Synthesis 2020; 52(02): 297-303
DOI: 10.1055/s-0039-1690031
paper
© Georg Thieme Verlag Stuttgart · New York

DMSO-Mediated Synthesis of Methylene-Bridged Unsymmetrical Bisamides in the Presence of AcOH

Authors

  • Yi Zhang §

    a   School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, 310053, P. R. of China
    b   School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. of China   Email: yongmin.ma@tzc.edu.cn   Email: cjmaggie@163.com
  • Dongheng Zhou §

    a   School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, 310053, P. R. of China
  • Yongmin Ma

    a   School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, 310053, P. R. of China
    b   School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000, P. R. of China   Email: yongmin.ma@tzc.edu.cn   Email: cjmaggie@163.com
  • Jing Chen

    a   School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, 310053, P. R. of China

This work was supported by the financial support from Natural Science Foundation of Zhejiang Province (LY19H300001) is gratefully acknowledged.
Further Information

Publication History

Received: 30 July 2019

Accepted after revision: 22 September 2019

Publication Date:
09 October 2019 (online)


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§ These authors contributed equally.

Abstract

A simple and efficient procedure for the synthesis of N-[(methylthio)methyl]benzamides and methylene-bridged unsymmetrical bisamides was achieved mediated by DMSO in the presence of acetic acid. DMSO plays a dual role in the transformation, as not only a solvent, but also an environmentally benign methylene source. The protocol provides new strategies for effective synthesis of unsymmetrical bisamides and avoids the use of transition-metal catalysts.

Supporting Information