《CHEMISTRY OF CARBON COMPOUNDS VOLUME IV PART B HETEROCYCLIC COMPOUNDS》求取 ⇩

Chapter Ⅷ．Compounds Containing a Six-Membered Ring with One Hetero A tom,Oxygen or Sulphur＆by NEIL CAMPBELL809

Introduction809

1．Pyran and its Derivatives810

a．Pyrans,Pyranols and Pyrones810

(ⅰ)α-and γ-Pyrans810

(ⅱ)Pyranols811

(ⅲ)Pyrylium Salts811

(ⅳ)α-and γ-Pyrones814

α-Pyrones815

Methods of Preparation815

Properties817

γ-Pyrones821

Constitution and Fine Structure821

Methods of Preparation822

Properties823

(ⅴ)Hydroxy-γ-pyrones828

(ⅵ)γ-Pyronecarboxylic Acids832

b．Dihydropyrans and their Oxidation Products835

(ⅰ)2:3-Dihydro-γ-pyran835

(ⅱ)5:6-Dihydro-α-pyran837

(ⅲ)Naturally Occurring Furodihydropyran Derivatives837

c．Tetrahydropyran and Derivatives839

2．5:6-Benzopyrans(Chromens)and their Derivatives841

a．Chromens and their Oxidation Products842

(ⅰ)Chromens,Alkyl-and Aryl-chromens842

(ⅱ)Chromenols(5:6-Benzopyranols)846

(ⅱa)Benzopyrylium or Chromylium Salts847

Methods of Synthesis847

Fine Structure of the Benzopyrylium Salts850

Properties850

(ⅱb)The Anthocyanins and Anthocyanidins855

Methods of Synthesis859

(ⅱc)Leucoanthocyanins867

(ⅲ)Cou-marin(5:6-Benzo-α-pyrone)and its Derivatives869

Synthesis869

Properties872

(ⅲa)Coumarin,Alkyl-and Aryl-coumarins875

(ⅲb)Hydroxycoumarins878

(ⅲc)Naturally Occurring Coumarin Deriva-tives880

(1)Naturally Occurring Hydroxycoumarins881

(2)Furo-coumarins883

(3)Coumarins Containing a Fused 2:2-Dimethyl-chromen Nucleus887

(ⅳ)Chromones(5:6-Benzo-γ-pyrones)888

Methods of Synthesis889

Structure and Properties893

(ⅳa)Chro-mone,Alkylchromones and Hydroxychromones897

(ⅳb)Naturally Occurring Chromones898

(1)Hydroxychromones898

(2)Furochro-mones900

(3)Pyranochromones902

(ⅳc)Flavones(2-Phenylchro-mones)903

(ⅳd)Flavonols(3-Hydroxyflavones)906

(ⅳe)Flavone and Flavonol Pigments907

Synthesis908

Hydroxyflavones with no 3-Hydroxyl Group910

Hydroxyflavones with a 3-Hydroxyl Group;Hydroxyflavonols914

Furoflavones920

(ⅳf)isoFlavones(3-Phenyl-chromones)921

Naturally Occurring isoFlavones924

b．Chroman(Dihydrochromen)and Derivatives927

(ⅰ)Chromans927

(ⅱ)Naturally Occurring Chromans928

Tocopherols928

Structure929

Properties931

(ⅲ)Phenylchromans(Flavan and isoFlavan)932

(ⅳ)Chromanols934

(ⅴ)Flavanols:the Catechins and Related Condensed Tannins935

Catechins935

Condensed Tan-nins940

(ⅵ)Chromanones942

