The cyclization/rearrangement of α-hydroxy ketones with trifluoromethyl N-acylhydrazones to synthesize multi-substituted trifluoromethyloxazolines

Literature Information

Publication Date 2023-11-09
DOI 10.1039/D3CC03854H
Impact Factor 6.222
Authors

Junjiao Wang, Yongwei Shang, Xiujuan Zhao, Zhenli Cui, Yang Li, Ke-Hu Wang, Danfeng Huang, Yulai Hu, Na Wang, Lei Feng


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Abstract

A highly efficient and metal-free [3+2] cyclization/rearrangement reaction toward the synthesis of multisubstituted trifluoromethyloxazolines from α-hydroxyketones and trifluoromethyl N-acylhydrazones has been developed. The unprecedented rearrangement of the amide fragment under acidic conditions after cleavage of the N–N bond of acylhydrazones has opened up new avenues for the development of reactions involving trifluoromethyl N-acylhydrazones. DFT calculations show that the mechanism involves multiple proton transfer processes.

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