Routes to Pyrazolo[3,4-e][1,4]thiazepine, Pyrazolo[1,5-a]pyrimidine and Pyrazole Derivatives

摘要

5-Aminopyrazole 1 was condensed with aryl aldehydes to give the 4-arylidenes 2. Compound 2 reacted with thioglycolic acid and ethyl cyanoacetate to give the pyrazolothiazepines 3 and pyrazolopyrimidines 4, respectively. Diazotized 2a coupled with resorcinol to give the pyrazole derivative 5a. Reaction of la with beta-keto esters 7, 8 and acetoacetanilides 13 afforded the pyrazolopyrimidines 11,12 and 15, respectively. Condensation of la with2-acetylindan-l,3-dione 16 yielded fused pyrazolopyrimidine 18. Compound la also reacted with the enaminonitriles 19 and 22 to give the pyrazolopyrimidine 20 and 24, respectively.