Detailed table of contents (pdf)
Detailed table of contents (pdf) Detailed table of contents (pdf)
XXVIII Table of Contents 17.2.2.1.1.2.4.1 Method 1: Reactions of Ethanedial Hydrazone Oximes with Ortho Esters or Related One-Carbon Donors ................ 374 17.2.2.1.1.2.4.1.1 Variation 1: Condensation of Hydrazono(phenyl)acetaldehyde Oxime with Aldehydes ........................................... 375 17.2.2.1.1.2.4.2 Method 2: Synthesis of [1,2,3]Triazolo[5,1-f][1,2,4]triazine ............. 376 17.2.2.1.1.2.4.3 Method 3: Cyclization of 4-Hydrazonopyrazol-3(4H)-amines with Acyl Nitriles .......................................... 376 17.2.2.1.1.2.4.4 Method 4: Reactions of Iminophosphoranes with Isocyanates .......... 376 17.2.2.1.1.2.5 Fragments C—C—N—N—C and N ........................................... 377 17.2.2.1.1.2.5.1 Method 1: Cyclization of 2-Acylhydrazono Ketones with Ammonia or Ammonium Acetate .................................... 377 17.2.2.1.1.2.5.1.1 Variation 1: Cyclization of (N,N-Dimethylamino)ethylenehydrazones and Related Compounds with Ammonium Acetate .............. 378 17.2.2.1.1.2.5.2 Method 2: Cyclization of 1,2-Diketone Monohydrazones with Hydroxylamine ............................................ 379 17.2.2.1.1.2.5.3 Method 3: Reactions of 3,5-Disubstituted 4-Nitrosopyrazoles with Phosphorus Pentachloride ............................ 379 17.2.2.1.1.2.5.4 Method 4: Cyclization of Uracil Hydrazones with Potassium Nitrate ..... 379 17.2.2.1.1.2.5.4.1 Variation 1: Microwave Reactions of 2-Hydrazinoquinolines with Nitrous Acid .............................................. 380 17.2.2.1.1.2.5.5 Method 5: Reaction of 1-Phenyl-3-(pyrrol-1-yl)pyrazol-4-amine with Nitrous Acid ......................................... 380 17.2.2.1.1.3 By Formation of One N—C Bond ........................................... 381 17.2.2.1.1.3.1 Fragment C—C—N—N—C—N ............................................... 381 17.2.2.1.1.3.1.1 Method 1: Photolysis of 1,2-Bis(2-diazido-1-phenylethylidene)diazine .. 381 17.2.2.1.1.3.1.2 Method 2: Cyclization of N-(1-Phenylethylidene)guanidin-2-amines .... 381 17.2.2.1.1.3.1.3 Method 3: Cyclization of 1-Cyanoalkanone 1-Aminoalkylidenehydrazones .................................................... 382 17.2.2.1.1.4 Fragment N—C—C—N—N—C ............................................... 382 17.2.2.1.1.4.1 Method 1: Cyclization of a-[1,2-Bis(ethoxycarbonyl)hydrazino]a-(ethoxycarbonyl)acetimidamide ......................... 382 17.2.2.1.1.4.1.1 Variation 1: Cyclization of 3-(Acylhydrazino)pyridin-2-amines ........... 382 17.2.2.1.2 Annulation by the Formation of a Second Heterocyclic Ring ................. 383 17.2.2.1.2.1 Method 1: From 1,2,4-Triazine-5,6-diamines .......................... 383 17.2.2.1.2.2 Method 2: From 3-Hydrazino-1,2,4-triazines .......................... 383 17.2.2.1.2.2.1 Variation 1: Synthesis of 1,2,4-Triazolo[3,4-c][1,2,4]triazine 7-Oxide ..... 384 17.2.2.1.2.3 Method 3: Synthesis of Pyrazino[2,3-e][1,2,4]triazines ................. 384 17.2.2.1.2.4 Method 4: Cyclization of 5-Acyl-1,2,4-triazines with Arylhydrazines ..... 385 17.2.2.1.2.5 Method 5: Cyclization of 3-Allylamino-1,2,4-triazine with Bromine ..... 385 17.2.2.1.3 Synthesis by Ring Transformation .......................................... 386 17.2.2.1.3.1 Method 1: Oxidation of Imidazole-1,2-diamines ....................... 386 17.2.2.1.3.2 Method 2: Acidic Rearrangement of 2-(Hydroxyimino)imidazol-5-imines ........................ 386