Chromanochromanones．Rotenone and Related Substances944

(ⅶ)Flavanones,2-Phenylchroman-4-ones954

(ⅷ)Hydroxyflavanones956

(ⅸ)isoFlavanones,3-Phenyl-chroman-4-ones961

3．isoBenzopyran(3:4-Benzopyran)and its Derivatives961

a．isoCoumarins962

b．isoChroman and Derivatives965

4．Xanthen(2:3-5:6-Dibenzopyran)and its Derivatives966

a．Xanthen,Alkyl-and Aryl-xanthens966

b．Xanthhydrols and Xanthen Colouring Matters969

(ⅰ)Fluorones and Fluorimes970

(ⅱ)Xanthen Dyes971

(1)Pyronines972

(2)Rosamines and Rhodamines973

(3)Fluorescein and Related Compounds974

c．Xanthones976

Methods of Synthesis976

(ⅰ)Halogenoxanthones978

(ⅱ)Nitro-and Amino-xanthones979

(ⅲ)Hydroxyxanthones980

5．3:4-Benzochromen and its Derivatives983

6．5:6-Benzochromens and their Derivatives984

7．6:7-Benzochromens and their Derivatives985

8．7:8-Benzochromens and their Derivatives986

9．Benzo-and Dibenzo-xanthen Derivatives987

10．Thiapyran Derivatives988

a．Thiapyrans and Thiapyrones988

b．Hydrogenated Thiapyrans and Thiapyrones989

(ⅰ)Dihydrothiapyrans989

(ⅱ)Tetrahydrothiapyrans990

11．Thiachromens(5:6-Benzothiapyrans)and Derivatives992

a．5:6-Benzothiapyrans and 5:6-Benzothiapyrones992

(ⅰ)Thiachromens992

(ⅱ)Thiacoumarins993

(ⅲ)1-Thiachromones and 1-Thiaflavones993

b．Thiaehromans and Thiachromanones994

12．Dibenzothiapyran(Thiaxanthen)and Derivatives997

13．isoThiachromen(3:4-Benzothiapyran)and Derivatives1001

a．isoThiachromen and isoThiacoumarins1001

b．isoThiachroman and Derivatives1001

14．Bridged Ring Sulphur Compounds1002

Chapter Ⅸ．Brazilin and Haematoxylin＆by Sir ROBERT ROBINSON1005

1．The Brazilin Group1005

Oxidation of O-Trimethylbrazilin by Means of Permanganate1007

Oxidation of O-Trimethylbrazilin by Means of Chromic Acid in Acetic Acid Solution1009

Brazilein and its Derivatives1013

The iso-Brazilein or Brazylium Salts1016

Synthesis of Brazylium and Other Indenobenzopyrylium Salts1017

Synthesis of Deoxytrimethylbrazi-lone and Trimethylbrazilone1018

The Constitution of Brazilein1019

Synthesis of Brazilin1020

2．The Haematoxylin Group1021

Permanganate Oxidation of d-Tetramethylhaematoxylin1021

Haematin and its Derivatives1022

Possible Natural Occurrence of a Haematoxylin Methyl Ether1023

Optical Rotatory Powers of Brazilin and Haematoxylin and their Derivatives1023

Chapter Ⅹ．Compounds Containing Two Fused Five-or Six-Mernbered Heterocyclic Rings Each of One Hetero Atom＆by NEIL CAMPBELL1024

