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In contrast to target‐oriented synthesis that aims to access precise regions of chemistry, diversity‐oriented synthesis via multicomponent synthesis populates chemical space broadly with small molecules having diverse structures. This study has achieved the diversity‐oriented synthesis of novel imidazo[4′,5′:4,5]benzo[e][1,4]thiazepinones (4) and benzo[d]imidazolyl thiazolidinones (5) controlled by the nature of substitution effect of the reaction component. The one‐pot reaction of benzimidazole 1, aromatic aldehyde 2, and mercaptoacetic acid 3 leads to the formation of imidazo[4′,5′:4,5]benzo[e][1,4]thiazepinones (4) with electron‐donating groups as substitution on aromatic aldehyde while electron‐withdrawing substitutions produced benzo[d]imidazolyl thiazolidinones (5). The title compounds (4) and (5) were evaluated for their antimicrobial and anti‐inflammatory activities.