Phosphorus, Sulfur and Silicon and the Related Elements p. 1143 - 1155 (2003)
Update date:2022-09-26
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El Massry
Reaction of phenylpyruvic acid with semicarbazide afforded 6-benzyl-2H-[1,2,4]triazine-3,5-dione (1) which upon oxidation with potassium dichromate furnished 6-benzoyl-2H-[1,2,4]triazine-3,5-dione (2) in good yield. Constructing pyrazolo[3,4-e][1,2,4] triazine system (4) was achieved by reacting 2 with arylhydrazines in ethanolic solution. However treatment of 2 with the less reactive heteroarylhydrazines gave only the corresponding hydrazones (3). Attempt for constructing 1,2,4,5,10-pentaaza-dibenzo[a,d]cyclohept-3-one (7) from 2 was failed and (benzoimidazol-2-yl) [1,2,4] triazine derivative (6) was the only product. Reaction of 1 with phosphorus pentasulphide afforded compounds 8 and 9. Compound 8 was transformed to the hydrazino compound 14, which led to the construction of triazolo[4,3-d] [1,2,4]triazine system. Thus compounds 15 and 16 were obtained by reacting 14 with carbon disulfide or acetic anhydride respectively. Attempt to couple 8 with chloroacetic acid failed, while it's known isomer 10 led to the formation of thiazolo [2,3-c] [1,2,4]triazine derivative (13). Simple theoretical calculation using AM1 and PM3 semiempirical Hamitonian provided rational ways to correlate the reactivity with structure proposed.
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Doi:10.1007/BF00973419
()Doi:10.1016/S0040-4039(03)01811-2
(2003)Doi:10.1021/ma034425s
(2003)Doi:10.1021/ja01174a528
(1949)Doi:10.1081/SCC-120021503
(2003)Doi:10.1016/j.ica.2014.07.009
(2014)