Synthesis and isomerization of thienotriazolopyrimidine and thienotetrazolopyrimidine derivatives with potential anti-inflammatory activity

Abstract

Several derivatives containing the thieno[2,3-d]pyrimidine system were prepared starting from 2-amino-4,5-dihydronaphtho[2,1-b]thiophene-1-carbonitrile (1). In particular, the synthesis and structure characterization of 8,9-dihydronaphtho- [1′,2′:4,5]thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine derivatives 13–16 and their isomerization to 8,9-dihydronaphtho[1′,2′:4,5]thieno[3,2-e][1,2,4]-triazolo[1,5-c]pyrimidine derivatives 17–20 under different suitable reaction conditions were reported and verified with X-ray analysis. Moreover, compounds 13, 14 and 22 were tested as potential anti-inflammatory agents and derivative 14 showed potent activity in carrageenan test. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:226–234, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20114