Facile access to 1-aryl-2,3-naphthalimides via consecutive amidation/dehydro-Diels–Alder reactions

Abstract

A facile approach for quick and efficient access to structurally complex 2,3-naphthalimide derivatives is developed. Easily accessible and inexpensive β-arylpropiolic acids and primary amines are used as the reaction starting materials. Both reactants can tolerate a diversity of substituents with various electronic and steric effects. Multi-functional 1-aryl-2,3-naphthalimides are afforded in generally moderate to excellent yields through a consecutive cascade amidation/dehydro-Diels–Alder reaction in one-pot operations. Promising applications of the afforded 1-aryl-2,3-naphthalimide products in bactericide development for plant protections are also exhibited.