210 Index
Pyrrolo[3,2-b]pyridine, see 4-Azaindole
Pyrrolo[3,2-c]pyridine, see 5-Azaindole
Pyrryl anion, structure 7, 80
Pyruvate decarboxylase 161
Pyrylium cations
2,6-dimethyl-, ring synthesis 75
4-methyl-, reaction with NH 3 72
numbering 2
nucleophilic addition 71
perchlorate, ring synthesis 75
reaction with CH 2 =PPh 3 72
with n-BuLi 72
structure 5
2,4,6-trimethyl-, reaction with hydroxide 72
reduction 72
2,4,6-triphenyl-, ring synthesis 75
Pyrylium-3-olates, dipolar cycloaddition 73
preparation 73
Quercetin 166
Quercetrin 166
Quercitron bark 166
Quercus velutina 166
Quetiapine (Seroquel) 167
Quinazoline 48
Quinazoline, numbering 2
nitration 148
ring synthesis 148
Quinine 165, 175, 176
Quinolines
2-amino-3-cyano-5,6,7,8-tetrahydro-, ring synthesis 45
basicity 10, 62
4-boronic acid, in Suzuki-Miyaura reaction 66
3-bromo-, cross-coupling with bis(pinacolato)diboron 24
in Heck reaction 26
4-bromo-2-methyl-, from 2-methylquinolin-4-
one 67
2-chloro-, reaction with ethoxide 64
3-chloro-5,6,7,8-tetrahydro-5-oxo-, ring synthesis 46
2-cyano, from quinoline 64
disconnections for ring synthesis 67
hydrochloride 62
8-hydroxy- 194
3-lithio-2-chloro-, from 2-chloro- 64
mesomeric/resonance structures 6
2-methyl-, side-chain condensation with (CO 2 Et) 2 66
with PhCHO 66
2-methyl-3-phenyl-, ring synthesis 68
4-methyl, radical substitution 15
numbering 2
N-oxide 62
polarization 6
reaction with KOH–NaOH 64
with peracid 62
with TsCl/KCN 64
reduction 66
ring synthesis from aniline 68
structure 6
2-tri-n-butylstanyl-, in Stille reaction 66
Quinoline-4-carboxylic acid, 2-(4-chlorophenyl)methyl-
3-hydroxy-8-(thien-3-yl)-, ring synthesis 69
4 H-Quinolizine, see Quinolizine
Quinolizine 143
Quinolizinium 143
reaction with phenyl Grignard 147
ring synthesis 148
4-Quinolizinone 143
2-Quinolone, from quinoline 64
4-Quinolone, nitration at C-6, C-3 63
2-methyl-, reaction with PBr 5 67
4-Quinolone, 6-chloro-3-iodo-2-methyl-, in Suzuki–Miyaura
reaction 39
Quinoxaline 48
numbering 2
oxidation 60
ring synthesis 60Ramburg–Bäcklund reaction 152
Ranitidine (Zantac) 170
RDX 185
Reactive blue 4 181
Receptors, muscarinic/nicotinic 171
Reductive elimination in palladium(0) catalysis 28–29
Reissert compounds 65
Replication of DNA 164
Requip 174
Rescriptor 177
Resonance contributors 4
Resonance energy 4
Resonance hybrid 4
Resorcinol, in ring synthesis of a 1-benzopyrylium 76
of a coumarin 76
Retrovirus 163
Reverse transcription 163
Ribavirin (Copegus) 177
Ribofl avin, see Vitamin B 2
Ribose 122
Ribosomal RNA 163
Rilutek 174
Riluzole (Rilutek) 174
Ring fusion, nomenclature 1
Ring syntheses, see Heterocyclic ring syntheses
Risperdal 174
Risperidone (Risperdal) 174
RNA 48, 122, 163, 164
Rogaine 173
Ropinirole (Requip) 174
Rosuvastatin (Crestor) 167, 175
rRNA, see ribosomal RNASalicylaldehyde, in ring synthesis of a 1-benzopyrylium 76
of a coumarin 76
Saquinavir (Invirase) 172, 177
Sarin 172
Saturated sulfur rings, from 1, -dihalides with sulfi de 155
Scheele, Carl Wilhelm 75, 124
Schizophrenia 174
Second messenger 123
Selectfl uorTM 13
Semtex 185
Septrin 176
Seroquel 167
Serotonin 158, 169, 172
Sharpless synthesis of chiral oxiranes 156