1．Compounds Containing Two Hetero Rings Fused to an Aromatic System1024

a．Pyranoquinolines1024

b．Bz-Pyrroloquinolines1025

c．Phenanthrolines1026

d．Dipyridonaphthalenes1027

2．Compounds Containing Two Hetero Rings Fused Through Adjacent Carbon Atoms1028

a．Furanoquinolines1028

b．Pyranoquinolines1030

c．Pyrrolopyridines or Diazaindenes1031

Carbolines1033

Indoloquinolines or Quinindolines1034

d．Naphthyridines or Pyridopyridines1035

3．Fused Heterocyclic Systems Having a Nitrogen Atom Common to Two Rings1038

a．Pyrrocolines1038

b．Pyridocolines1041

Norlupinane and Lupinane1042

c．Julolidine and Lilolidine1046

4．Bridged Ring Compounds1048

a．Compounds with Nitrogen Common to Two Rings1048

b．Bicyclic Systems Having a Nitrogen Bridge1051

Chapter Ⅺ．The Cyanine and Related Dyes＆by G．DE W．ANDERSON1053

Introduction1053

1．Cyanines1054

Historical1054

Methods of Preparation1056

(ⅰ)Monomethincyani-nes1056

(ⅱ)Trimethincyanines1058

(ⅲ)Meso-substituted Unsym-metrical Trimethincyanines1060

(ⅳ)Symmetrical Trimethincyanines with Miscellaneous Chain Substituents1061

(ⅴ)Penta-and Higher Poly-methincyanines1062

Properties of the Cyanine Dyes1064

Typical Compounds1066

2．Azacyanines1068

3．Neocyanines and Related Dyes1069

4．Merocyanines1071

Methods of Preparation1072

Properties of the Merocyanine Dyes1074

Typical Compounds1075

5．Linear Tri-and Poly-nuclear Cyanines and Merocyanines1075

Properties1076

Typical Compounds1077

6．Oxonol Dyes1078

7．Styryl Dyes and N-Hemicyanines1079

Chapter Ⅻ．The Indigo Group＆by T．S．STEVENS1081

Introduction1081

1．Indigo(Indigotin)and its Derivatives1083

Constitution1083

Synthetic Methods1085

Properties1087

(ⅰ)N-Derivatives of Indigo1089

(ⅱ)Derivatives of the Carbonyl Function1091

(ⅲ)Homologues of Indigo1091

(ⅳ)Halogeno-indigos1092

(ⅴ)Other Substituted Indigos1092

(ⅵ)Dehydroindigo1093

(ⅶ)Indigo-white1094

(ⅷ)Polycyclic Indigos1094

2．Indirubin1095

3．isoIndigo1097

4．Other Indigoid Pigments1098

a．Thioindigos1098

b．Thionaphthenindoleindigos1102

c．Vinylene Homologues of the Indigos1103

Chapter ⅩⅢ．The Pyrrole Pigments＆by T．S．STEVENS1104

Introduction1104

1．Linear Pigments1105

a．Dipyrromethenes and Related Compounds1105

Methods of Synthesis1105

(ⅰ)Simple Dipyrromethenes1107

(ⅱ)Hydroxydipyrromethenes or their Tautomerides1109

(ⅲ)Tri-and Poly-nuclear Systems1110

b．Bile Pigments(Bilirubinoids)1111

Nomenclature1112

Synthetic Methods1114

(ⅰ)Bilitrienes1114

(ⅱ)Bilidienes1115

(ⅲ)Bilenes and Bilans1118

(ⅳ)Diagnostic Reactions1118

2．Macrocyclic Pigments:Unreduced Porphins1119

Synthetic Methods1120

General Properties1122

a．Porphin and its Simple Derivatives1124

b．Porphinpropionic Acids1126

c．Haemoglobin1128

(ⅰ)Structure of Protoporphyrin and Haemin1128

(ⅱ)Haemoglobin:Properties and Transformations1130

d．Other Porphyrin-Protein Complexes1131

e．Naturally Occurring Protein-free Porphyrins1133

3．Reduced Porphins．Chlorophyll1134

a．Synthetic Reduced Porphins1134

(ⅰ)Dihydroporphins1134

(ⅱ)Tetra-,Hexa-,and Octa-hydroporphins1138

b．Chlorophyll1139

Nomenclature1140

(ⅰ)Structure and Reactions of Chlorophyll-a1140

The Porphin Skeleton1140

The Homocyclic Ring1142

The Vinyl Group1143

The Phorbide-Porphyrin Relationship1143

The＂Extra＂Hydrogen Atoms:Location1144

Other Transformations of Chlorophyll-a1145

(ⅱ)Chlorophyll-b1146

(ⅲ)Absorption Spectra of Phorbides and Chlorins1147

(ⅳ)Bacteriochlorophyll1149

c．Biosynthesis of Porphyrins1149

d．Vitamin B12(Cyanocobalamine)1151

4．Aza-and Benzo-porphins;Phthalocyanines1154

a．Azaporphins1155

(ⅰ)Monoazaporphins1155

(ⅱ)Diazaporphins1155

(ⅲ)Tetraaza-porphins1156

b．Benzoporphins and Benzoazaporphins1156

Synthetic Methods1157

(ⅰ)Tetrabenzoporphin1158

(ⅱ)Tetrabenzo-mono-,-di-,and-tri-aza-porphins1158

(ⅲ)Tetrabenzotetraaza-porphins(Phthalocyanines)1159

(ⅳ)Macrocyclic Systems Related to Phthalocyanine1162

Chapter ⅩⅣ．Compounds Containing Unusual Hetero Aoms＆by(Miss)I．G．M．CAMPBELL and(in part)T．S．STEVENS1163

