Index 2094-iodo-2-methoxy-, cross-coupling with
n-Bu 3 SnSnn-Bu 3 54
4-iodo-2-methylthio-, formation of Grignard 53
4-lithio-, from the heterocycle 52
2-methanesulfonyl-, reaction with azide anion 51
2-oxy-, tautomerism 48
4-oxy-, tautomerism 48
2-thione, 4,6-dimethyl-, ring synthesis 59
5-tri-n-butylstannyl-2-methylthio-, in Stille reaction 25
4-tri-n-butylstannyl-2-methoxy, in Stille reaction 54
2-trimethylammonium-, reaction with cyanide anion 51
2-trimethylstannyl-6-methoxy, in Stille reaction 54
5-ethoxycarbonyl-, Diels–Alder with an alkyne 54
5-lithio-, from 5-bromo- 53
5-lithio-2,4-dimethoxy-, from 2,4-dimethoxy- 52
5-phenyl-, radical substitution 15
mesomeric/resonance structures 6
N-oxidation 49
numbering 2
reaction with hydrazine 50
structure 6
2,4,6-trione, 5-allyl-, conversion into trichloride 56
2,4,5,6-tetramino-, in ring synthesis of purines 130
2,4,5-triamino-, in ring synthesis of purines 130
2,4,6-trichloro-, reaction with an amide anion 51
Pyrimidine-2,4-dione, see Uracil
Pyrimidinium iodide, 2-amino-1-methyl-, conversion into
2-methylaminopyrimidine 57
2-Pyrimidinone, 4-amino-, Mannich substitution 50
N-arylation 56
4-Pyrimidinone, 2-ethoxy-, conversion to thione 56
2,6-diamino-5-hydroxy-, see Divicine
6-amino-2-methyl-, ring synthesis 59
6-hydroxy-, ring synthesis 59
2-Pyrone 73
bromination 73
5-bromo-, cross-coupling with pinacol borane 24
5-bromo-3-trimethylsilylethynyl-, Diels–Alder 74
a 5-boronate, in Suzuki–Miyaura reaction 24
5-carboxylic acid, see Coumalic acid
3,5-dibromo-, in Sonogashira reaction 74
Diels–Alder 74
nitration 73
reaction with ammonia 74
4-Pyrone
2,6-di(ethoxycarbonyl), see Chelidonic acid
from chelidonic acid 75
reaction with aniline 74
Pyrraline 190
Pyrrole
3-acetyl-4-methyl-, ring synthesis 84
acidity 7, 10
acylation 79
N-arylation 80
2-boronic acid-1-phenylsulfonyl-, from lithio
compound 80
3-boronic acid-1-tri-isopropylsilyl-, in Suzuki–Miyaura
reaction 23, 81
3-bromo-4-iodo-1-tri-isopropylsilyl-, in Suzuki–Miyaura
reaction 81
3-bromo-2-nitro-5-ethoxycarbonyl-, in Suzuki–Miyaura
reaction 66
1-t-butoxycarbonyl-, bromination 79
Diels–Alder 82
from pyrrole 80
3-carboxaldehyde, from N-silyl 81
3-carboxaldehyde-1-tri-isopropylsilyl-, from 3-lithio- 81
2-carboxylic acid-3,4-dimethyl-, decarboxylation 82
2,5-dihydro-1-phenylsulfonyl-, from
1-phenylsulfonylpyrrole 81
2,5-dihydro-N-Boc-, ring synthesis by metathesis 157
2-dimethylaminomethyl-, from pyrrole 79
reaction with cyanide 82
disconnections for ring synthesis 83
electrophilic substitution
intermediates 11
regiochemistry 78
3-ethoxycarbonyl-2,4-dimethyl-, ring synthesis 84
3-ethoxycarbonyl-5-t-butyl-2,4-dimethyl-, ring
synthesis 84
3-formyl-, from pyrrole 79
iodination 78
3-iodo-1-phenylsulfonyl-, in Sonogashira reaction 26
2-lithio-1-phenylsulfonyl-, from 1-phenylsulfonyl- 80
5-lithio-1-t-butoxycarbonyl-3-n-hexyl-, from the
heterocycle 80
3-lithio-1-phenylsulfonyl-, from bromide 81
Mannich substitution 79
mesomeric/resonance structures 7
nitration 78
numbering 2
1-phenyl-, ring synthesis 83
1-phenylsulfonyl-, bromination 79
reduction 81
polarization 7
reaction with acetone 83
with conjugated ketones 79
reduction 81
resonance energy 7
structure 7
2-tri-n-butylstannyl-1-t-butoxycarbonyl-, in Stille
reaction 81
2-trichloroacetyl-, nitration 80
trichloroacetylation 79
1-(tri-isopropylsilyl)- 78
bromination 79
from pyrrole 80
nitration 79
2-trimethylstannyl-5-bromo-, from 2-lithio 81
5-trimethylstannyl, 1-t-butoxycarbonyl-3-n-hexyl-, from
5-lithio- 80
Vilsmeier reaction 79
Pyrrolidines 3, 150
acidity 10
basicity 10, 153
from pyrrole 81
ring synthesis from N-chloro-amines 155
3 H-Pyrrolizine, see Pyrrolizine
Pyrrolizine 143
Pyrrolo[1,2-a]pyrazine 143, 145
Pyrrolo[1,2-c]pyridine, ring synthesis 147
Pyrrolo[2,1-b]thiazole 143
Pyrrolo[2,3-b]pyridine, see 7-Azaindole
Pyrrolo[2,3-c]pyridine, see 6-Azaindole