SOCl2/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes

doi:10.6023/cjoc201706020

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2905-2910.DOI: 10.6023/cjoc201706020 Previous Articles Next Articles

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SOCl₂/N-甲基吡咯烷酮促进的酮肟Beckmann重排

周安西, 郑大贵, 祝显虹, 王媚媚

上饶师范学院江西省普通高校应用有机化学重点实验室上饶 334001

收稿日期:2017-06-15 修回日期:2017-07-30 发布日期:2017-09-08
通讯作者: 周安西 E-mail:zhouanxi@hotmail.com
基金资助:
江西省教育厅科学技术研究（Nos.GJJ161059，GJJ151062）、信江英才866工程领军人才培养计划（No.2013-37）和上饶师范学院科技资助项目.

SOCl₂/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes

Zhou Anxi, Zheng Dagui, Zhu Xianhong, Wang Meimei

Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province, Shangrao Normal University, Shangrao 334001

Received:2017-06-15 Revised:2017-07-30 Published:2017-09-08
Contact: 10.6023/cjoc201706020 E-mail:zhouanxi@hotmail.com
Supported by:
Project supported by the Science and Technology Research Projects of the Education Department of Jiangxi Province (Nos. GJJ161059, GJJ151062), the Xinjiang 866 Project of Excellence Talent (No. 2013-37) and the Science and Technology Projects of Shangrao Normal University.

1. SOCl₂/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes.PDF(3922KB)

Abstract

A mild, convenient, and economical approach for the construction of amides and lactams from ketoximes via Beckmann rearrangement by using a new type of Vilsmeier reagents generated in situ from thionyl chloride and 1-methyl-pyrrolidin-2-one was reported. Various amides and lactams bearing different substituents were obtained in good to excellent yields under mild conditions, and the gram scale reaction was achieved without the loss of the yield. Moreover, it can be used in the synthesis of 2-methylbenzoxazole from 1-(2-hydroxyphenyl)ethanone oxime.

Key words: Beckmann rearrangement, vilsmeier reagent, ketoximes, amides

Cite this article

Zhou Anxi, Zheng Dagui, Zhu Xianhong, Wang Meimei. SOCl₂/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes[J]. Chin. J. Org. Chem., 2017, 37(11): 2905-2910.

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SOCl₂/N-甲基吡咯烷酮促进的酮肟Beckmann重排

SOCl₂/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes

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SOCl2/N-甲基吡咯烷酮促进的酮肟Beckmann重排