1．Five Membered Rings with One Hetero Atom1163

a．Silicon Compounds1163

b．Phosphorus Compounds1164

c．Arsenic Compounds1166

d．Antimony Compounds1168

e．Halogen Compounds1169

2．Five Membered Rings with more than One Hetero Atom1170

a．Five Membered Rings Containing Silicon and Oxygen or Sulphur1170

b．Five Membered Rings Containing Phosphorus and Oxygen or Nitrogen1170

c．Five Membered Rings Containing Arsenic and Oxygen1171

d．Five Membered Rings Containing Arsenic and Sulphur1173

e．Five Membered Rings Containing Antimony and Oxygen1174

f．Five Membered Rings Containing Antimony and Sulphur1174

g．Five Membered Rings Containing Bismuth and Oxygen or Sulphur1175

3．Six Membered Rings Having One Hetero Atom1176

a．Silicon Compounds1176

b．Germanium,Tin and Lead Compounds1177

c．Phosphorus Compounds1178

d．Arsenic Compounds1180

(ⅰ)Arsacyclohexanes1180

(ⅱ)Tetrahydroarsinolines1181

(ⅲ)Ars-acridines1183

(ⅳ)Arsaphenanthrenes1183

(ⅴ)Arsaperinaphth-indane1184

e．Antimony and Bismuth Compounds1184

f．Iodine Compounds1185

4．Six Membered Rings with more than One Hetero Atom1186

a．Six Membered Rings Containing Silicon with Oxygen,Sulphur or Nitrogen1186

b．Six Membered Rings Containing Phosphorus with Oxygen or Nitrogen1189

c．Six Membered Rings Containing Arsenic with Oxygen,Sulphur or Nitrogen1190

d．Six Membered Rings Containing Antimony and Oxygen1193

e．Six Membered Rings Containing Two Phosphorus Atoms or Phos-phorus and Arsenic1194

f．Six Membered Rings Containing Two Arsenic Atoms1195

5．Seven Membered and Larger Rings1197

a．Silicon and Tin Compounds1197

b．Phosphorus and Arsenic Compounds1198

c．Larger Rings Containing Two Arsenic Atoms1199

d．Iodine Compounds1200

Bibliography1200

Chapter ⅩⅤ．Compounds Containing a Six Membered Ring with Two Hetero Atoms．The Diazines＆by G．R．RAMAGE and(in part)J．K．LANDQUIST1201

1．The Pyridazine Group1201

a．Pyridazine and its Substitution Products1201

Methods of Synthesis1202

(ⅰ)Pyridazine and its Alkyl and Aryl Derivatives1204

(ⅱ)Halogenopyridazines1205

(ⅲ)Aminopyrida-zines1205

(ⅳ)Hydroxypyridazines(Pyridazones)1206

(ⅴ)Pyrida-zinecarboxylic Acids1209

b．Hydropyridazines1211

(ⅰ)Dihydropyridazines1211

(ⅱ)Tetrahydropyridazines1215

(ⅲ)Hexahydropyridazines(Piperidazines)1216

Benzopyridazines1217

c．Cinnoline and its Substitution Products1217

Methods of Synthesis1217

(ⅰ)Cinnoline and its Alkyl and Aryl Deri-vatives1218

(ⅱ)Reduced Cinnolines1220

(ⅲ)Halogenocinnolines1221

(ⅳ)Nitrocinnolines1222

(ⅴ)Aminocinnolines1223

(ⅵ)Hydroxycinnolines1228

(ⅶ)Cinnolinecarboxylic Acids1232

d．Benzo[c]cinnolines1233

(ⅰ)Benzo[c]cinnoline and its Alkyl Derivatives1234

(ⅱ)Halogeno-,Nitro-and Other Substituted Benzo[c]cinnolines1235

(ⅲ)Reduced Benzo[c]cinnolines1237

e．Other Benzocinnolines1237

f．Phthalazines1238

Methods of Synthesis1238

(ⅰ)Phthalazine,its Alkyl and Aryl Deri-vatives1239

(ⅱ)Reduced Phthalazines1240

(ⅲ)Halogenophthala-zines1241

(ⅳ)Aminophthalazines1242

(ⅴ)Hydroxyphthalazines and Dihydrophthalazines1244

(ⅵ)Phthalazine Compounds from Benzenediazonium Salts of 2-Naphthol-1-sulphonic acid1253

