196 Index
Arylhydrazines for Fischer synthesis, synthesis by cross
coupling 95
Ascididemine 166
Aspergillus sp. 192
Asthma 170
Atorvastatin (Lipitor) 167, 175
ATP, see Adenosine triphosphate
Atrazine 183
Atropine 171, 172
1-Azabicyclo[1.1.0]butane, ring synthesis 155
Azacitidine (Vidaza) 178
(2.2.2)Azacyclazine 149
Azadienes 19
Azafulvenes 82
in porphyrin biosynthesis 163
Azafulvenium 82, 83
Azaindoles, acidities 97
4-Azaindole 97
5-Azaindole 1, 97
6-Azaindole 97
7-Azaindole 1, 97
bromination 98
Mannich substitution 98
nitration 98
reaction with iodomethane 98
reaction with NaH–iodomethane 98
Azaindolizines 145
Azasydnones 138
Azathioprine (Imuran) 178
Azete 3
Azetidines 3, 153
N-trityl-, ring synthesis 155
reaction with HCl 153
2-Azetidinone (-lactam) 153
4-acetoxy-, reaction with azide anion 153
Azide cycloaddition to give 1,2,3-triazoles 136
to an enamine 20
to give tetrazoles 136
Azine, N,N-Dimethylformamide, synthetic equivalent of
N,N-diformylhydrazine 136
1 H-Aziridine, see Aziridine
Aziridines 3, 150
N-aryl-2-methoxycarbonyl-, ring opening to azomethine
ylide 152
2,2-dimethyl-, reaction with HBr 151
2-ethyl-, N-nitrosation and elimination of N 2 O 152
basicity 150
N-ethoxycarbonyl-3-phenyl-, reaction with
Me 2 CuLi 151
2-methoxycarbonyl-1-PMB, ring synthesis 155
ring opening with nucleophiles 151
ring synthesis 155
N-sulfonyl 151
ring synthesis 156
N-tosyl, reaction with cyanoacetate anion 151
2 H-Azirine, see Azirine
Azirine 3, 150
1,1-Azobistetrazole 185
1,2-Azoles
structure 8
disconnections for ring synthesis 119
C–H acidity, regiochemistry 111
1,3-Azoles
C–H acidity, regiochemistry 111
disconnections for ring synthesis 116
structure 8
Azomethine ylides, in -lactam synthesis 157
AZT (Zidovudine) 177Baratol 173
Barbituric acid 55, 173
Barbiturates 55, 173
Basicity, defi nition 9
Benetex OB 181
Benzene, structure 4
Benzimidazoles
acidity 10
basicity 10
numbering 2
1,2-Benzisothiazole, numbering 2
1,2-Benzisoxazole, numbering 2
2,1-Benzisothiazole, numbering 3
2,1-Benzisoxazole, numbering 3
Benzo[b]furan (benzofuran), numbering 2
2-Benzopyryliums 71
1-phenyl-, reaction with NH 3 72
Benzo[b]thiophene (benzothiophene), numbering 2
Benzo[c]thiophene, numbering 2
Benzodiazines 60, 61
Benzo[1,2-b:4,3-b]dipyrroles, ring synthesis 85
Benzofuran-2-boronic acid, cross-coupling with
5-bromopyrimidine 54
Benzophenone hydrazone, use in Fischer indole syntheses 95
1-Benzopyryliums 71
7-hydroxy-2,4-dimethyl-, ring synthesis 76
fl ower pigments 165, 166
2-phenyl-, ring synthesis 76
Benzothiazoles
numbering 2
radical substitution 15
Benzothiophene, 4,5,6,7-tetrahydro-4-oxo-, from
thien-2-yl-(CH 2 ) 3 CO 2 H 100
Benzotriazoles
1-acyl-, as acylating agents 137
1-acyl-, reaction with pyrrole 79
1-amino-, oxidation to give benzyne 137
from benzotriazole 137
reaction with NH 2 OSO 3 H 137
ring synthesis from 1,2-diaminobenzene 140
synthetic auxiliary 136
2,1,3-Benzoxadiazole, 4,6-dinitro- 186
Benzoxazole, numbering 2
Benzyne, generation from 1-aminobenzotriazole 137
Bergamotin 175
Betanin 190
Bidentate ligands 22
BINAP, see 2,2-Bis(diphenylphosphino)-1,1-binaphthyl
Binding
allosteric 168
competitive/non-competitive 168
Biotin, see Vitamin H
2,2-Bipyridine 34
1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-
2-ylidene (IPr) 23