A Facile Synthesis of Pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine and Pyrido[2′,3′:3,4]pyrazolo[5,1-c][1,2,4]triazine Bearing a Thiophene Moiety
Pyridinone derivative8was synthesized and transformed into the respective chloropyridine9, which was allowed to react with hydrazine hydrate to afford pyrazolo[3,4-b]pyridin-3-amine derivative11. Compound11was used as a key intermediate for a facile synthesis of the title compounds14,15,17,21a,b, and24a–cwhere the reaction of11with some 1,3-dielecrophiles resulted in the formation of pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines14,15, and17, whereas diazotization of compound11gave the respective diazonium salt18which was coupled with some active methylene-containing compounds to give the corresponding hydrazones19a,band22a–c. Cyclization of the latter hydrazones yielded the pyrido[2′,3′:3,4]pyrazolo[5,1-c][1,2,4]triazines21a,band24a–c, respectively.