198 Index
COX enzymes, see Cyclooxygenase enzymes
COX-1/-2 activity 174
Crestor 167
Cross-coupling to form C–N bonds 27
Cross-coupling to form C–S bonds 27
Cyanoacetamide, in pyridone ring synthesis 45, 46
Cyanocobalamin, see Vitamin B 12
Cyanuric acid 139
(3.2.2)Cyclazine 148, 149
(3.3.3)Cyclazine 149
Cyclazine, a bis(methoxycarbonyl)-, from indolizine 144
Cyclic adenosine monophosphate 123
Cyclic guanosine monophosphate 123
Cycloadditions, [3 2] 20
Cycloadditions, [4 2] 19
Cycloguanil 175, 176
Cyclohexene, 1-methyl-, epoxide, reaction with methoxide and
MeOH 151
Cyclohexene epoxide
reaction with BnNH 2 151
reaction with n-Bu 3 SnN 3 151
reaction with LiCH 2 CN 151
reaction with Me 2 NH 151
reaction with nucleophiles 151
reaction with strong base 151
Cyclooxygenase enzymes 174
Cyclopentadienyl anion, structure 6, 7
Cysteine, H 2 S from 189
Cytidine 48
Cytosine (C) 48, 164
DADNPO, see 3,5-Diamino-2,6-dinitropyridine N-oxide
DAF, see 3,4-Diamino-1,2,5-oxadiazole
dba, see Dibenzylideneacetone
DCC, see Dicyclohexylcarbodiimide
-Defi cient heterocycle 5
DDQ, see 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Delavirdine (Rescriptor) 177
Delphinidin 3-O-glucoside 166
de novo Ring synthesis, see Heterocyclic ring syntheses
2,6-Deoxyfructosazine 188, 189
3-Deoxyglucosone 187
Deoxyguanosine 122
2-Deoxyribose 122, 164
Di(thien-3-yl)sulfi de, from 3-lithio- 101
Diabetes 189
1,2-Diamines, in ring synthesis of pyrazines 59
Diaminomaleonitrile, in ring synthesis of pyrazines 60
Diamox 175
Diazadienes 19
Diazatetrazole 185
Diazepam (Valium) 173
Diazines
addition of Grignard reagents 50
addition of organolithium reagents 50
amino- 57, 58
cycloaddition reactions 54, 55
disconnections for ring synthesis 58
electrophilic substitution 49, 50
Grignard reagents, preparation 53
halo-, reactions with nucleophiles 51
relative rates of nucleophilic substitution 51
N-oxides 57
metallation 52
radical substitution 52
structure 6
Diazinon 183
Diaziridine 152
Diazoalkanes, in ring synthesis of pyrazoles 121
Diazona chinensis 166
Diazonamide A 166
Diazoxide (Proglycem) 173
Dibenzylideneacetone (dba) 22
1,2-Dibromo-2,2,3,3-tetrafl uoroethane, in bromination 15
1,2-Dichloroethyl ethyl ether, synthetic equivalent of
chloroethanal 117, 118
1,2-Dicarbonyl compounds, in ring synthesis of pyrazines
59, 60
1,3-Dicarbonyl compounds
in ring synthesis of 1-benzopyrylium 76
of coumarins 76
of quinolines 67, 68
of furans 105
of pyrazoles 119
of pyrimidines 58
synthetic equivalents 19, 44, 46
1,4-Dicarbonyl compounds
in ring synthesis of furans 105
of oxazoles 117
of pyrazines 58
of pyrroles 83
of thiophenes 105
1,5-Dicarbonyl compounds
in ring synthesis of pyridines 44, 45
of pyryliums 74, 75
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) 50
1,2-Dichloroethyl ethyl ether, synthetic equivalent of
chlorethanal 117, 118
Dicyclohexylcarbodiimide 117
2-Dicyclohexylphosphino-2,6-dimethoxybiphenyl
(SPhos) 23
Didemnum sp. 166
Diels–Alder reactions 19, 20, 40, 53, 54, 55, 74, 82, 93, 103, 104,
114, 115, 135, 139, 141
Diethyl malonate, in ring synthesis of a pyrimidinone 59
N,N-Diformylhydrazine, synthetic equivalent 136
N,N-Dimethylformamide (DMF), in Vilsmeier reactions 12
N,N-Dimethylformamide azine in ring synthesis of
1,3,4-thiadiazoles 139
of 1,3,4-triazoles 136
Difl ucan 176
2,5-Dihydro-2,5-dimethoxyfuran, synthetic equivalent of
but-2-ene-1,4-dial 19, 99
Diketopiperazines, ring synthesis 60
5,5-Dimethoxypentan-2-one, from 2-methylfuran 100
3-Dimethylamino-ene-ones, synthetic equivalents of
1,3-diketones 19
Dimethylformamide dimethyl acetal (DMFDMA) 44
in Leimgruber-Batcho indole synthesis 95
in ring synthesis of a pyrazole 120
reaction with acidifi ed methylene, mechanism 17, 18
Dimroth rearrangement 57, 124, 129
4,6-Dinitrobenzofuroxan, see 4,6-dinitro-2,1,3-benzoxadiazole
Diovan 168