The Pyridazines, Volume 57, Supplement 1

, by Brown, Desmond J.; Ellman, Jonathan A.; Taylor, Edward C.

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ISBN: 9780471251378 | 0471251372
Cover: Hardcover
Copyright: 1/3/2000

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This new volume substantially updates the original pyridazines volume which was published in 1973. Announcing the latest volume in the successful and prominent Chemistry of Heterocyclic Compounds Series.

Primary Syntheses from Aliphatic or Carbocyclic Synthons

(58)

From a Single Six-Atom Synthon

(15)

By Completion of the N1--N2 Bond

(1)

By Completion of the N2--N3 Bond

(1)

From Hydrazonoalkenes or Related Synthons

(2)

From (Hydrazonomethyl)cycloalkanes or Related Synthons

(1)

From Hydrazonealkanols or Related Synthons

(1)

From Hydrazonoalkanals or Related Synthons

(1)

From Hydrazonoalkanones or Related Synthons

(1)

From Hydrazonoalkanoic Acids or Related Synthons

(2)

From Hydrazonolkanoic Esters or Related Synthons

(1)

From Hydrazonalkanamides or Related Synthons

(1)

From Hydrazonoalkanenitriles or Related Synthons

(2)

Completion of the C3--C4 Bond

(2)

Completion of the C4--C5 Bond

(1)

From Two Synthons

(34)

By Using One-and Five-Atom Synthons

(1)

By Using Two-and Four-Atom Synthons

(1)

Where the Two-Atom Synthon Provides N1 + N2

(1)

Using Hydrazine as the N1--N2 Synthon

(9)

Using Substituted Hydrazines as N1--N2 Synthons

(5)

Using Dialkyl Azodicarboxylates as N1--N2 Synthons

(2)

Using Miscellaneous N1--N2 Synthons

(2)

Where the Two-Atom Synthon Provides N2 + N3

(1)

Where the Two-Atom Synthon Provides C3 + C4

(1)

Using Ethylene Derivatives as C3--C4 Synthons

(4)

Using Acetylene Derivatives as C3--C4 Synthons

(1)

Using Aliphatic Aldehydes or Ketones as C3--C4 Synthons

(1)

Using Aliphatic Acids or Acyl Chlorides as C3--C4 Synthons

(1)

Using Aliphatic Esters as C3--C4 Synthons

(2)

Using Aliphatic Amides or Nitriles as C3--C4 Synthons

(1)

Where the Two-Atom Synthon Provides C4 + C5

(1)

By Using Two 3-Atom Synthons

Where the Synthons Provide N1 + N2 + C3 and C4 + C5 + C6

(3)

Where the Synthons Provide N2 + C3 + C4 and C5 + C6 + N1

(1)

From Three or More Synthons

(1)

Where Three Synthons Provide N1 + N2, C3 + C4, and C5 + C6

(1)

Where Three Synthons Provide N1 + N2 + N3, C4, and C5 + C6

(1)

Appendix: Glance Index to Typical Pyridazines Available from Aliphatic or Carbocyclic Synthons

(8)

Primary Syntheses from Other Heterocyclic Systems

(72)

Pyridazines from Three-, Four-, or Five-Membered Heterocyclic Systems

(12)

Azirines as Substrates

(1)

Furans as Substrates

(5)

Imidazoles as Substrates

(1)

Isoxazoles as Substrates

(1)

Oxazoles as Substrates

(1)

Oxetes as Substrates

(1)

Oxirenes as Substrates

(1)

Pyrazoles as Substrates

(1)

Pyrroles as Substrates

(1)

Thiophenes as Substrates

(2)

1,2,4-Triazoles as Substrates

(1)

Pyridazines from Other Six-Membered Heterocyclic Systems

(12)

1,2-Dioxins or 1,2-Dithiins as Substrates

(1)

1,3-Dioxins as Substrates

(1)

1,3,4-Oxadiazines as Substrates

(1)

Pyrans as Substrates

(1)

Pyridines as Substrates

(1)

Pyrimidines as Substrates

(1)

1,2,4,5-Tetrazines as Substrates

(6)

1,3,4-Thiadiazines as Substrates

(1)

1,2-Thiazines as Substrates

(1)

1,2,3-Triazines as Substrates

(1)

1,2,4-Triazines as Substrates

(1)

Pyridazines from Seven-Membered Heteromonocyclic Systems

(4)

1,2-Diazepines as Substrates

(1)

1,4,5-Selena-or 1,4,5-Thiadiazepines as Substrates

(1)

Thiepines as Substrates

(1)

1,2,5-Triazepines as Substrates

(1)

Pyridazines from Heterobicyclic Systems

(27)

