Condensed bridgehead nitrogen heterocyclic systems:: Synthesis, stereochemistry and bioactivity of pyrazolo [3′,4′:4,5] thiazolo [3,2-b]-s-triazoles

A facile synthesis of 2,3-diaryl-6-(p-hydroxyphenyl)-cis-3, 3a-dihydropyrazolo [3', 4':4,5] thiazolo [3,2-b]-s-triazoles 3 has been achieved by the condensation of 3-(phydroxyphenyl)-5-mercapto-s-triazole I with chloroacetic acid and aldehydes in the presence of acetic anhydride, anhyd sodium acetate and gl acetic acid to yield 2(hydroxyphenyl)-6-arylidenethiazolo [3,2-b]-s-triazol-5(6H)-ones 2 followed by treatment with 2,4-dinitrophenylhydrazine. The antibacterial and antifungal activities of some of the compounds have also been evaluated.