Quinazolines, Volume 55, Supplement 1

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ISBN: 9780471145653 | 0471145653
Cover: Hardcover
Copyright: 12/24/1996

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This supplement reflects and emphasizes current research trends. Due to the vast increase in the number and types of individual quinazolines described in recent literature, the author has replaced the myriad classified tables of known quinazolines with a single alphabetical table of simple known quinazolines. To facilitate recovery of any earlier data from the tables in the original volume, a cross-reference has been added (when appropriate) to each individual entry in the new table. Contains an extensive chapter on primary syntheses.

CHAPTER 1. PRIMARY SYNTHESES

(150)

1.1 From a Single Benzene Substrate

(30)

1.1.1 By Formation of the 1,2-Bond

(4)

1.1.2 By Formation of the 1,8a-Bond

(1)

1.1.3 By Formation of the 2,3-Bond

(13)

1.1.3.1 From o-Acylaminobenzamides

(4)

1.1.3.2 From o-Acylaminobenzamide Oximes

(1)

1.1.3.3 From o-(Alkoxycarbonylamino)-benzamides

(1)

1.1.3.4 From o-Ureidobenzamides

(2)

1.1.3.5 From o-(Benzylideneamino)benzamides

(1)

1.1.3.6 From o-Acylaminobenzonitriles

(2)

1.1.3.7 From o-(Substituted Methyleneamino)benzonitriles

(1)

1.1.3.8 From o-(Acylamino)benzaldehyde Hydrazones and Related Substrates

(1)

1.1.3.9 From Miscellaneous Substrates

(1)

1.1.4 By Formation of the 3,4-Bond

(9)

1.1.4.1 From o-Ureidobenzoic Acids

(2)

1.1.4.2 From o-Ureidobenzoic Esters

(1)

1.1.4.3 From o-Ureidobenzoyl Chlorides or o-Ureidobenzamides

(1)

1.1.4.4 From o-Ureidobenzonitriles

(1)

1.1.4.5 From o-Ureidobenzaldehyde Derivatives and Related Substrates

(2)

1.1.4.6 From o-(Aminomethyleneamino)-benzoic Acids, Esters, or Amides

(1)

1.1.4.7 From Miscellaneous Substrates

(2)

1.1.5 By Formation of the 4,4a-Bond

(4)

1.2 From a Benzene Substrate and Ancillary Synthon(s)

(72)

1.2.1 Where the Synthon Supplies N1

(1)

1.2.2 Where the Synthon Supplies C2

(18)

1.2.2.1 The Use of Carboxylic Acids and Related Synthons

(13)

1.2.2.2 The Use of Carbonic Acid-Derived Synthons

(5)

1.2.3 Where the Synthon Supplies N3

(13)

1.2.3.1 With o-Acylaminobenzoic Acids as Substrates

(1)

1.2.3.2 With o-Acylaminobenzoic Esters as Substrates

(2)

1.2.3.3 With o-Acylaminobenzonitriles as Substrates

(1)

1.2.3.4 With o-Acylaminobenzaldehydes or Related Ketones as Substrates

(1)

1.2.3.5 With o-(Alkoxycarbonylamino)-benzoic Esters or Related Ketones as Substrates

(2)

1.2.3.6 With o-(Substituted Methyleneamino)benzoic Esters or Related Ketones as Substrates

(1)

1.2.3.7 With o-(Substituted Methyleneamino)benzonitriles as Substrates

(2)

1.2.3.8 With o-Isocyanatobenzoyl Chlorides as Substrates

(1)

1.2.3.9 With o-Isocyanatobenzoic Esters and Related Ketones or Nitriles as Substrates

(2)

1.2.3.10 With o-Cyanoamino-or o-Ureidobenzoic Esters and Related Ketones or Nitriles as Substrates

(1)

1.2.3.11 With Miscellaneous Substrates

(1)

1.2.4 Where the Synthon Supplies C4

(2)

1.2.5 Where the Synthon(s) Supply N1 + C2

(2)

1.2.6 Where the Synthon(s) Supply C2 + N3

(22)

1.2.6.1 With o-Aminobenzoic Acids as Substrates

(7)

1.2.6.2 With o-Aminobenzoic Esters as Substrates

(5)

1.2.6.3 With o-Aminobenzamides as Substrates

(2)

1.2.6.4 With o-Aminobenzonitriles as Substrates

(3)

1.2.6.5 With o-Aminobenzaldehydes or Related Ketones as Substrates

(4)

1.2.6.6 With Miscellaneous o-Disubstituted Benzenes as Substrates

(1)

