1,6-Diamino-2-oxo-4-[(10-oxo-4,6,7,8,9,10-hexahydropyrazolo[1,5-a]benzothieno[2,3-d]pyrimidin-3-yl)-1,2-dihydropyridine-3,5-dicarbonitrile (2) reacted with some mono electrophilic reagents such as acetic anhydride, carbon disulfide, chromone-3-carboxylic acid and anthranilic acid to give a novel series of triazolo[1,5-a] pyridines 3-6. Cyclocondensation of compound 6 with carbon disulphide and acetic anhydride afforded pyrido[1,2:2,3]triazolo[1,5-c]quinazolines 7,8. Also, the new pyrido[1,2-b][1,2,4]triazines 9-14 were yielded from interaction of, respectively. The effect of some α,γ-bifunctional electrophiles such as 2 compound 2 reacted with chloroacetyl chloride, oxalyl chloride, sodium pyruvate and/or benzyl -cyano-3,3-bis(methylthio)acrylonitrile, 2-cyano-3,3-bis(methylthio) prop-2-enamide,5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde, chromone-3-carbo-nitrile, 4-chlorobenzylidene malononitrile and/or ethyl 3-(4-chlorophenyl)-2-cyanoprop-2-enoate on compound 2 was also studied and gave some new pyrido[1,2-b][1,2,4]triazipines 15-21. The synthesized compounds were showed a low to high antimicrobial activity towards Gram- positive bacteria, Gram-negative bacteria, yeasts and the fungal strain.