Aminotriazine

In pyrolysis employing molten tin, a flow of the urea on the surface is eventually converted to a sheet of cmde CA 15—20 mm thick. After reaching the edge of the tin bath, the moving sheet falls into a mill. The resultant powdered cmde CA (contaminated with tin metal) is subjected to acid hydrolysis to convert aminotriazines (30—40%) to CA. Tin losses can amount to 15 kg/1 product. 

Derivatives of oxazolofS -eNl ltriazines 620 were prepared (87AJC977) by cyclodehydration of the respective 6-acylaminotriazin-5-ones 619, obtained by acylating 618, with phosphorus oxychloride or phosphorus pentoxide. 6-Phenyloxazolotriazines 620 (R1 = Ph) were also obtained directly when aminotriazinones 618 were heated with benzoic acid anhydride. By a different route, 6-aminotriazin-5-one 618 was con-... 

The reaction of /V-aminotriazines 847 with diaryl carbodiimides led (88H161) directly to the new triazolotriazines 848, which display mesoionic character (Scheme 172). 

A third, not too widely used, approach is transformation of an iV-aminotriazine compound, as shown in Scheme 56. The 3-mercapto-4-amino[l,2,4]triazine derivative 361 was treated with an active methylene ketone and NBS in ethanol to yield the cyclized product 362 in moderate to excellent yield <2001JHC711>. A similar synthetic strategy was also applied in another case <2003KGS1844>. 

Aminotriazines or Iminoe hydrotriazines, CjH4N4, mw 96.09j N 58.31%- The following isomers of these high nitrogen compds are described in the literature ... 

Nitrated and/or Ntinted Aminotriazines were not found in Beil or CA thru 1956... 

Aminotriazines and derivs 1 A267 The vicival or 1,2,3-triazines 9 T353... 

Iminodihydropurine. See Aminopurine A254-L Iminodihydrotriazine. See Aminotriazine A267-L... 

Aminotriazines (37) undergo Curtius rearrangement with diethyl dimorpholinomalonate and thiosemicarbazide to give imidazotriazines (6-azapurines) (38) [95MI1],... 

Mattson RJ, Denhart DJ, Catt JD, et al. Aminotriazine 5-HT7 antagonists. Biooig Med Chem Lett 2004 14 4245-4248. 

Thiazinonium perchlorate 242 also reacts at the 2 position of the heteroring with such 1,3-dinucleophiles as alkylisothioureas and guanidines. After recyclization, alkylmercapto- and aminotriazines 243 were obtained (87MI1) (Scheme 95). 

Catalytic hydrogenation of the TV-oxide (90a) gave 1,2-dihydro-3-amino-l,2,4-triazino[6,5-c]quin-oline (91a) (80%) <73GEP(0)2322418>. Hydrogenation of the TV-oxide (90a) gave the corresponding aminotriazine (47a) <76Mi 717-02). 

A 2 1 mixture of the aminotriazine (145a) and the isomer (146a) was refluxed in the presence of NaOH to give the corresponding triazin-3-ones (131) and (132) in the same ratio <86JHC72i>. 

A mixture of 3-chlorotriazine (149) and the unwanted chlorotriazine (150) could be converted to a mixture of the corresponding 3-aminotriazines (145a) and (146a) in an overall yield of 67% by treatment with a saturated methanolic solution of NH3 the unwanted isomer (146a) was difficult to remove. Subsequent reaction of the 3-aminotriazine (145a) (available pure via a cycloaddition... 

Chlorotriazine (150) could be converted to the corresponding 3-aminotriazine (146a) in a yield of 86% by treatment with a saturated methanolic ammonia solution. Subsequent reaction of the... 

Azine approach. Acylation of the 3-aminotriazine (622) results in cyclocondensation to the corresponding oxadiazole (67CB2585). The facile cyclization is caused by the high activation of the 3-position in a 1,2,4-triazine for nucleophilic substitution. 

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