2．The Pyrimidine Group1257

a．Pyrimidine(1:3-Diazine)and its Substitution Products1257

Methods of Synthesis1257

Properties1260

(ⅰ)Pyrimidine,Alkyl-and Aryl-Pyrimidines1261

(ⅱ)Halogenopyrimidines1262

(ⅲ)Nitroso-and Nitro-Pyrimidines1264

(ⅳ)Aminopyrimidines1265

Monoaminopyrimidines1265

Di-and Poly-aminopyrimidines1269

(ⅴ)Hydroxypyrimidines1271

Monohydroxypyrimidines1271

Dihydroxypyrimidines1273

Hydrogenated Dihydroxypyrimidines1276

Trihydroxypyrimidines1276

Reactions of Barbituric Acid1278

Tetrahydroxypyrimidines1280

(ⅵ)Mercapto-and Alkylthio-Pyrimidines1281

(ⅶ)Aminohydroxypyrimidines1283

Monoamino-monohydroxypyrimidines1283

Diaminomonohydroxypyrimidines1285

Monoaminodihydroxypyrimidines1286

Diaminodihydroxy-pyrimidine1288

Monoaminohydroxypyrimidines1290

Triamino-monohydroxypyrimidines1291

(ⅷ)Pyrimidine Aldehydes1292

(ⅸ)Pyrimidinecarboxylic Acids1292

b．Hydrogenated Pyrimidines1295

Alloxan and Related Compounds1295

c．Quinazolines(Benzopyrimidines)1299

Methods of Synthesis1299

Properties and Reactions1301

(ⅰ)Quina-zoline and Homologues1305

(ⅱ)Chloroquinazolines1305

(ⅲ)Amino-quinazolines1306

(ⅳ)Hydroxyquinazolines(Quinazolones)and Mercap-toquinazolines1307

(ⅴ)Aldehydes and Ketones1311

(ⅵ)Carboxy-lic Acids1311

(ⅶ)Benzoquinazolines and Related Compounds1312

d．Hydrogenated Quinazolines1315

3．The Pyrazine Group1318

a．Pyrazines,1:4-Diazines1318

Methods of Synthesis1319

(ⅰ)Pyrazine,Alkyl-and Aryl-Pyrazines1320

(ⅱ)Halogenopyrazines1322

(ⅲ)Aminopyrazines1323

(ⅳ)Hydroxypyrazines1325

(ⅴ)Pyrazinecarboxylic Acids1329

Amino-and Hydroxy-pyrazinecarboxylic Acids1332

b．Hydropyrazines1333

(ⅰ)Dihydropyrazines1333

(ⅱ)Tetrahydropyrazines1336

(ⅲ)Pipera-zines(Hexahydropyrazines)1338

Methods of Synthesis1338

Stereo-chemistry of NN′-Disubstituted Piperazines1341

Piperazines with Sub-stituents on Carbon1342

Ketopiperazines(Oxopiperazines)1343

c．Quinoxalines(Benzopyrazines)1345

Methods of Synthesis1345

(ⅰ)Quinoxaline and its Alkyl and Aryl Derivatives1347

(ⅱ)Halogenated Quinoxalines1351

(ⅲ)Nitroquin-oxalines1353

(ⅳ)Aminoquinoxalines1353

(ⅴ)Hydroxyquinoxalines1355

2-Hydroxyquinoxalines1355

2:3-Dihydroxyquinoxalines1358

Bz-Hydroxyquinoxalines1360

(ⅵ)Quinoxaline-N-oxides1361

(ⅶ)2-Polyhydroxyalkylquinoxalines1362

(ⅷ)Quinoxaline-2-aldehydes1364

(ⅸ)Quinoxaline-2-carboxylic Acids1365

Quinoxaline-2:3-dicarboxylic Acids1367

d．Hydrogenated Quinoxalines1368

(ⅰ)1:2-Dihydroquinoxalines1368

(ⅱ)1:2:3:4-Tetrahydroquinoxalines1368

e．Phenazines(Dibenzopyrazines)1371

General Methods of Synthesis1372

(ⅰ)Phenazine and its Homologues1374

(ⅱ)Benzo-and Dibenzo-phenazines1376

(ⅲ)Halogenophena-zines1377

(ⅳ)Nitrophenazines and Phenazinesulphonic Acid1378

(ⅴ)Aminophenazines1380

(ⅵ)Hydroxyphenazines1381

Dihydroxy-phenazines1383

(ⅶ)Phenazinecarboxylic Acids1384

f．Hydrogenated Phenazines1385

(ⅰ)5:10-Dihydrophenazines1385

(ⅱ)1:2:3:4-Tetrahydrophenazines1387

(ⅲ)Oetahydrophenazines1388

(ⅳ)Dodecahydrophenazines1389

INDEX1391