Chinese Journal of Organic Chemistry >
SOCl2/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes
Received date: 2017-06-15
Revised date: 2017-07-30
Online published: 2017-09-08
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.
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
Zhou Anxi , Zheng Dagui , Zhu Xianhong , Wang Meimei . SOCl2/N-Methyl Pyrrolidone-Mediated Beckmann Rearrangement of Ketoximes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(11) : 2905 -2910 . DOI: 10.6023/cjoc201706020
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