A series of some novel pyrano [2,3-d]pyrimidine 4-10 with 75-95% yields and pyridino[2,3-d]pyrimidine derivatives 11-16 with 75-92% yields is reported. The building structures have been achieved by reaction of 5-arylidene barbituric acid 2 and active nucleophile carbon or nitrogen as examples barbituric acid and acetyl acetone or refluxing of bispyrimidine-2,4,6-trione derivative 3 with cyclizing reagents such as phosphorous pentoxide, hydrazine hydrate and aminothiazole. The newly synthesized structures have been elucidated on the basis of their spectral analysis. Some selected members were screened for antitumor activity. Among the screened compounds 9, 16, 7, 10 and 8 exhibited high antitumor activity.
Reaction of L-tartaric acid with thiocarbohydcrazide afforded (1R, 2S)-1,2-bis(4-amino-5-mercapto-1,2,4-triazol-3-yl)-ethane-1,2-diol (3). The functional groups in 3 allowed the construction of fused heterocycles on the 1,2,4-triazole rings, mainly of the 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine type as in 4, 5, 7, 10, 13 and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole type as in 14.
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