1.2.7 Where the Synthon(s) Supply N3 + C4

(4)

1.2.7.1 With N-Acylanilines as Substrates

(2)

1.2.7.2 With N-(a-Chloromethylene)anilines or Related Compounds as Substrates

(1)

1.2.7.3 With Other Aniline Derivatives as Substrates

(1)

1.2.8 Where the Synthon(s)Supply N1 + C2 + N3

(5)

1.2.8.1 With o-Halogeno or o-Alkoxybenzonitriles as Substrates

(1)

1.2.8.2 With o-Substituted Benzoic Esters or Related Compounds as Substrates

(1)

1.2.8.3 With o-Substituted Acetophenones or Related Compounds as Substrates

(1)

1.2.8.4 With 2-Methylenecyclohexanones as Substrates

(1)

1.2.8.5 With Miscellaneous Substrates

(1)

1.2.9 Where the Synthon(s) Supply C2 + N3 + C4

(3)

1.2.10 Where the Synthon(s) Supply N1 + C2 + N3 + C4

100

(3)

1.3 From a Single Pyrimidine Substrate

103

(1)

1.4 From a Pyrimidine Substrate and Ancillary Synthon(s)

104

(3)

1.5 From a Heteromonocyclic Substrate Other than a Pyrimidine

107

(4)

1.5.1 Imidazoles as Substrates

108

(1)

1.5.2 1,3,5-Oxadiazines as Substrates

108

(1)

1.5.3 1,2,4-Oxadiazoles as Substrates

108

(1)

1.5.4 1,3,4-Oxadiazoles as Substrates

109

(1)

1.5.5 1,2,3,5-Oxathiadiazines as Substrates

109

(1)

1.5.6 Oxazoles as Substrates

110

(1)

1.5.7 1,2,4,5-Tetrazines as Substrates

110

(1)

1.5.8 1,2,3,4-Thiatriazoles as Substrates

111

(1)

1.6 From a Heterobicyclic Substrate

111

(26)

1.6.1 Benzazetines as Substrates

111

(1)

1.6.2 2,1-Benzisothiazoles as Substrates

112

(1)

1.6.3 2,1-Benzisoxazoles as Substrates

112

(1)

1.6.4 1,4-Benzodiazepines as Substrates

113

(3)

1.6.5 1,5-Benzodiazocines as Substrates

116

(1)

1.6.6 2,1,4-Benzothiadiazepines as Substrates

117

(1)

1.6.7 2,1,3-Benzothiadiazines as Substrates

117

(1)

1.6.8 1,3-and 3,1-Benzothiazines as Substrates

117

(3)

1.6.9 1,2,4-Benzotriazepines as Substrates

120

(1)

1.6.10 1,3,4-Benzotriazepines as Substrates

120

(1)

1.6.11 1,2,3-Benzotriazines as Substrates

121

(1)

1.6.12 4,1,5-Benzoxadiazocines as Substrates

122

(1)

1.6.13 3,2,1-Benzoxathiazines as Substrates

123

(1)

1.6.14 1,3-Benzoxazines as Substrates

123

(1)

1.6.15 3,1-Benzoxazines as Substrates

124

(8)

1.6.16 Cinnolines as Substrates

132

(1)

1.6.17 Indazoles as Substrates

133

(1)

1.6.18 Indoles as Substrates

134

(1)

1.6.19 Isoindoles as Substrates

135

(1)

1.6.20 Phthalazines as Substrates

136

(1)

1.6.21 Quinolines as Substrates

136

(1)

1.7 From a Heterotricyclic Substrate

137

(8)

1.7.1 Azirino [2,3-b]indoles as Substrates

137

(1)

1.7.2 Benzo[c]cinnolines as Substrates

137

(1)

1.7.3 5,8-Epoxyquinazolines as Substrates

138

(1)

1.7.4 Imidazo[1,2-c]quinazolines as Substrates

138

(1)

1.7.5 [1,2,4]Oxadiazolo[2,3-c]quinazolines as Substrates

139

(1)

1.7.6 [1,3]Oxazino-and Oxazolo[2,3-b]quinazolines as Substrates

139

(1)

1.7.7 Pyrazolo[1,5-c]quinazolines as Substrates

140

(1)

1.7.8 Pyrido[1,2-a]quinazolines as Substrates

140

(1)

1.7.9 Pyrido[2,1-b]quinazolines as Substrates

141

(1)

1.7.10 Pyrimido[1,6,5-de]-1,2,4-benzothiadiazines as Substrates

141

(1)

1.7.11 Pyrrolo[1,2-a]quinazolines as Substrates

142

(1)

1.7.12 Pyrrolo[2,1-b]quinazolines as Substrates

142

(1)

1.7.13 Tetrazolo[1,5-c]quinazolines as Substrates

142

(1)

1.7.14 [1,3,4]Thiadiazino[3,2-c]quinazolin-5-iums as Substrates

143

(1)

1.7.15 1,3,4-Thiadiazolo[2,3-b]quinazolines as Substrates

143

(1)

1.7.16 1,3,4-Thiadiazolo[3,2-c]quinazolines as Substrates

143

(1)

1.7.17 [1,4]Thiazino[3,4-b]quinazolines as Substrates

144

(1)

1.7.18 Thiazolo[4,3-b]quinazolines as Substrates

144

(1)

1.7.19 Thioxanthenes as Substrates

144

(1)

1.7.20 [1,2,3]Triazolo[1,5-a]quinazolines as Substrates

145

(1)

1.8 From a Heterotetracyclic Substrate

145

(4)

1.8.1 Benzothiazolo[3,2-a]quinazolines as Substrates

146

(1)

1.8.2 Benzothiazolo[3,2-c]quinazolin-7-iums as Substrates

146

(1)

1.8.3 [1]Benzothiopyrano[4,3,2-de]quinazolines as Substrates

146

(1)

1.8.4 Benzoxazolo[3,2-a]quinazolines as Substrates

147

(1)

1.8.5 Quinazolino[3,2-c][1,2,3]benzotriazines as Substrates

147

(1)

1.8.6 Quinazolino[3,2-a][3,1]benzoxazines as Substrates

148

(1)

1.8.7 Quinazolino[3,2-c][2,3]benzoxazines as Substrates

148

(1)

1.8.8 Quinazolino[1,2-a]quinazolines as Substrates

148

(1)

1.9 From a Heteropentacyclic Substrate

149

(1)

1.9.1 Benz[4,5]isoquino[2,1-a]quinazolines as Substrates

149

(1)

1.9.2 Indolo[2',3',:3,4]pyrido[2,1-b]quinazolines as Substrates

149

(1)

1.10 From a Spiro Heterocyclic Substrate

150

(1)

CHAPTER 2. QUINAZOLINE, ALKYLQUINAZOLINES, AND ARYLQUINAZOLINES

151

(30)

2.1 Quinazoline

151

(7)

2.1.1 Preparation of Quinazoline

151

(1)

2.1.2 Physical Properties of Quinazoline

152

(1)

2.1.3 Reactions of Quinazoline

153

(5)

2.2 C-Alkyl-and C-Arylquinazolines

158

(23)

2.2.1 Preparation of Alkyl-and Arylquinazolines

158

(11)

2.1.1.1 By C-Alkylation

158

(2)

2.2.1.2 By Displacement Reactions

160

(2)

2.2.1.3 By Eliminative Reactions

162

(2)

2.2.1.4 By Interconversion of Alkyl Groups

164

(3)

2.2.1.5 By Modification of Carbaldehydes or Ketones

167

(1)

2.2.1.6 By Rearrangement

167

(1)

2.2.1.7 By Oxidation of Hydro Derivatives

168

(1)

2.2.2 Properties and Reactions of Alkyl-and Arylquinazolines

169

(12)

2.2.2.1 Halogenation at Alkyl Groups

169

(3)

2.2.2.2 Oxidation at Alkyl Groups

172

(2)

2.2.2.3 Mannich Reactions at Alkyl or Aryl Groups

174

(1)

2.2.2.4 Acylations at Alkyl Groups

175

(2)

2.2.2.5 Nitrosation at Alkyl Groups

177

(1)

2.2.2.6 Other Reactions at Alkyl Groups

177

(4)

CHAPTER 3. HALOGENOQUINAZOLINES

181

(38)

3.1 Preparation of 2- or 4-Chloroquinazolines

181

(4)

3.1.1 From Quinazolinones with Phosphoryl Chloride

181

(2)

3.1.2 From Quinazolinones with Phosphorus Pentachloride

183

(1)

3.1.3 From Quinazolinones with a Vilsmeier Reagent

184

(1)

3.2 Preparation 2- or 4-(Bromo, Iodo, or Fluoro) quinazolines

185

(1)

3.3 Preparation 5- to 8-Halogenoquinazolines

186

(2)

3.4 Preparation of Extranuclear Halogenoquinazolines

188

(3)

3.5 Reactions of 2- or 4-Halogenoquinazolines

191

(16)