1,2-Benzisoxazoles as Substrates

(1)

Benzofurans as Substrates

(1)

Cycloocta[d]pyridazines as Substrates

(1)

1,2-Diazabicyclo[3.2.0]heptanes as Substrates

(1)

3,4-Diazabicyclo[4.1.0]heptanes as Substrates

(1)

1,2-Diazabicyclo[3.1.0]hexanes as Substrates

(1)

1,6-Diazabicyclo[3.1.0]hexanes as Substrates

(1)

2,3-Diazabicyclo[3.1.0]hexanes as Substrates

(1)

1,3-Dioxolo[4,5-d]pyridazines as Substrates

(1)

Furo[3,2-b]furans as Substrates

(1)

Furo[2,3-d]pyridazines as Substrates

(1)

Furo[3,2-c]pyridazines as Substrates

(1)

Furo[3,4-d]pyridazines as Substrates

(1)

Imidazo[1,2-b]pyridazines as Substrates

(1)

Imidazo[1,5-b]pyridazines as Substrates

(1)

Imidazo[4,5-d]pyridazines as Substrates

(1)

Isoxazolo[3,4-d]pyridazines as Substrates

(2)

Isoxazolo[4,5-d]pyridazines as Substrates

(1)

7-Oxa-3,4-diazabicyclo[4.1.0]heptanes as Substrates

(1)

[1,2,4]Oxadiazolo[2,3-b]pyridazines as Substrates

(1)

1,2,4-Oxadiazolo[4,5-b]pyridazines Substrates

100

(1)

[1,2,5]Oxadiazolo[3,4-d]pyridazines as Substrates

101

(1)

Oxazolo[4,5-d]-and Oxazolo[5,4-c]pyridazines as Substrates

101

(1)

Oxazolo[3,2-b]pyridazin-4-iums as Substrates

102

(1)

Phthalazines as Substrates

103

(1)

Pyrano[2,3-d]pyridazines as Substrates

103

(1)

Pyrazino[2,3-d]pyridazines as Substrates

104

(1)

Pyrazolo[1,2-a]pyridazines as Substrates

104

(1)

Pyrazolo[3,4-d]pyridazines as Substrates

105

(1)

Pyridazino[3,4-d][1,3]oxazines as Substrates

105

(1)

Pyridazino[4,5-d][1,3]oxazines as Substrates

106

(1)

Pyridazino[1,2-a]pyridazines as Substrates

106

(1)

Pyridazino[4,5-d]pyridazines as Substrates

107

(1)

Pyridazino[1,6-a]1,3,5-and Pyridazino[6.1-c][1,2,4] triazines as Substrates

107

(1)

Pyrido[1,2-b]pyridazin-9-iums as Substrates

108

(1)

Pyrimido[4,5-c]pyridazines as Substrates

108

(1)

Pyrimido[4,5-d]pyridazines as Substrates

109

(1)

Pyrrolo[3,2-c]pyridazines as Substrates

109

(1)

Quinolines as Substrates

109

(1)

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

110

(1)

[1,3,4]Thiadiazolo[3,4-a]pyridazines as Substrates

111

(1)

Thiazolo[3,2-b]pyridazin-4-iums as Substrates

111

(1)

Thieno[2,3-c]pyridazines as Substrates

111

(1)

Thieno[3,4-d]pyridazines as Substrates

112

(1)

3,4,7-Triazabicyclo[4.1.0]heptanes as Substrates

112

(1)

[1,2,4]Triazolo[1,2-a]pyridazines as Substrates

113

(1)

Pyridazines from Heterotricyclic Systems

114

(4)

Pyridazines from Heterotetracyclic Systems

118

(1)

Pyridazines from Bridged Heterocyclic Systems

119

(3)

Pyridazines from Spiro Heterocyclic Systems

122

(2)

Appendix: Glance Index to Typical Pyridazines Readily Available from Other Heterocyclic Systems

124

(7)

Pyridazine, Alkylpyridazines, and Arylpyridazines

131

(46)

Pyridazine

131

(9)

Preparation of Pyridazine

131

(1)

Physical Aspects of Pyridazine

132

(2)

Reactions of Pyridazine

134

(6)

C-Alkyl-and C-Arylpyridazines

140

(31)

Preparation of C-Alkyl-and C-Arylpyridazines

140

(1)

By Direct Alkylation

140

(4)

By Nuclear Addition Reactions

144

(3)

By Displacement Reactions

147

(5)

By Elimination of Functional Groups

152

(3)

By Modification of Aldehydes, Ketones, or Esters

155

(2)

By Interconversion of Simple Alkyl Substituents

157

(2)

Properties and Reactions of C-Alkyl-and C-Arylpyridazines

159

(1)