Table of Contents XXIX 17.2.2.1.3.3 Method 3: Reactions of Pyrazolo[3,4-e][1,2,4]oxadiazine with Amines .............................................. 387 17.2.2.1.3.4 Method 4: Reactions of 1,2,4,5-Tetrazines with Imidates or Thioimidates .................................. 387 17.2.2.1.3.4.1 Variation 1: Reactions of 1,2,4,5-Tetrazines with Cyanimides ............ 388 17.2.2.1.3.5 Method 5: Intramolecular Cycloaddition of Cyano-1,2,4,5-tetrazines ... 389 17.2.2.1.3.6 Method 6: Reactions of 1,2,4,5-Tetrazines with N-(Trimethylsilyl)aldimines Followed by Oxidation ..................................... 389 17.2.2.1.3.6.1 Variation 1: Reactions of 1,2,4,5-Tetrazines with Benzaldehyde O-Methyloximes .......................................... 390 17.2.2.1.3.7 Method 7: Reactions of 1,2,4,5-Tetrazines with Dimethylamine ........ 390 17.2.2.1.4 Aromatization ............................................................ 390 17.2.2.1.4.1 Method 1: Conversion of 1,2,4-Triazin-5(2H)-ones or 1,2,4-Triazine-5(2H)-thiones into 1,2,4-Triazines ............ 391 17.2.2.1.5 Synthesis by Substituent Modification ..................................... 392 17.2.2.1.5.1 Substitution of Existing Substituents ....................................... 392 17.2.2.1.5.1.1 Of Hydrogen .............................................................. 392 17.2.2.1.5.1.1.1 Method 1: Lithiation ................................................. 392 17.2.2.1.5.1.1.2 Method 2: Reactions with Grignard Reagents ......................... 393 17.2.2.1.5.1.1.2.1 Variation 1: Reactions with Enolate Anions ............................. 394 17.2.2.1.5.1.1.2.2 Variation 2: Reactions with Nitroalkanes and Base ...................... 395 17.2.2.1.5.1.1.2.3 Variation 3: Reactions with Chloromethyl Phenyl Sulfone and Base ...... 395 17.2.2.1.5.1.1.3 Method 3: Reactions with Hydrogen Cyanide .......................... 396 17.2.2.1.5.1.1.4 Method 4: Vicarious Nucleophilic Substitution ......................... 396 17.2.2.1.5.1.1.5 Method 5: Dimerization to 5,5¢-Bi(1,2,4-triazines) ..................... 398 17.2.2.1.5.1.1.6 Method 6: Coupling with Arenes and Indoles .......................... 398 17.2.2.1.5.1.1.7 Method 7: Electrophilic Halogenation of 1,2,4-Triazine N-Oxides ....... 399 17.2.2.1.5.1.1.8 Method 8: By Nucleophilic Substitution with Ammonia, Amines, and Related Nucleophiles .................................. 399 17.2.2.1.5.1.1.8.1 Variation 1: Other Chichibabin-Type Reactions ......................... 400 17.2.2.1.5.1.1.8.2 Variation 2: Reactions with Hydrazine .................................. 401 17.2.2.1.5.1.1.8.3 Variation 3: C3-Amination of 1,2,4-Triazine 4-Oxides .................... 401 17.2.2.1.5.1.2 Of Carbon Functionalities ................................................. 402 17.2.2.1.5.1.2.1 Method 1: Decarboxylation of 1,2,4-Triazine-3-carboxylic Acid ......... 402 17.2.2.1.5.1.2.2 Method 2: Reactions of 3-Trichloromethyl-1,2,4-triazines with Nucleophiles .............................................. 402 17.2.2.1.5.1.2.3 Method 3: Reactions of 1,2,4-Triazinecarbonitriles with Nucleophiles ... 402 17.2.2.1.5.1.3 Of Heteroatoms .......................................................... 403 17.2.2.1.5.1.3.1 Method 1: Reactions of Chloro-1,2,4-triazines with Nucleophiles ....... 403 17.2.2.1.5.1.3.1.1 Variation 1: Reactions of 3-Bromo-1,2,4-triazine 2-Oxides with Nucleophiles ......................................... 404 17.2.2.1.5.1.3.1.2 Variation 2: Reactions of Alkoxy-1,2,4-triazines with Nucleophiles ....... 404 17.2.2.1.5.1.3.1.3 Variation 3: Reactions of 3-Substituted 1,2,4-Triazine N-Oxides with Nucleophiles ......................................... 405
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- Page 29 and 30: Table of Contents XXXVII 17.2.3.1.4
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- Page 35 and 36: Table of Contents XLIII 17.4.4.1.2.
