Heterocyclic Chemistry at a Glance

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Index 197

2,2-Bis(diphenylphosphino)-1,1-binaphthyl (BINAP) 22
1,1-Bis(diphenylphosphino)ferrocene (dppf ) 22
Bis(pinacolato)diboron, cross-coupling to introduce
boronate 24
Bischler–Napieralski synthesis of isoquinolines 69
Blood-brain barrier 169
Boc-pyrrole, see 1-(t-Butoxycarbonyl)pyrrole
Body armour 182
Bohlmann–Rahtz synthesis of pyridines 46
Boronic acids from organolithium reagents 15, 16
Boronic acids and esters 15, 16, 23, 24, 30, 38, 39, 53, 54, 66, 80,
81, 91, 92, 101, 102, 113
Brederick’s reagent 18
Bridgehead nitrogen 143
Broad (fava) beans, potential toxicity 192
Bromadiolone 184
Bromination, electrophilic 13
N-Bromosuccinimide 13
BtH, see Benzotriazole
BuLi–LiDMAE 37
But-2-ene-1,4-dial, synthetic equivalent 19, 99
Butane-1,4-dial, synthetic equivalent 19, 99
Butenolide 104
Butyl quinoline secondaire 191


C, see Cytosine
Caffeine 124, 186
Calabar beans 165, 172
Calcium channel blocker 45
cAMP, see Cyclic adenosine monophosphate
Camptosar 178
Camptothecin 178
Caramel 188
Carba nucleosides 123
Carbamoyl radicals 15
Carbazole, 9-phenylsulfonyl- 93
Carbendazim 184
Carbene resonance contributor to 1,3-azolium ylide 113
Carbinolamine 18
-Carboline, 1,2,3,4-tetrahydro-1-benzyl-, from tryptamine 87
3,4-dihydro-1-ethyl-, from N-propionyltryptamine 88
Carbon–nitrogen bonds, formation by cross-coupling 27
Carbon–sulfur bonds, formation by cross-coupling 27
Carbonylation reactions 26, 27
mechanism 29
1,1-Carbonyldimidazole, synthetic equivalent of phosgene 108
Catalysts for palladium(0)-catalysed reactions 21, 22
Catalytic cycle in palladium(0) catalysis 28
Cataracts 189
Catecholamines 169
Celazole-PBI 181
Celebrex 174
Celecoxib (Celebrex) 174
Central Nervous System 169
Cephalosporin 153, 176, 177
cGMP, see Cyclic guanosine monophosphate
Chalcones, in ring synthesis of pyryliums 75
Chan–Lam reaction 30, 56, 111
Chelidonic acid
decarboxylation 75
ring synthesis 75
Chichibabin reaction 35, 50, 64


Chloral in ring synthesis of isatins 97
Chloramine T in ring synthesis of N-tosylaziridines 156
Chloranil for dehydrogenation 68
Chlorination, electrophilic 13
Chloroethanal, synthetic equivalent 117, 118
Chloroiminium electrophile 12
1-(Chloromethyl)-4-fl uoro-1,4-diazoniabicyclo[2.2.2.]octane
tetrafl uoroborate (Selectfl uor) 13
Chlorophyll 82, 162
N-Chlorosuccinimide 13
N-Chlorosulfonamides, in ring synthesis of aziridines 156
Chlorpheniramine (Piriton) 170
Chlorpromazine (Largactil) 174
Chocolate 124, 186
Cholesterol reduction in blood 175
Chromone 73
bromination 73
Mannich substitution 73
nitration 73
2-phenyl-, see Flavone
Chromylium 71
fl ower pigments 165, 166
Chymotrypsin 158, 159
Cimetidine (Tagamet) 170
Cinchona offi cinalis 165
Cinnoline 48
numbering 2
4-Cinnolinone, 3-carboxylic acid, ring synthesis 61
Cipro, see Ciprofl oxacin
Ciprofl oxacin (Cipro) 176
Circadian rhythm 158
Citronellal 191
Clarityn 170
Claviceps purpurea 165
CleviosTM 193
Click reaction 135
Clopidogrel (Plavix) 167
CNS, see Central Nervous System
Collagen 159
Combes synthesis of quinolines 67, 68
Conducting materials, organic 193–194
Coniine 165
Conium maculatum 165
Contact herbicide 183
Copegus 177
Copper phthalocyanine 181
Copper-catalysed amination 30
Copper-catalysed N-arylation
of imidazoles 111
of indoles 89, 90
of purines 126
or pyrazoles 111
of pyrroles 80
Co-trimoxazole 176
Coumalic acid, ring synthesis 76
Coumarins 73
bromination 73
4-bromo-, in Suzuki–Miyaura reaction 24
in hay 166
7-hydroxy-4-methyl-, ring synthesis 76
ring synthesis 191
F&F components 192
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