3.5.1 Aminolysis of 2- or 4-Halogenoquinazolines

191

(9)

3.5.1.1 With Simple 2-Halogenoquinazolines as Substrates

191

(1)

3.5.1.2 With Simple 4-Halogenoquinazolines as Substrates

192

(2)

3.5.1.3 With 2,4-Dihalogenoquinazolines as Substrates

194

(2)

3.5.1.4 With 2-Halogeno-4- or 4-Halogeno-2-quinazolinamines as Substrates

196

(1)

3.5.1.5 With Other 2-Halogeno-4- or 4-Halogeno-2-substituted-quinazolines as Substrates

197

(3)

3.5.2 Alcoholysis of 2- or 4-Halogenoquinazolines

200

(3)

3.5.3 Hydrolysis of 2- or 4-Halogenoquinazolines

203

(1)

3.5.4 Thiolysis or Alkanethiolysis of 2- or 4-Halogenoquinazolines

204

(1)

3.5.5 Other Reactions of 2- or 4-Halogenoquinazolines

205

(2)

3.6 Reactions of 5- to 8-Halogenoquinazolines

207

(3)

3.7 Reactions of Extranuclear Halogenoquinazolines

210

(9)

CHAPTER 4. OXYQUINAZOLINES

219

(68)

4.1 Tautomeric Quinazolinones

219

(23)

4.1.1 Preparation of Tautomeric Quinazolinones

220

(7)

4.1.1.1 From Quinazolinamines

220

(1)

4.1.1.2 From Quinazolinethiones or Derivatives

221

(2)

4.1.1.3 From Alkoxy- or Aryloxy-quinazolines

223

(1)

4.1.1.4 From Other Types of Quinazoline Substrates

224

(1)

4.1.1.5 By Nuclear Oxidation of Quinazolines or Hydroquinazolines

225

(2)

4.1.2 Reactions of Tautomeric Quinazolinones

227

(15)

4.1.2.1 Conversion into Quinazolinethiones

227

(2)

4.1.2.2 O- or N-Acylation and O-Silylation Reactions

229

(2)

4.1.2.3 O- or N-Alkylation Reactions

231

(7)

4.1.2.4 Conversion into Quinazolinamines

238

(1)

4.1.2.5 Nuclear Reduction with or without Deoxygenation

239

(2)

4.1.2.6 Other Reactions

241

(1)

4.2 5- to 8-Quinazolinols

242

(5)

4.2.1 Preparation of Quinazolinols

242

(3)

4.2.2 Reactions of Quinazolinols

245

(2)

4.3 Quinazoline Quinones

247

(3)

4.4 Extranuclear Hydroxyquinazolines

250

(6)

4.4.1 Preparation of Extranuclear Hydroxyquinazolines

250

(3)

4.4.2 Reactions of Extranuclear Hydroxyquinazolines

253

(3)

4.5 Alkoxy- and Aryloxyquinazolines

256

(6)

4.5.1 Preparation of Alkoxy- and Aryloxyquinazolines

256

(2)

4.5.2 Reactions of Alkoxy- and Aryloxyquinazolines

258

(4)

4.5.2.1 Aminolysis of Alkoxyquinazolines

258

(2)

4.5.2.2 Thermal Rearrangement of 2- or 4-Alkoxyquinazolines

260

(1)

4.5.2.3 Hilbert-Johnson Reactions on Trialkylsiloxyquinazolines

261

(1)

4.6 Nontautomeric (Fixed) Quinazolinones

262

(10)

4.6.1 Preparation of Fixed Quinazolinones

262

(3)

4.6.2 Reactions of Fixed Quinazolinones

265

(7)

4.6.2.1 Conversion into Fixed Quinazolinethiones

265

(2)

4.6.2.2 Reductive Reactions

267

(2)

4.6.2.3 Other Reactions

269

(3)

4.7 Quinazoline N-Oxides

272

(8)

4.7.1 Preparation of Quinazoline N-Oxides

272

(2)

4.7.2 Reactions of Quinazoline N-Oxides

274

(6)

4.7.2.1 Deoxygenation

274

(2)

4.7.2.2 O-Acylation or O-Alkylation

276

(2)

4.7.2.3 Reactions Involving Ring Scission

278

(1)

4.7.2.4 Minor Reactions

279

(1)

4.8 Ancillary Aspects of Oxyquinazolines

280

(7)

4.8.1 X-Ray Structural Analyses for Oxyquinazolines

281

(1)

4.8.2 Studies of Fine Structure in Oxyquinazolines

281

(1)