Oxidative Reactions

160

(3)

Extranuclear Alkylation and Alkylidenation

163

(3)

Extranuclear Acylation

166

(1)

Extranuclear Halogenation, Nitration, and Diazo Coupling

167

(1)

Miscellaneous Reactions

168

(3)

N-Alkylpyridazinium Salts and Related Ylides

171

(6)

Preparation of N-Alkylpyridazinium Salts

171

(1)

Preparation of Pyridazinium Ylides

172

(1)

Reactions of N-Alkylpyridazinium Salts

173

(2)

Reactions of Pyridazinium Ylides

175

(2)

Halogenopyridazines

177

(74)

Preparation of Nuclear Halogenopyridazines

177

(16)

Nuclear Halogenopyridazines from Pyridazinones

177

(1)

Using Neat Phosphoryl Chloride

177

(5)

Using Phosphoryl Chloride in a Solvent

182

(1)

Using Phosphorus Pentachloride in Phosphoryl Chloride

182

(2)

Using Phosphoryl Chloride and a Tertiary Base

184

(1)

Using Phosphoryl Bromide or Phosphorus Pentabromide

185

(1)

Using Other Reagents

185

(2)

Nuclear Halogenopyridazines by Direct Halogenation

187

(1)

Nuclear Halogenopyridazines from Metallopyridazines

188

(1)

Nuclear Halogenopyridazines from Nitropyridazines

189

(1)

Nuclear Halogenopyridazines by Transhalogenation

190

(2)

Nuclear Halogenopyridazines from Pyridazinamines

192

(1)

Reactions of Nuclear Halogenopyridazines

193

(44)

Aminolysis of Nuclear Halogenopyridazines

193

(1)

3/6-Monohalogenopyridazines as Substrates

193

(6)

4/5-Monohalogenopyridazines as Substrates

199

(3)

3,4/5,6-Dihalogenopyridazines as Substrates

202

(1)

3,5/4,6-Dihalogenopyridazines as Substrates

203

(1)

3,6-Dihalogenopyridazines as Substrates

203

(5)

4,5-Dihalogenopyridazines as Substrates

208

(1)

3,4,5/4,5,6-Trihalogenopyridazines as Substrates

209

(3)

3,4,5,6-Tetrahalogenopyridazines as Substrates

212

(1)

Hydrolysis of Nuclear Halogenopyridazines

213

(3)

Alcoholysis of Nuclear Halogenopyridazines

216

(5)

Thiolysis of Nuclear Halogenopyridazines

221

(2)

Alkanethiolysis of Nuclear Halogenopyridazines

223

(5)

Conversion of Nuclear Halogeno-into Azidopyridazines

228

(3)

Hydrogenolysis of Nuclear Halogenopyridazines

231

(3)

Other Displacement Reactions of Nuclear Halogenopyridazines

234

(1)

Reactions Involving Ring Fission of Nuclear Halogenopyridazines

235

(2)

Preparation of Extranuclear Halogenopyridazines

237

(5)

Extranuclear Halogenopyridazines from the Corresponding Hydroxypyridazines

237

(3)

Extranuclear Halogenopyridazines by Halogenation

240

(1)

Extranuclear Halogenopyridazines by Passenger Halogenation

241

(1)

Reactions of Extranuclear Halogenopyridazines

242

(9)

Aminolysis of Extranuclear Halogenopyridazines

242

(1)

Alcoholysis of Extranuclear Halogenopyridazines

243

(1)

Thiolysis of Extranuclear Halogenopyridazines

244

(1)

Alkanethiolysis of Extranuclear Halogenopyridazines

245

(1)

Hydrogenolysis of Extranuclear Halogenopyridazines

246

(1)

Other Displacement Reactions of Extranuclear Halogenopyridazines

246

(5)

Oxypyridazines

251

(72)

Tautomeric Pyridazinones

252

(21)

Preparation of Tautomeric Pyridazinones

252

(5)

Reactions of Tautomeric Pyridazinones

257

(1)

Conversion into Pyridazinethiones

257

(2)

Conversion into O-or N-Alkyl Derivatives

259

(8)

Conversion into O-or N-Acyl Derivatives

267

(2)

Reductive Reactions

269

(1)

Miscellaneous Reactions

270

(3)

Pyridazine Quinones

273

(3)

Extranuclear Hydroxypyridazines

276

(7)

Preparation of Extranuclear Hydroxypyridazines

276

(4)

Reactions of Extranuclear Hydroxypyridazines

280

(3)

Nuclear and Extranuclear Alkoxy-and Aryloxypyridazines

283

(9)

Preparation of Alkoxy-and Aryloxypyridazines

283

(4)

