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

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
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Publikationsverlauf

Received: 29. März 2015

Accepted after revision: 17. Mai 2015

Publikationsdatum:
24. Juli 2015 (online)


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.