Cinnolines and Phthalazines: Supplement II, Volume 64

CINNOLINES AND PHTHALAZINES Supplement II......Page 3
Preface......Page 11
Contents......Page 13
1.1.1 By Formation of the N1–C8a Bond......Page 19
1.1.2 By Formation of the N1–N2 Bond......Page 21
1.1.3 By Formation of the N2–C3 Bond......Page 22
1.1.4 By Formation of the C3–C4 Bond......Page 24
1.1.5 By Formation of the C4–C4a Bond......Page 25
1.2.1 When the Synthon Supplies N2 of the Cinnoline......Page 30
1.2.2 When the Synthon Supplies N1 + N2 of the Cinnoline......Page 33
1.2.3 When the Synthon Supplies N2 + C3 of the Cinnoline......Page 36
1.2.4 When the Synthon Supplies C3 + C4 of the Cinnoline......Page 37
1.2.5 When the Synthon Supplies N1 + N2 + C3 + C4 of the Cinnoline......Page 39
1.3 From a Pyridazine Substrate......Page 40
1.4 From Other Heteromonocyclic Substrates......Page 42
1.5 From Heterobicyclic Substrates......Page 43
1.6 From Heteropolycyclic Substrates......Page 46
1.7 Glance Index to Typical Cinnolines Derivatives Available by Primary Syntheses......Page 48
2.1.1 Preparation of Cinnoline and Hydrocinnolines......Page 51
2.1.2 Physical Properties of Cinnoline......Page 52
2.1.3 Reactions of Cinnoline......Page 53
2.2 Alkyl- and Arylcinnolines......Page 54
2.2.1 Preparation of Alkyl- and Arylcinnolines......Page 55
2.2.2 Reactions of Alkyl- and Arylcinnolines......Page 60
3.1 Preparation of Halogenocinnolines......Page 63
3.2 Reactions of Halogenocinnolines......Page 67
CHAPTER 4 OXYCINNOLINES......Page 77
4.1.1 Preparation of Tautomeric Cinnolinones......Page 78
4.1.2.1 Alkylation of Tautomeric Cinnolinones......Page 80
4.1.2.2 Other Reactions of Tautomeric Cinnolinones......Page 83
4.2 Other Oxycinnolines......Page 87
5.1 Cinnolinethiones......Page 97
5.2 Other Thiocinnolines......Page 99
6.1 Nitrocinnolines......Page 103
6.2.1 Preparation of Amino-, Hydrazino-, and Arylazocinnolines......Page 105
6.2.2 Reactions of Amino- and Hydrazinocinnolines......Page 108
7.1.1 Preparation of Cinnolinecarboxylic Acids......Page 113
7.1.2 Reactions of Cinnolinecarboxylic Acids......Page 116
7.2 Cinnolinecarboxylic Esters......Page 119
7.3 Cinnolinecarboxamides and Cinnolinecarbohydrazides......Page 120
7.4 Cinnolinecarbonitriles......Page 121
7.5 Cinnoline Aldehydes and Ketones......Page 123
8.1.1 By Formation of the C1–C8a Bond......Page 127
8.1.2 By Formation of the C1–N2 Bond......Page 130
8.2.1 Where the Synthon Supplies C1 of the Phthalazine......Page 131
8.2.2.1 Using 1,2-Dialkylbenzenes as Substrates......Page 132
8.2.2.3 Using 1-Alkyl-2-halogenoformylbenzenes as Substrates......Page 133
8.2.2.5 Using 1-Aldehydo-2-ketobenzenes as Substrates......Page 134
8.2.2.6 Using 1-Aldehydo-2-carboxybenzenes as Substrates......Page 135
8.2.2.9 Using 1,2-Diketobenzenes as Substrates......Page 136
8.2.2.10 Using 1-Keto-2-carboxybenzenes as Substrates......Page 138
8.2.2.11 Using 1-Keto-2-alkoxycarbonylbenzenes as Substrates......Page 143
8.2.2.13 Using 1,2-Dicarboxybenzenes (Phthalic Acids) as Substrates......Page 144
8.2.2.15 Using 1,2-Dialkoxycarbonylbenzenes (Phthalic Esters) as Substrates......Page 145
8.2.3 Where the Synthon Supplies C1 + N2 + N3 of the Phthalazine......Page 147
8.3 From Other Carbocyclic Derivatives as Substrates......Page 148
8.4 From Pyridazine Derivatives as Substrates......Page 150
8.5 From 1,2,4,5-Tetrazines as Substrates......Page 153
8.6.2 2-Benzopyrans as Substrates......Page 156
8.6.3 3,2,4-Benzothiadiazepines as Substrates......Page 157
8.6.4 2,3-Benzoxazines as Substrates......Page 158
8.6.6.1 Using 1,3-Dihydro-1,3-isobenzofurandiones (Phthalic Anhydrides)......Page 159
8.6.6.2 Using 1,3-Dihydro-1-isobenzofuranones (Phthalides)......Page 162
8.6.7.1 Using N-Unsubstituted-1,3-isoindolinediones......Page 168
8.6.7.2 Using N-Alkyl-1,3-isoindolinediones......Page 169
8.6.7.4 Using 3-Hydroxy-1-isoindolinones......Page 170
8.6.7.5 Using 1,3-Isoindolinediimines or 3-Imino-1-isoindolinones......Page 171
8.6.7.6 Using N-Amino-1,3-isoindolinediones......Page 172
