Synthesis of Some New Pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4[3H]-ones and Pyrido[3',2':4,5]thieno[2,3-e]-1,2,4-triazolo[1,5-c]pyrimidine Derivatives

摘要

2,3-Disubstituted-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-one 8a-8c, 9a-9c were obtained by treatment of pyrido[3',2':4,5]thieno[3,2-d][1,3]oxazin-4(3H)-one derivative 3, 3-diacetylamino-thieno[2,3-b]pyridine derivative 5 and 3-ethoxymethyleneaminothieno[1,3-b]pyridine derivative 7a with appropriate amines, respectively. Condensation of compounds 8b, 9b with appropriate #alpha#-chlorocarbonyl compounds gave the corresponding 3-substituted carbonylmethylene-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivative 13a-d. 3-N-Substituted-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-ones 15a,b, 16a,b and 18a,b were also obtained by cyclization of carbohydrazide 14 with different reagents under a variety of conditions. On the other hand, cyclization of 3-amino-4-imino-pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-ones 21a,b with appropriate orthoesters afforded the corresponding 3,5-dialkyl-pyrido[3',2':4,5]thieno[2,3-e]-1,2,4-triazolo[1,5-c]pyrimidines 22a-f.