Catalyst-free synthesis of isoxazolidine from nitrosoarene and haloalkyne via a 1,2-halo-migration/[3 + 2] cycloaddition cascade

Abstract

An unprecedented catalyst-free three-component reaction to synthesize isoxazolidine from easily accessible haloalkyne, nitrosoarene and maleimide was developed. This reaction was proposed to proceed via a 1,2-halo migration and [3 + 2] cycloaddition cascade, providing a new reaction pattern of alkyne and nitroso containing species wherein a new type of nitrone was generated. Besides, the reaction conditions were efficient and environmentally benign, enabling the formation of various bioactivity-related isoxazolidines.