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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