Solution-phase parallel synthesis of 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones

Practical and efficient parallel methods have been developed for the synthesis of 7,8-disubstituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones and 3,7,8-trisubstituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones. This benzothiazepin-4(5H)-one skeleton possesses three or four diversity points. Furthermore, three novel tricycles integrating a benzothiazepin-4(5H)-one scaffold with other privileged structures, such as benzimidazole, benzimidazolone, and thio-benzimidazole, were also developed. The synthetic strategy provides an efficient way to access the benzothiazepinone core, starting from commercially available 1,5-difluoro-2,4-dinitrobenzene (DFDNB), and also allows further derivation of the strategically anchored functionalities.