Novel tricyclic thienopyrimidines (3, 5, 6, 9, 11, 12) and triazole fused tetracyclic thienopyrimidines (4a-c, 10a-c) were synthesized from precursors 2-amino-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile 1 and 2-amino-7-oxo-4,5,6,7-tetrahydro-1-benzothio-phene-3-carbonitrile 7 respectively. The corresponding precursors were prepared by employing the Gewald reaction. The structures of newly synthesized compounds were characterized by spectral and analytical data. All the compounds were screened for their biological activities. Some of the compounds displayed promising antibacterial and antifungal activities.