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XXVIII Table <strong>of</strong> Contents<br />
17.2.2.1.1.2.4.1 Method 1: Reactions <strong>of</strong> Ethanedial Hydrazone Oximes with<br />
Ortho Esters or Related One-Carbon Donors ................ 374<br />
17.2.2.1.1.2.4.1.1 Variation 1: Condensation <strong>of</strong> Hydrazono(phenyl)acetaldehyde Oxime<br />
with Aldehydes ........................................... 375<br />
17.2.2.1.1.2.4.2 Method 2: Synthesis <strong>of</strong> [1,2,3]Triazolo[5,1-f][1,2,4]triazine ............. 376<br />
17.2.2.1.1.2.4.3 Method 3: Cyclization <strong>of</strong> 4-Hydrazonopyrazol-3(4H)-amines<br />
with Acyl Nitriles .......................................... 376<br />
17.2.2.1.1.2.4.4 Method 4: Reactions <strong>of</strong> Iminophosphoranes with Isocyanates .......... 376<br />
17.2.2.1.1.2.5 Fragments C—C—N—N—C and N ........................................... 377<br />
17.2.2.1.1.2.5.1 Method 1: Cyclization <strong>of</strong> 2-Acylhydrazono Ketones with Ammonia<br />
or Ammonium Acetate .................................... 377<br />
17.2.2.1.1.2.5.1.1 Variation 1: Cyclization <strong>of</strong> (N,N-Dimethylamino)ethylenehydrazones and<br />
Related Compounds with Ammonium Acetate .............. 378<br />
17.2.2.1.1.2.5.2 Method 2: Cyclization <strong>of</strong> 1,2-Diketone Monohydrazones with<br />
Hydroxylamine ............................................ 379<br />
17.2.2.1.1.2.5.3 Method 3: Reactions <strong>of</strong> 3,5-Disubstituted 4-Nitrosopyrazoles<br />
with Phosphorus Pentachloride ............................ 379<br />
17.2.2.1.1.2.5.4 Method 4: Cyclization <strong>of</strong> Uracil Hydrazones with Potassium Nitrate ..... 379<br />
17.2.2.1.1.2.5.4.1 Variation 1: Microwave Reactions <strong>of</strong> 2-Hydrazinoquinolines with<br />
Nitrous Acid .............................................. 380<br />
17.2.2.1.1.2.5.5 Method 5: Reaction <strong>of</strong> 1-Phenyl-3-(pyrrol-1-yl)pyrazol-4-amine<br />
with Nitrous Acid ......................................... 380<br />
17.2.2.1.1.3 By Formation <strong>of</strong> One N—C Bond ........................................... 381<br />
17.2.2.1.1.3.1 Fragment C—C—N—N—C—N ............................................... 381<br />
17.2.2.1.1.3.1.1 Method 1: Photolysis <strong>of</strong> 1,2-Bis(2-diazido-1-phenylethylidene)diazine .. 381<br />
17.2.2.1.1.3.1.2 Method 2: Cyclization <strong>of</strong> N-(1-Phenylethylidene)guanidin-2-amines .... 381<br />
17.2.2.1.1.3.1.3 Method 3: Cyclization <strong>of</strong> 1-Cyanoalkanone 1-Aminoalkylidenehydrazones<br />
.................................................... 382<br />
17.2.2.1.1.4 Fragment N—C—C—N—N—C ............................................... 382<br />
17.2.2.1.1.4.1 Method 1: Cyclization <strong>of</strong> a-[1,2-Bis(ethoxycarbonyl)hydrazino]a-(ethoxycarbonyl)acetimidamide<br />
......................... 382<br />
17.2.2.1.1.4.1.1 Variation 1: Cyclization <strong>of</strong> 3-(Acylhydrazino)pyridin-2-amines ........... 382<br />
17.2.2.1.2 Annulation by the Formation <strong>of</strong> a Second Heterocyclic Ring ................. 383<br />
17.2.2.1.2.1 Method 1: From 1,2,4-Triazine-5,6-diamines .......................... 383<br />
17.2.2.1.2.2 Method 2: From 3-Hydrazino-1,2,4-triazines .......................... 383<br />
17.2.2.1.2.2.1 Variation 1: Synthesis <strong>of</strong> 1,2,4-Triazolo[3,4-c][1,2,4]triazine 7-Oxide ..... 384<br />
17.2.2.1.2.3 Method 3: Synthesis <strong>of</strong> Pyrazino[2,3-e][1,2,4]triazines ................. 384<br />
17.2.2.1.2.4 Method 4: Cyclization <strong>of</strong> 5-Acyl-1,2,4-triazines with Arylhydrazines ..... 385<br />
17.2.2.1.2.5 Method 5: Cyclization <strong>of</strong> 3-Allylamino-1,2,4-triazine with Bromine ..... 385<br />
17.2.2.1.3 Synthesis by Ring Transformation .......................................... 386<br />
17.2.2.1.3.1 Method 1: Oxidation <strong>of</strong> Imidazole-1,2-diamines ....................... 386<br />
17.2.2.1.3.2 Method 2: Acidic Rearrangement <strong>of</strong><br />
2-(Hydroxyimino)imidazol-5-imines ........................ 386