8.6.9 Pyridazino[4,5-d]pyridazines as Substrates......Page 175
8.6.10 Thieno[3,4-d]pyridazines as Substrates......Page 176
8.7 From Heteropolycyclic Derivatives as Substrates......Page 177
8.8 From Spiro Heterocyclic Substrates......Page 183
8.9 Glance Index to Typical Phthalazine Derivatives Available by Primary Syntheses......Page 184
9.1.1 Preparation of Phthalazine and Hydrophthalazines......Page 191
9.1.3 Reactions of Phthalazine......Page 193
9.2.1 Preparation of Alkyl- and Arylphthalazines......Page 202
9.2.2 Reactions of Alkyl- and Arylphthalazines......Page 208
9.3.1 Preparation of N-Alkylphthalazinium Salts and the Like......Page 214
9.3.2 Reactions of N-Alkylphthalazinium Salts and the Like......Page 215
10.1.1 From Tautomeric Phthalazinones by Halogenolysis......Page 221
10.1.2 From Other Substrates......Page 224
10.2 Preparation of Extranuclear Halogenophthalazines......Page 226
10.3.1 Hydrogenolysis of Halogenophthalazines......Page 228
10.3.2 Aminolysis of Halogenophthalazines......Page 230
10.3.3 Hydrolysis, Alcoholysis, or Phenolysis of Halogenophthalazines......Page 240
10.3.4 Thiolysis, Alkanethiolysis, or Arenesulfinolysis of Halogenophthalazines......Page 244
10.3.5 Cyanolysis or Aroyl Displacement of Halogenophthalazines......Page 247
10.3.6 Ring Fission and Cyclization Reactions of Halogenophthalazines......Page 248
CHAPTER 11 OXYPHTHALAZINES......Page 253
11.1.1 Preparation of Tautomeric Phthalazinones......Page 254
11.1.2 Reactions of Tautomeric Phthalazinones......Page 256
11.1.2.1 Alkylation or Arylation of Tautomeric Phthalazinones......Page 257
11.1.2.2 Acylation of Tautomeric Phthalazinones......Page 264
11.1.2.3 Reductive and Oxidative Reactions of Tautomeric Phthalazinones......Page 265
11.1.2.4 Other Reactions of Tautomeric Phthalazinones......Page 267
11.2.1 Preparation of Extranuclear Hydroxyphthalazines......Page 270
11.2.2 Reactions of Extranuclear Hydroxyphthalazines......Page 277
11.3.1 Preparation of Phthalazinequinones......Page 281
11.3.2 Reactions of Phthalazinequinones......Page 282
11.4.1 Preparation of Alkoxy- and Aryloxyphthalazines......Page 285
11.4.2 Reactions of Alkoxy- and Aryloxyphthalazines......Page 287
11.5.1 Preparation of Nontautomeric Phthalazinones and Phthalaziniumolates......Page 289
11.5.2 Reactions of Nontautomeric Phthalazinones and Phthalaziniumolates......Page 290
11.6 Phthalazine N-Oxides......Page 294
12.1.2 Reactions of Phthalazinethiones and Phthalazinethiols......Page 299
12.2 Alkylthiophthalazines......Page 302
12.3 Alkylsulfinyl- and Alkylsulfonylphthalazines......Page 305
12.4 Phthalazinesulfonic Acid Derivatives......Page 306
13.1.1 Preparation of Nitrophthalazines......Page 309
13.1.2 Reactions of Nitrophthalazines......Page 310
13.2.1 Preparation of Aminophthalazines......Page 313
13.2.2 Reactions of Aminophthalazines......Page 317
13.3.1 Preparation of Hydrazinophthalazines......Page 328
13.3.2.2 N´-Acylation, Arylation, or Carbamoylation and Subsequent Reactions......Page 329
13.3.2.3 Alkylidenation and Subsequent Reactions......Page 331
13.3.2.4 Cyclization Reactions......Page 334
14.1.1 Preparation of Phthalazinecarboxylic Acids......Page 337
14.1.2 Reactions of Phthalazinecarboxylic Acids......Page 340
14.2 Phthalazinecarbonyl Halides......Page 345
14.3.1 Preparation of Phthalazinecarboxylic Esters......Page 347
14.3.2 Reactions of Phthalazinecarboxylic Esters......Page 348
14.4.1 Preparation of Phthalazine Amides......Page 352
14.4.2 Reactions of Phthalazine Amides......Page 354
14.5.1 Preparation of Phthalazinecarbonitriles......Page 357
14.5.2 Reactions of Phthalazinecarbonitriles......Page 358
14.6 Phthalazine Aldehydes and Ketones......Page 362
APPENDIX: TABLES OF SIMPLE CINNOLINES AND SIMPLE PHTHALAZINES......Page 367
Table A.1 Alphabetical List of Simple Cinnolines Reported Before 2005......Page 369
Table A.2 Alphabetical List of Simple Phthalazines Reported Before 2005......Page 392
REFERENCES......Page 431
INDEX......Page 463