CuX(2)介导的不饱和酰胺的氧溴化/氨基氯化反应：亚胺内酯和内酰胺的合成

CuX(2)-mediated oxybromination/aminochlorination of unsaturated amides: synthesis of iminolactones and lactams.

作者信息

Zhang Zhi-Qiang, Liu Feng

机构信息

Jiangsu Key Laboratory of Translational Research and Therapy for Neuro-Psycho-Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China.

出版信息

Org Biomol Chem. 2015 Jun 28;13(24):6690-3. doi: 10.1039/c5ob00520e.

DOI:10.1039/c5ob00520e

PMID:26007699

Abstract

We report herein a CuX2-mediated halocyclization of γ,δ-unsaturated amides for the synthesis of functionalized iminolactones and lactams respectively under mild reaction conditions. Mechanism studies indicated that N-attack cyclization was via a radical route while oxycyclization was via a nucleophilic attack on the activated C=C bond.

摘要

我们在此报告一种由CuX2介导的γ,δ-不饱和酰胺的卤环化反应，该反应可在温和的反应条件下分别用于合成官能化的亚胺内酯和内酰胺。机理研究表明，氮原子进攻的环化反应是通过自由基途径进行的，而氧原子进攻的环化反应是通过对活化的碳碳双键进行亲核进攻来实现的。