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Table of Contents XXIII
17.2.1.2.1.1.1.4.3 Variation 3: Diazotization of 2-(2-Aminophenyl)quinazolin-4-amines and
2-(2-Aminophenyl)-1,3,5-triazine-4,6-diamines ............. 275
17.2.1.2.1.1.2 By Formation of One N—N and One N—C Bond ............................. 275
17.2.1.2.1.1.2.1 Method 1: Diazotization of Ethyl Aminohetarenecarboxylates and
Alkyl 2-Aminobenzcarboxylates/Cyclization
with Ammonia and Primary Amines ........................ 275
17.2.1.2.1.1.2.1.1 Variation 1: Diazotization of 2-Aminobenzonitrile or Aminohetarenecarbonitriles/Cyclization
with Primary Amines .............. 279
17.2.1.2.1.1.2.2 Method 2: Nitrosation of Methylhetarenamines ....................... 280
17.2.1.2.1.1.2.2.1 Variation 1: Nitrosation of Ethyl (1-Methylindol-2-yl)acetate ............ 282
17.2.1.2.1.1.3 By Formation of Two N—C Bonds .......................................... 282
17.2.1.2.1.1.3.1 Method 1: Cyclization of Pyrazol-1-amines and 1,2,3-Triazol-N-amines
with C—C—C Fragments ................................... 282
17.2.1.2.1.1.4 By Formation of One N—N Bond ........................................... 284
17.2.1.2.1.1.4.1 Method 1: Oxidation of 2-(Aminophenyl) Ketone Hydrazones .......... 284
17.2.1.2.1.1.4.2 Method 2: Oxidation of 2-Nitrobenzaldehyde Hydrazones ............. 284
17.2.1.2.1.1.4.3 Method 3: Cyclization of N-Aroyl-2-azidobenzamides .................. 285
17.2.1.2.1.1.4.4 Method 4: Cyclization of Diazoazolecarboxamides ..................... 286
17.2.1.2.1.1.4.4.1 Variation 1: Cyclization of 5-Diazoimidazole-4-carbonitrile .............. 288
17.2.1.2.1.1.5 By Formation of One N—C Bond ........................................... 288
17.2.1.2.1.1.5.1 Method 1: Cyclization of Azidohetarenecarbonyl Compounds .......... 288
17.2.1.2.1.1.5.2 Method 2: Cyclization of Pyrazol-1-ylaminomethylene Meldrum s Acid . 289
17.2.1.2.1.1.6 By Formation of One C—C Bond ........................................... 289
17.2.1.2.1.1.6.1 Method 1: Cyclization of 1-Aryl-3,3-dialkyltriazenes ................... 289
17.2.1.2.1.2 By Annulation to the 1,2,3-Triazine Ring ................................... 290
17.2.1.2.1.2.1 Method 1: Annulation with (Chlorocarbonyl)phenylketene ............. 290
17.2.1.2.1.2.2 Method 2: Cyclization of Annulated N-(2-Nitrophenyl)-1,2,3-triazines ... 290
17.2.1.2.1.2.3 Method 3: Reaction of 1,2,3-Benzotriazin-4(3H)-one or
1,2,3-Benzotriazine-4(3H)-thione with a-Halo Ketones ...... 290
17.2.1.2.1.2.4 Method 4: Cyclization of 4-(w-Chloroalkylamino)pyrimido[5,4-d]-
[1,2,3]triazines ............................................ 291
17.2.1.2.1.2.5 Method 5: Condensation Reactions of Annulated 4-Hydrazino-
1,2,3-triazines ............................................ 291
17.2.1.2.1.2.6 Method 6: Thermolysis of 1,2,3-Benzotriazin-4(3H)-one ................ 292
17.2.1.2.1.2.7 Method 7: Condensation Reactions of 4-Aroyl-5-ethoxy-1,2,3-triazines . 292
17.2.1.2.2 Synthesis by Ring Transformation .......................................... 293
17.2.1.2.2.1 Method 1: From 3-(Aryldiazenyl)-2,1-benzisoxazoles ................... 293
17.2.1.2.2.2 Method 2: From Annulated Pyrazol-N-amines ......................... 293
17.2.1.2.2.3 Method 3: From Annulated 1,2,3-Triazolium-1-arylimides .............. 295
17.2.1.2.2.4 Method 4: From Imidazo[4,5-d][1,2,3]thiadiazin-4-imines .............. 296
17.2.1.2.2.5 Method 5: From N-Aminoquinazolin-2-ones and Related Compounds .. 296
17.2.1.2.3 Aromatization ............................................................ 297
17.2.1.2.4 Synthesis by Substituent Modification ..................................... 298