Index 2031-cyano-, from N-oxide 67
1,3-dichloro-, reaction with methoxide 64
selectivity in Pd(0)-cross-coupling 65, 66
3,4-dihydro-6-methoxy-1-phenyl-, ring
synthesis 69
disconnections for ring synthesis 67
electrophilic substitution, regiochemistry 62
4-lithio-, from 4-bromo- 64
7-methoxy-, ring synthesis 69
6-methoxy-1-phenyl-, from 3,4-dihydro- 69
nitration at C-5/C-8/C-4 63
nucleophilic substitution, regiochemistry 63
numbering 2
N-oxide, reaction with Ac 2 O 67
reaction with Me 3 SiCN 67
1-phenyl-, from 1-phenyl-2-benzopyrylium 72
polarisation 6
reaction with iodomethane 62
with n-BuLi 64
with PhCOCl/KCN 65
structure 6
Isoquinolinium iodide
2-methyl-, from isoquinoline 62
reduction 66
oxidation to 1-isoquinolone 66
Isoquinolinium, 2-(2,4-dinitrophenyl)-, see Zincke’s salt
1-Isoquinolone, reaction with POCl 3 67
2-methyl-, from 2-methylisoquinolinium iodide 66
Isosteric replacement 132, 133
Isothiazoles
basicity 10, 107
3,5-dichloro-4-cyano-, reaction with ammonia 110
disconnections for ring synthesis 119
5-hydroxy, tautomerism 115
4-iodo-, formation of Grignard 112
5-lithio-, from isothiazole 112
nitration 109
numbering 2
5-tosylamino-4-ethoxycarbonyl-3-methyl-,
ring synthesis 121
5-Isothiazolone, tautomerism 115
Isothiazolium, 3-methyl-, perchlorate 107
Isoxazoles
basicity 10, 107
disconnections for ring synthesis 119
4-iodo-3,5-dimethyl-, in Suzuki–Miyaura reaction 24
4-methoxycarbonyl-3-phenyl-, ring synthesis 120
nitration 109
numbering 2
ring opening with base 112
ring synthesis by nitrile oxide cycloadditions 20
2-Isoxazolidinone, 5-methyl-, side-chain lithiation 114
N–O reductive cleavage 114
Italic ‘H’, use in nomenclature 1
Jasmine 191
KDNBF 186
-Keto acid, from -amino acid 161
1,3-Keto-aldehydes, synthetic equivalents 18, 44
Ketorolac (Acular) 174
Kirkpatrickia variolosa 166
Knorr synthesis of pyrroles 83, 84
Kumada–Corriu reaction, examples 25, 39
Kytril 172-Lactone 153
Lamellaria sp. 166
Lamellarin B 166
Lamictal 174
Lamivudine 177
Lamotrigine (Lamictal) 174
Laniazid 176
Largactil 174
-Lactams 153
from imines 157
from isocyanates 157
via cycloaddition of azomethine ylides 157
Lariam 176
Lawesson’s reagent 105
LDA, see Lithium diisopropylamide
‘Lead compound’ 169
Lead azide 186
Lead styphnate 186
Leaving groups in cross-couplings, selectivity 31
Leimgruber–Batcho synthesis of indoles 95
Lepidoptera 159
Leukotriene antagonists 170
Levistamel 191
Levulinic acid, 5-amino-, see 5-Aminolevulinic acid
Lipitor 167
Lithium diisopropylamide (LDA), use to form organolithium
reagents 16
LLM-105 185
L-Lysine 189
Loratidine (Clarityn) 170
Losarten 133
Losec 171
Luminal 174M5 fi bre 182
Maillard reaction 187–189
Malarone 176
Malealdehydic acid 104
Maleic hydrazide 55
Malic acid, decarbonylation 59, 75, 76
Malondialdehyde, synthetic equivalents 46, 120
Maltol 187
mechanism of formation from glucose 188
Manganese(IV) oxide, in dehydrogenation, giving
thiazoles 118
Mannich reaction, mechanism 12
Maple syrup aroma 186
Mauve 180
Mauveine, see Mauve
McMuray coupling 96
Mebendazole (Vermox) 176
Medicines, nomenclature 167
Mefl oquine (Lariam) 176
Melamine 139
Melamine-formaldehyde polymers 181
Melatonin 158
6-Mercaptopurine (Purinethol) 178
Mesomeric structures 4