Synthesis of some new polyfused thienothiophenes Part 4: Synthesis of thienopyrimidine, thienotriazine, thienoimidazotriazine, thienotriazolotriazine, and thienotetrazolotriazine derivatives

摘要

3,4-Diamino-2,5-dicarboxamidothieno(2,3-b)thiophene 1 was allowed to react with CS2, carbonyl compounds, ethyl chloroformate, S,S-acetals and oxallyl chloride to give thienopyrimidines 2-6 and thieno-1,4-diazepine 7. Treatment of compound 1 with nitrous acid afforded compound 8, which converted into the corresponding chloro derivative 9 by using PCl5. Compound 9 was reacted with amino reagents to afford the corresponding thienoimidazotriazines 10 and 11, thienotriazolotriazines 12 and 13 and 4-hydrazinothienotriazine 14. Treatment of compound 14 with aldehydes, triethyl orthoformate, CS2, nitrous acid and ylidenemalononitriles, afforded thienotriazolotriazine 16-18, thienotetrazolotriazine 19, and 4-pyrazolyl-thienotriazine 20-22 derivatives respectively. [References: 20]