BF3·OEt2-mediated cyclization of β,γ-unsaturated oximes and hydrazones with N-(arylthio/arylseleno)succinimides: an efficient approach to synthesize isoxazoles or dihydropyrazoles

Abstract

A highly efficient BF₃·OEt₂-mediated cyclization of β,γ-unsaturated oximes and tosylhydrazones with N-(arylthio/arylseleno)succinimides has been established for the construction of N-heterocycles in a one-step manner. This metal-free cyclization provides direct access to isoxazoles and dihydropyrazoles in good to excellent yields at room temperature. The mechanistic experiments support the formation of a cationic species PhS⁺ which plays a critical role in this cyclization process.