Synthesis 2015; 47(21): 3292-3300
DOI: 10.1055/s-0034-1381009
paper
© Georg Thieme Verlag Stuttgart · New York

An Approach to the Synthesis of Pyrimido[b]azepines via Ruthenium-Catalyzed Ring-Closing Metathesis

Authors

  • Tong-Bo Zhang

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Quan-Zhi Yang

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Yuan-Yuan Cao

    b   Taihe Hospital Affiliated with Hubei University of Medicine, Shiyan 442000, Hubei, P. R. of China
  • Shao-Tong Wu

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Yu Zhang

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Ying Guo

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Jian-Xiong Zhao

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Xue-Feng Sun

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Zhi-Li Zhang

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Chao Tian

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
  • Jun-Yi Liu*

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
    c   The State Key Laboratory of National and Biomimetic Drugs, Peking University, Beijing 100191, P. R. of China   Email: jyliu@bjmu.edu.cn
  • Xiao-Wei Wang*

    a   Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China   Email: xiaoweiwang@bjmu.edu.cn
Further Information

Publication History

Received: 29 March 2015

Accepted after revision: 17 May 2015

Publication Date:
24 July 2015 (online)


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Abstract

A highly efficient approach to the synthesis of a series of pyrimido[b]azepines has been developed with 5-allyl-2,4,6-trichloropyrimidine as the starting material in six or seven steps via a ring-closing metathesis (RCM) reaction. The absolute configuration of the key intermediate pyrimido[4,5-b]azepine was ascertained by X-ray crystal structure analysis.