Design, synthesis, and antimicrobial activity evaluation of new compounds containing five and seven-membered heteroaromatic systems is the main task of the present paper. The target compounds: 2,2'- (benzene-1,4-diyl) bis{3-[(7-methyl-5-(4-substituted phenyl)[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazepine]amino-2-methyl-[1,2-e][1,3]-benzoxazepine-4,7-dione)} (4a-d) and 2,2'-(benzene-1,4-diyl)bis{1(H)-3-[(7-methyl-5-(4-substituted phenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine]amino-2-methyl-[1,2-e][1,3]-benzodiazepine-4,7-dione)} (5a-d) were synthesized by cycloaddition reaction between phthalic anhydride and phthalimide with various derivatives of [1,2,4]triazolo[3,4-b][1,3,4] thiadiazepine which were previously prepared by the condensation reaction of bis-4-amino-4H-1,2,4-triazole-3-thiol derivatives and 4-substituted benzoylacetone. The newly synthesized compounds were screened as antimicrobial compounds. [GRAPHICS]