4.8.3 General Spectral and Related Studies on Oxyquinazolines

282

(3)

4.8.4 Naturally Occurring Oxyquinazolines

285

(2)

CHAPTER 5. THIOQUINAZOLINES

287

(34)

5.1 Quinazolinethiones

287

(21)

5.1.1 Preparation of Quinazolinethiones

287

(2)

5.1.2 Reactions of Quinazolinethiones

289

(19)

5.1.2.1 S-Acylation and S-Alkylation

289

(10)

5.1.2.2 Aminolysis

299

(3)

5.1.2.3 Oxidative Reactions

302

(2)

5.1.2.4 Formation of Metal Complexes

304

(1)

5.1.2.5 Other Reactions

305

(3)

5.2 5- to 8-Quinazolinethiols and Extranuclear Mercaptoquinazolines

308

(1)

5.3 Alkylthio- and Arylthioquinazolines

309

(7)

5.3.1 Preparation of Alkylthio- and Arylthioquinazolines

310

(1)

5.3.2 Reactions of Alkylthio- and Arylthioquinazolines

311

(5)

5.4 Diquinazolinyl Disulfides and Sulfides

316

(1)

5.5 Quinazolinesulfonic Acids and Related Derivatives

317

(3)

5.6 Quinazoline Sulfoxides and Sulfones

320

(1)

CHAPTER 6. NITRO, AMINO, AND RELATED QUINAZOLINES

321

(56)

6.1 Nitroquinazolines

321

(8)

6.1.1 Preparation of Nitroquinazolines

320

(4)

6.1.2 Reactions of Nitroquinazolines

324

(5)

6.2 Regular Aminoquinazolines

329

(38)

6.2.1 Preparation of Regular Aminoquinazolines

329

(10)

6.2.2 Reactions of Regular Aminoquinazolines

339

(28)

6.2.2.1 Acylation Reactions

340

(4)

6.2.2.2 Conversion into Schiff Bases

344

(2)

6.2.2.3 Conversion into Alkoxycarbonyl-aminoquinazolines

346

(1)

6.2.2.4 Conversion into Ureidoquinazolines

347

(3)

6.2.2.5 Diazotization and Subsequent Reactions

350

(4)

6.2.2.6 Deamination and Other Displacement Reactions

354

(2)

6.2.2.7 Nuclear N-Alkylation, Oxidation, or Reduction

356

(2)

6.2.2.8 Miscellaneous Reactions of Minor Application

358

(4)

6.2.2.9 Conversion of 3-Amino- into 3-Aziridin-1' -yl-4(3H)-quinazolionones and Related Compounds

362

(4)

6.2.2.10 Ancillary and Biological Aspects

366

(1)

6.3 Hydrazino-, Hydroxyamino-, and Azidoquinazolines

367

(7)

6.3.1 Preparation of Hydrazinoquinazolines

367

(1)

6.3.2 Reactions of Hydrazinoquinazolines

367

(4)

6.3.3 Preparation and Reactions of Hydroxyaminoquinazolines

371

(2)

6.3.4 Preparation, Fine Structure, and Reactions of Azidoquinazolines

373

(1)

6.4 Preparation and Reactions of Nontautomeric Quinazolinimines

374

(1)

6.5 Arylazo-and Nitrosoquinazolines

375

(2)

CHAPTER 7. QUINAZOLINECARBOXYLIC ACIDS AND RELATED DERIVATIVES

377

(30)

7.1 Quinazolinecarboxylic Acids

377

(7)

7.1.1 Preparation of Quinazolinecarboxylic Acids

377

(3)

7.1.2 Reactions of Quinazolinecarboxylic Acids

380

(4)

7.2 Quinazolinecarboxylic Esters

384

(5)

7.2.1 Preparation of Quinazolinecarboxylic Esters

384

(2)

7.2.2 Reactions of Quinazolinecarboxylic Esters

386

(3)

7.3 Quinazolinecarbonyl Chlorides

389

(1)

7.4 Quinazolinecarboxamides and Quinazolinecarbohydrazides

390

(5)

7.5 Quinazolinecarbonitriles

395

(3)

7.6 Quinazolinecarbaldehydes

398

(2)

7.7 Quinazoline Ketones

400

(4)

7.8 Quinazoline Thiocyanates and Isothiocyanates

404

(3)

APPENDIX. TABLE OF SIMPLE QUINAZOLINES

407

(200)

REFERENCES

607

(76)

INDEX

683

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Quinazolines, Volume 55, Supplement 1

Summary

Author Biography

Table of Contents

Supplemental Materials