Index 207formation from pyrimidine 50
3-hydroxy-, tautomerism 115
iodination 110
2-lithio-1-pyrrolidinomethyl-, from the pyrazole 112
4-lithio-1-trityl-, from 4-bromo- 112
1-methyl-, reaction with iodomethane 108
3-methyl-5-trimethylsilylethynyl-, ring synthesis 120
nitration 109
4(5)-nitro-, tautomerism 109
numbering 2
reaction with an oxetan-2-one 153
2-tri-n-butylstannyl-1-methyl-, in Stille reaction 113
3-tri-n-butylstannyl-5-ethoxycarbonyl-, ring
synthesis 121
4-tri-n-butylstannyl-1-trityl-, from 4-lithio- 112
types of ring nitrogen 8
Pyrazolium cation 107
2-methyl-, side-chain deprotonation 108
Pyrazolo[1,5-a]pyridine 145
3-ethoxycarbonyl-, ring synthesis 147
Pyrazolo[1,5-b]pyridazine, 3-ethoxycarbonyl-, ring
synthesis 147
Pyrazolyl anion, from pyrazole 110
3-phenyl-, reaction with ethyl bromoacetate 111
Pyrethroids 182
Pyridazines
amination (Chichibabin) 14, 50
basicity 10, 48
4-boronic acid pinacol ester, in Suzuki–Miyaura reaction 53
a 6-chloro-3-amino-, intramolecular Diels–Alder
reaction 54
3,6-diiodo-, reaction with dimethylamine 51
nucleophilic substitution 14
3,6-dimethoxy-3-ZnCl, cross-coupling with
5-bromopyrimidine 54
4-dimethylamino-6-phenyl, from a cycloaddition 20
3,6-diphenyl-, ring synthesis 58
electrophilic addition to N 49
3-hydroxymethyl-, ring synthesis 58
4-iodo-3,6-dimethoxy-, formation of Grignard 53
3-lithio-, from the heterocycle 52
5-lithio-, from 4-t-butoxycarbonylamino- 52
4-methoxy-3,6-bis(methoxycarbonyl)-, ring synthesis 141
numbering 2
N-oxide, 3-nitro-, reaction with methoxide 57
4-nitro-, reaction with methoxide 57
nitration 50
reaction with NH 2 OSO 3 H 147
3-Pyridazinone
N-alkylation 55
6-hydroxy- 55
conversion into 3,6-dichloropyridazine 56
6-methyl-, ring synthesis 58
Pyridines
2-acetoxy-4-methoxy-, from N-oxide 42
2-acetoxymethyl-3-methyl-, from N-oxide 42
a 2-acetyl, via a Heck reaction 26
3-acetyl-2,4,6-trimethyl-, ring synthesis 46
3-acetyl, condensation at methyl 18
conversion into 2,2:6,2 -terpyridine 44
alkyl groups, acidity 40
C-amination 35
N-amination 33
2-amino-, bromination 35
reaction with 3-bromobutan-2-one 147
4-amino-, diazotisation 43
basicity 43
basicity 10
2,4-bis(trimethylstannyl)-, in Stille reaction 39
2-boronic acid, N-phenylethanolamine ester, in
Suzuki–Miyaura reaction 39
3-boronic acid, from 3-lithio- 38
Suzuki–Miyaura reaction 39
4-boronic acid-3-fl uoro-, from 4-lithio- 38
bromination 34
2-bromo-, cross-coupling with carbanion 26
in Negishi reaction 25, 92
3-bromo-, cross-coupling with n-Bu 3 SnSPh 27
cross-coupling with N-methylaniline 27
in Hiyama–Denmark reaction 25
in Stille reaction 25, 39
in Suzuki–Miyaura reaction 23, 24, 92
4-carboxylic acid, 2,3-dimethyl-, ring synthesis via
Diels–Alder reaction 115
2-chloro-, reaction with methoxide 36
from N-oxide 42
from 2-pyridone 41
2-chloro-4-ethoxycarbonyl-, in Kumada–Corriu
reaction 39
4-chloro-, lithiation at C-3 38
2-cyano, reaction with hydrazine 142
5-cyano-2-iodo-, Grignard reagent 38
2-deprotonation with BuLi–LiDMAE 38
3,5-diacetyl-1,4-dihydro-4-methyl-, ring synthesis 45
4-diazo-, reaction with H 2 O 43
2,5-dibromo-, cross-coupling with N,N-diBoc-hydrazine 27
in Suzuki–Miyaura reaction 31
reaction with a carbanion 36
3,4-dibromo-, reaction with ammonia 36
3,5-dibromo-, in Sonogashira reaction 39
2,3-dichloro-, conversion into 3-chloro-2-iodopyridine 37
cross-coupling with 3-diethylborylpyridine 31
reaction with Me 3 SiI 37
1,2-dihydro-1-alkoxy/aryloxycarbonyl- 36, 37
1,4-dihydro- 160
1,4-dihydro-1-t-butoxycarbonyl-3,5-di(thien-2-yl)-, from
cross-coupling 102
1,4-dihydro-1-t-butyldimethylsilyl, aromatization 37
1,4-dihydro-1-diethylaminocarbonyl, 3-acylation 37
1,4-dihydro-1-hydroxy-, intermediates in ring synthesis 44
4-diethylamino-3-ethoxycarbonyl-5-methyl-, ring
synthesis 54
4-dimethylamino- (DMAP), as nucleophilic catalyst
43, 192
dipole moment 5
disconnections for ring synthesis 43
electrophilic addition to N 33
electrophilic substitution 34
intermediates 12
regioselectivity 34
2-ethoxycarbonylmethyl-, reaction with ethoxymethylene
malonate 148
4-ethyl-2,6-dimethyl-4-ethoxycarbonyl-, ring synthesis 46
3-ethyl-4-n-propyl-, from Diels–Alder reaction 141