A variety of new (3-Z)-3-((alkyl/aryl)aminomethylene)-4-(2-hydroxyphenyl)-1,3-dihydro-2H-1,5-benzodiazepin-2-ones were synthesized via addition of primary amines on the benzopyrano[4,3-c]-1H-1,5-benzodizepin-2one. High yields with excellent diastereoselectivity were obtained. The structure of cis-β-enamino-1,5benzodiazepine derivatives was characterized by 1D and 2D NMR and confirmed by an X-Ray diffraction analysis. All prepared compounds were evaluated for their in vitro antibacterial activities and promising results were given.

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