Reactions of Alkoxy-and Aryloxypyridazines

287

(1)

Aminolysis and Related Processes

287

(1)

Thermal Rearrangement

288

(1)

Hilbert-Johnson Reaction

289

(1)

Other Reactions, Including Those of Epoxides

290

(2)

Nontautomeric Pyridazinones and N-Alkylpyridaziniumolates

292

(10)

Preparation of Nontautomeric Pyridazinones

292

(3)

Reactions of Nontautomeric Pyridazinones

295

(7)

Pyridazine N-Oxides

302

(9)

Preparation of Pyridazine N-Oxides

302

(2)

Reactions of Pyridazine N-Oxides

304

(7)

Ancillary Aspects of Oxypyridazines

311

(12)

X-Ray Structural Analyses of Oxypyridazines

312

(2)

Studies of Fine Structure in Oxypyridazines

314

(1)

General Spectral and Related Studies on Oxypyridazines

315

(2)

Trivial Names for Pyridazine Derivatives

317

(6)

Thiopyridazines

323

(20)

Pyridazinethiones and Pyridazinethiols

323

(11)

Preparation of Pyridazinethiones and Pyridazinethiols

323

(2)

Reactions of Pyridazinethiones and Pyridazinethiols

325

(1)

S-Acylation

326

(1)

S-Alkylation

326

(5)

N-Alkylation

331

(1)

Aminolysis

331

(1)

Oxidation to Dipyridazinyl Disulfides

332

(1)

Other Reactions

333

(1)

Alkylthiopyridazines and Dipyridazinyl Sulfides

334

(5)

Preparation of Alkylthiopyridazines

334

(1)

Reactions of Alkylthiopyridazines

335

(1)

Oxidation to Sulfoxides or Sulfones

335

(1)

Miscellaneous Minor Reactions

336

(3)

Dipyridazinyl Disulfides and Pyridazinesulfonic Acids or Related Compounds

339

(1)

Pyridazine Sulfoxides and Sulfones

340

(3)

Nitro-, Amino-, and Related Pyridazines

343

(44)

Nitropyridazines

343

(5)

Preparation of Nitropyridazines

343

(1)

Reactions of Nitropyridazines

344

(1)

Reduction

344

(3)

Displacement Reactions

347

(1)

Regular Aminopyridazines

348

(23)

Preparation of Regular Aminopyridazines

348

(7)

Reactions of Regular Aminopyridazines

355

(1)

N-Acylation and Subsequent Reactions

356

(3)

N-Alkylidenation and Subsequent Reactions

359

(1)

N-Alkylation Reactions

360

(3)

Conversion into Ureidopyridazines or Related Products

363

(3)

Miscellaneous Reactions

366

(3)

Ancillary Information

369

(2)

Hydrazino-, Hydroxyamino-, and Azidopyridazines

371

(13)

Preparation of Hydrazinopyridazines

371

(2)

Reactions of Hydrazinopyridazines

373

(7)

Preparation and Reactions of Hydroxyaminopyridazines

380

(1)

Preparation, Isomerization, and Reactions of Azidopyridazines

381

(3)

Preparation and Reactions of Nontautomeric Pyridazinimines

384

(2)

Preparation and Reactions of Arylazopyridazines

386

(1)

Pyridazinecarboxylic Acids and Related Derivatives

387

(48)

Pyridazinecarboxylic acids

387

(10)

Preparation of Pyridazinecarboxylic Acids

387

(5)

Reactions of Pyridazinecarboxylic Acids

392

(5)

Pyridazinecarboxylic Esters

397

(10)

Preparation of Pyridazinecarboxylic Esters

397

(4)

Reactions of Pyridazinecarboxylic Esters

401

(6)

Preparation and Reactions of Pyridazinecarbonyl Halides

407

(2)

Preparation and Reactions of Pyridazinecarboxamides

409

(4)

Preparation and Reactions of Pyridazinecarbohydrazides.

413

(2)

Preparation and Reactions of Azidocarbonylpyridazines

415

(1)

Pyridazinecarbonitriles

416

(8)

Preparation of Pyridazinecarbonitriles

417

(3)

Reactions of Pyridazinecarbonitriles

420

(4)

Pyridazinecarbaldehydes

424

(5)

Preparation of Pyridazinecarbaldehydes

424

(1)

Reactions of Pyridazinecarbaldehydes

425

(4)

Pyridazine Ketones

429

(6)

Preparation of Pyridazine Ketones

429

(1)

Reactions of Pyridazine Ketones

430

(5)

Appendix Table of Simple Pyridazines

435

(134)

References

569

(64)

Index

633

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The Pyridazines, Volume 57, Supplement 1

Summary

Author Biography

Table of Contents

Supplemental Materials