200 Index
Furans (continued )
oxidation 103
reaction with diethyl acetylenedicarboxylate 103
with maleic anhydride 103
resonance energy 8
structure 8
3-trifl uoromethyl-, ring synthesis via Diels–Alder
addition 114
3-tri-n-butylstannyl-, from 3-lithio- 101
cross coupling with thiophene-2-carbonyl chloride 102
in Stille reaction 25
2-ZnCl, in Negishi reaction 91
Furan-2(5H)-one, 5-hydroxy-, from furan-2-carboxylic acid 104
Furaneol 186
Furazan, 3,4-diamino-, see 3,4-Diamino-1,2,5-oxadiazole
Furfural, 5-hydroxy- 187
mechanism of formation from glucose 188
Furfuryl mercaptan, in coffee aroma 186
Fürstner synthesis of indoles 96
G, see Guanine
G.R.A.S., see Generally Regarded As Safe
GABA receptors 183
GABA, see -Aminobutyric acid
Gastric acid 170
Gastrozepin 171
Gemcitabine (Gemzar) 178
Gemzar 178
‘Generally regarded as safe’ (G.R.A.S.) 192
Glaucoma 171
-D-Glucopyranose 154
-D-Glucopyranose 154
Glucose 154
reaction with acetone 154
Glycerol, in Skraup synthesis of quinolines 68
Glycine 169
Glyoxal bis-imine, in ring synthesis of an N-heterocyclic
carbene 118, 119
Gout 124
Gramine, displacement of dimethylamine with
acetamidomalonate 93
from indole 88
Granisetron (Kytril) 172
Grapefruit juice 175
Grignard reagents, formation using i-PrMgCl 17, 53
Guanidine 56, 57
N-acetyl-, in ring synthesis of imidazoles 117
basicity 116
in ring synthesis of a 2-aminopyrimidine 58
Guanidinium cation 116
Guanine (G) 122, 123, 164
Guanosine 122, 123
Guareschi synthesis of pyridones 45, 46
Halogen donors 15
Halogenation 13
Halo-imine, nucleophilic substitution 14
-Halo ketones
in ring synthesis of furans 105
of imidazoles 116, 117
of thiazoles 116, 117
Halo-oximes, in formation of nitrile oxides 120
Hammick reaction 41
Hantzsch pyridine ring synthesis 45, 160
Heartburn 170
Heck reaction
examples 22, 26, 30
mechanism 29
Helminths 175
Heme 82, 162, 163
Hemlock 165
2,4,6-Heptatrienals, from pyrylium 72
1,3,4,5,7,9,9b-Heptazaphenalene 149
(Z)-Hept-3-ene-2,5-dione, from 2-ethyl-5-methylfuran 103
Heterocyclic ring syntheses
of 1-azabicyclo[1.1.0]butane 155
of azetidines 155, 157
of aziridines 155, 156
of 1-benzopyryliums 76
of benzotriazoles 140
of benzo[1,2-b:4,3-b]dipyrroles 85
of cinnnolines 61
of coumarins 191
of diketopiperazines 60
of fl avones 77
of furans 105, 114
of imidazoles 116, 117, 118, 119
of imidazo[2,1-b]oxazoles 148
of imidazo[1,2-a]pyridines 117, 147
of indoles 94, 95, 96, 97,
of indolizines 147
of isatins 97
of isoquinolines 69, 70
of isothiazoles 121
of isoxazoles 20, 120
of münchnones 116
of 1,2,5-oxadiazoles 139
of 1,6-naphthyridines 70
of 2,7-naphthyridines 70
of oxazoles 117, 118, 120
of oxetanes 155
of oxindoles 97
of oxiranes 155, 156
of phthalazinones 60
of piperidines 157
of pteridines 59
of purines 130, 131
of pyrazines 58, 59, 60
of pyrazoles 119, 120, 121, 183
of pyrazolo[1,5-a]pyridine 147
of pyrazolo[1,5-b]pyridazine 147
of pyridazines 58, 141
of pyridines 44, 45, 46, 54, 55, 115, 141, 157, 160
of pyrimidines 58, 59, 141
of 2-pyrones 76
of 4-pyrones 75
of pyrroles 83, 84, 157
of pyrrolidines 155, 156, 157
of pyryliums 74, 75
of quinazolines 45, 61, 148
of quinolines 68, 69
of quinoxaline 60
of saturated heterocycles 155–157
of 1,2,3,4-tetrahydrocarbazole 94