Highly diastereoselective synthesis of rigid 3-enamino-1,5-benzodiazepines

A variety of new (3-2)-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-2-one. High yields with excellent diastereoselectivity were obtained. The structure of cis-beta-enamino-1,5-benzodiazepine 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. [GRAPHICS] .