Development of methodologies for the regioselective synthesis of four series of regioisomer isoxazoles from b-enamino diketones†

Abstract

Four methodologies are reported for the regioselective synthesis of four series of regioisomer isoxazoles from cyclocondensation of b-enamino diketones and hydroxylamine hydrochloride. Regiochemical control was achieved by varying reaction conditions and substrate structure. The mild reaction conditions used to access 4,5-disubstituted, 3,4-disubtituted, and 3,4,5-trisubstituted regioisomer isoxazoles, as well as the pharmacological and synthetic potential of the products, make these novel methodologies very powerful.