17th Iranian Seminar of Organic Chemistry , 2010-10-13

Title : ( A general synthesis of new derivatives of pyrimido[4,5-e][1,2,4]triazolo[3,4-b] [1,3,4]thiadiazine )

Authors: Mehdi Bakavoli , Mohammad Rahimizadeh , Ali Keshavarzi , Ali Shiri ,

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Abstract

Some triazolothiadiazines have been reported to possess antibacterial and antifungal activity.[1] Therefore, it seems to be of interest to introduce a pyrimidine ring which has been fused to a triazolothiadiazine ring system. Some pyrimido[4,5-e][1,2,4]-triazolo[3,4- b][1,3,4]-thiadiazine-7,9-diones have been synthesized by the condensation of 3-alkyl-4- amino-5-mercapto-[1,2,4]-triazoles with 5-bromobarbituric acid.[2] In continuation of our previous efforts on the synthesis of new derivatives of pyrimidine fused rings,[3] here, we report the synthesis of new derivatives, namely 7- chloro-3,9-dimethyl-5H-pyrimido[4,5-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (3) from the condensation of 5-bromo-2,4-dichloro-6-methylpyrimidine (1) with 4-amino-3- methyl-4,5-dihydro-1H-1,2,4-triazole-5-thione (2) in CH3CN in alkaline conditions. Then, the resulting product was treated with various secondary amines to give the substituted chlorine atom products 4(a-e) by amines in good to excellent yields.

Keywords

, pyrimido[4, 5-e][1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazine