Angelica lactone 357 Azetidines 597 β-Angelica lactone 357 basicity 592 Angiotensin-I and –II 655 ring synthesis Aniline, acidity 11 from X(C3)Y 602 Anomeric affect 590, 591 ring synthesis via 2 + 2 additions 602 ANRORC process 181, 209, 210, 211, 357 Azetidinone, from an isoxazole 489 Antagonists 646 2-Azidopyrimidine 258 Anthocyanins 130 Aziridines 592 colour variation with pH 641, 642 basicity 592 Anticholinesterase agents 653 lithio 599 Antihistamine 650 reaction with nucleophiles 594 Antipyrine 493 removal of N 595 API 649 ring opening reactions 594, 595 Apigenin, notable chromone synthesis 244 ring synthesis Apresoline 654 from alkenes 600, 602 Arachadonic acid amides 647 from X(C2)Y 600 Arancep 645 from imines 601 Arava 657 N-tosyl 594 Aristeromycin, notable purine synthesis 534 Azirines 592 Aromas, natural 640, 641 Diels–Alder reactions 596 Aromatic electrophilic substitution, mechanism 116 ring synthesis from oximes 601 Aromatic nucleophilic substitution, mechanism 117 Azoles, acidity 557 Aromatic resonance energy 6 Azoles, basicity 20, 447 Aromaticity Azoles, mesomeric structures 11 benzene 5 1,2-Azoles naphthalene 6 electrophilic substitution, regioselectivity 456 pyridine 7 nucleophilic substitution, regioselectivity 456 Index 667 ring synthesis from R(C=O)(C)(C=O)R plus H2NZH 459 Benzo[b]pyryliums 205, 229 typical reactivity 456 ring synthesis from ArOH plus R(C=O)(C)(C=O)R 1,3-Azoles 207 C-hydrogen exchange 464 Benzo[b]thiophenes 369 N-alkylation, relative rates 462 2-lithiation 371 electrophilic substitution, regioselectivity 456 Benzo[c]furans 369, 447 lithiation, regioselectivity 457 Diels–Alder reaction 372 nucleophilic substitution, regioselectivity 456 Benzo[c]pyrylium 229 ring synthesis Benzo[c]thiophenes 369, 447 from R(C=O)(C)Hal plus H2N(C)(C=Z) 458 Diels–Alder reaction 372 from TsCH2NC plus R(C=Z)H 458 ring synthesis typical reactivity 455 from thiophenols 372 ylides 464 from phthalides 450 1,3-Azole acids, decarboxylation 464 from thiophenes 450 1,3-Azole N-oxides 473 Benzo-1,2-azoles, typical reactivity 458 AZT 661 Benzo-1,3-azoles, typical reactivity 458 Azulene, synthesis from Zincke’s salt 153 Benzoin condensation 471 Benzopyrones Baeyer-Villiger oxidation 230 electrophilic addition to oxygen 232 Balz-Schiemann reaction 611 electrophilic substitution 232 Barbiturates 263, 659 halogenation 232 Barbituric acid 263 1H-2-Benzopyran-1-one 229 Bartoli synthesis of indoles 412 2-Benzopyran-3-ones, Diels–Alder reaction 236 Barton-Zard synthesis of pyrroles 315 2H-1-Benzopyran-2-one 229 Base pairing in nucleic acids 635, 636 3H-2-Benzopyran-3-one 229 Basicity, defi nition 19 4H-1-Benzopyran-4-one 229 Batch processes 104 nitration 232 Baycol 656 Benzopyrylium ions, addition of ammonia 230 BEDT-TTF 1-Benzopyrylium ions 229 Benetex® OB 625 addition of carbon nucleophiles 231 Benzene addition of silyl enol ethers 231 mesomeric structures 6 ring synthesis orbital picture 6 from ArOH plus R(C=O)(C)(C=O)R 237, 238 resonance 6 from ArOH plus RC≡C(C=O)R 238 1H-Benzimidazole see Benzimidazole from ortho-Ar[OH][C=O)R] plus RCH2(C=O)R 237 Benzimidazoles 503 2-Benzopyrylium ions 229 acidity 505 ring synthesis from ortho-Ar[C=O][CH2(C=O)R] 242 N-acylation 504 Benzothiazoles 503 basicity 503 2-metallation 505, 507 bromination 504 2-nucleophilic substitution 505 2-metallation 505 ring synthesis 2-nucleophilic substitution 505 from ortho-Ar[SR][(C=O)R] 459 ring synthesis using 1,3,5-triazine 576 from Ar(NH)(C=S)NHR 509 ring synthesis from ortho-Ar[NH2][SH] plus RCO2H 507, 508 from ArN=CNH2 509 a Benzo[b]thiophene 2,3-quinodimethane 33 from ortho-Ar[NH2][NH2] plus RCO2H 507, 508 Benzo[c]thiophenes, synthesis from dihydrobenzo[c]thiophene N-substitutions 505 S-oxides 450 Benzimidazole-2-thiol 504, 505 Benzothiophenes, 2,3-dihydroxylation 620 1,2-Benzisothiazole 503 Benzotriazole 579–581 2,1-Benzisothiazoles, ring synthesis from ortho-Ar[Me][NH2] N-arylation 581 plus SOCl2 512 displacement with Grignard reagents 580 1,2-Benzisoxazoles 503 leaving group in VNS processes 580, 581 ring synthesis from ortho-Ar[Hal][(C=NOH)R] 509, 510 use in cyclopropane synthesis 580 2,1-Benzisoxazoles, ring synthesis from ortho-Ar[N3][(C=O)R] use in 1,4-diketone synthesis 580 511 use in ene-one synthesis 580 Benzo[1,2-b:4,3-b′]-dipyrroles, notable pyrrole synthesis 318 use in general synthesis 579 Benzo[b]furans 369 use in peptide synthesis 580 2-lithiation 371 use in stabilising cations 580 ring synthesis from phenols 372 Benzotriazoles, conversion into other heterocycles 581 668 Index Benzoxazoles 503 3-Bromoisoquinoline, conversion into 3-aminoisoquinoline 181 2-metallation 506 3-Bromo-2-pyrone, in Diels–Alder reactions 217 2-nucleophilic substitution 505 5-Bromo-2-pyrone, in Diels–Alder reactions 217 ring synthesis from ortho-Ar[NH2][OH] plus RCO2H 507, 4-Bromopyrazole 488 508 halogen-metal exchange 490 Benzyl isonitriles, preparation 564 2-Bromopyridine 134 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride 471 3-Bromopyridines 137 Bergamotin 657, 658 nucleophilic displacement of bromine 133, 134 Biginelli synthesis of dihydropyrimidinones 278 3-amination 86 with ionic liquid tag 102 5-Bromopyrimidine 255 Bilirubin 635 halogen-metal exchange 250, 260 Biotin 633 Minisci reaction at C-4 261 2,2′-Bipyridyl 60 3-Bromoquinoline, halogen-metal exchange 182 Birch reduction 139, 140, 307, 353, 392 5-Bromoquinoline, halogen-metal exchange 182 Bis(pinacolato)diboron 50 2-Bromothiophene
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