202 Index
Indoles (continued )
3-boronic acid-1-phenylsulfonyl-, from 3-lithio- 91
3-boronic acid-1-p-toluenesulfonyl-, in Suzuki–Miyaura
reaction 91
bromination 87
2-boronic acid, 1-t-butoxycarbonyl-, reaction with KHF 2 92
4-bromo-, ring synthesis 95
7-bromo-, ring synthesis 96
3-bromo-1-tri-isopropylsilyl-, from 3-lithio- 91
1-t-butoxycarbonyl-, preparation from indole 89
N-carboxylic acid lithium salt, 2-lithiation 90
cross-coupling at N with PhCH=CHBr 27
4,6-dibromo-2-ethyl-3-methyl-, ring synthesis 95
2,3-dihydro-, from reduction of indole 92
4,7-dihydro-, from Birch reduction of indole 92
1,3-dimethyl-, palladation at C-2 30
dipolar cycloaddition across C-2–C-3 92
disconnections for ring synthesis 94
electrophilic substitution
regioselectivity 86
mechanism and intermediates 89
7-ethyl-3-methyl-, ring synthesis 96
3-formyl-, from indole 88
2-n-hexyl-5-nitro-, ring synthesis 96
3-(2-hydroxyethyl), 1-phenylsulfonyl-, from 3-lithio- 91
2-iodo-, from indole 90
3-lithio-1-phenylsulfonyl-, from 3-bromo- 91
3-lithio-1-t-butyldimethylsilyl-, from 3-bromo- 91
3-lithio-1-tri-isopropylsilyl-, from 1-tri-
isopropylsilylindole 91
Mannich substitution 88
mesomeric/resonance structures 8
1-methyl-, reaction with BtCH 2 OH 137
1-methyl-3-benzotriazol-1-ylmethyl-, from
1-methylindole 137
3-nitro-1-phenylsulfonyl-, Diels–Alder reaction 93
dipolar cycloaddition with azomethine ylide 93
numbering 2
perfume component 191
pericyclic reactions 92, 93
2-phenyl-, ring synthesis 96
1-phenylsulfonyl-, nitration 88
from indole 89
1-phenylsulfonyl-2-trifl oxy-, in Suzuki–Miyaura reaction 27
2-propenyl-, Diels–Alder reaction 93
reaction with conjugated aldehydes, chiral catalyst 88
with conjugated ketones 88
with nitroethene 87
with oxalyl chloride 87
structure 8
sulfenylation 87
sulfonation 87
4,5,6,7-tetrahydro-, from Birch reduction of indole 92
2-trifl oxy-1-ethoxycarbonyl-, from
1-ethoxycarbonyloxindole 91
in Negishi reaction 91
1-tri-isopropylsilyl-, bromination 88
3-trifl uoroacetyl-, reaction with piperidine anion 87
3-trimethylstannyl-1-t-butyldimethylsilyl-, from
3-lithio- 91
5-trifl oxy-, in Negishi reaction 27
trifl uoroacetylation 87
2-trifl uoroborate, 1-t-butoxycarbonyl-, cross-coupling with
3-bromopyridine 92
Vilsmeier reaction 88
2-ZnCl, 1-t-butyldimethylsilyl-, from 2-bromo- 92
in Negishi reaction 92
Indolenium cation 86
Indoline, see 2,3-Dihydroindole
Indolium cation 86
Indolizine 143
acetylation 144
basicity 144
5-lithio-2-phenyl-, from 2-phenyl- 144
2-methyl-, nitration 144
pericyclic reaction 144
1-phenyl-, ring synthesis 147
protonation 144
reduction 144
5-trimethylsilyl-2-phenyl-, from 5-lithio- 144
Indolyl anion, formation with NaH 89
reaction with (t-BuOCO) 2 O 89
with 1-acylbenzotriazoles 89
with iodomethane 89
with PhSO 2 Cl 89
Indomethacin (Indocin) 174
Indoramin (Baratol) 173
Indoxyl
tautomerism 94
1-ethyl-, from 3-acetoxyindole 97
Initiation step, formation of palladium(0) 22
Inks 181
Inosine, see Hypoxanthine
Insomnia 173
Inverse-electron-demand Diels–Alder 19
Invirase 177
IPr, see 1,3-Bis(2,6-diisopropylphenyl)-1,3-dihydro-
2 H-imidazol-2-ylidene
i-Propylmagnesium chloride, use in forming Grignard
reagents 17, 53
Ipso electrophilic substitution, of hydrogen 10
Ipso electrophilic substitution, of silicon 10, 11
Irinotecan (Camptosar) 178
Isatin 94
7-(thien-3-yl)-, in ring synthesis of a quinoline 69
7-iodo-, in Suzuki–Miyaura reaction 102
ring synthesis from aniline 97
Isobenzofuran, numbering 2
Isochromylium 71
Isocoumarin 73
Isoindole, numbering 2
Isomaltol 187
mechanism of formation from
glucose 188
Isoniazid (Laniazid) 176
Isonicotinic acid 41
Isoquinolines
2-acetoxy-, from N-oxide 67
amination 64
2-amino-, from isoquinoline 64
basicity 62
bromination at C-4 63
2-bromo-, in Stille reaction 66
2-chloro-, from 2-isoquinolinone 67