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4-(4-Acetylphenylamino)cycloocteno [4,5]thieno [2,3-d]pyrimidine (4) was prepared and condensed with certain aldehydes, phenylhydrazine, malononitrile to obtain 5a-d, 6 and 7, respectively. 4-Hydrazino & 4-substituted amino derivatives of 2-arylcycloocteno[4,5]thienopyrimidines 10a-c & 11a-i were synthesized. Cyclization of the hydrazino compounds 10a-c with orthoalkanoate esters or the arylidene derivatives 12a-c with bromine in acetic acid afforded the fused triazolo system 13a-i. Reaction of the hydrazino compound 10c with acetic anhydride gave 15 while the reaction of 10b,c with acid chlorides gave 16a-d. Furthermore, the tetrazolothienopyrimidines 17a-c were synthesized. Some of the newly synthesized compounds were tested for their antimicrobial activity.