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Synlett 2014; 25(12): 1781-1785
DOI: 10.1055/s-0034-1378265
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of Multisubstituted Tetrahydroquinolines through Aza-Michael/ Michael Addition Catalyzed by Quaternary Ammonium Salt

Li Zhang
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: lpsong@shu.edu.cn
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yajun Li
c   School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, Hubei 430074, P. R. of China
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yafen Yuan
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Bin Zhang
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yuan Gao
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yongming Wu*
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Liping Song*
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: lpsong@shu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 27 February 2014

Accepted after revision: 07 May 2014

Publication Date:
05 June 2014 (online)

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Abstract

Multisubstituted tetrahydroquinolines were obtained in excellent yield from an array of N-[2-(3-oxo-3-phenylprop-1-enyl)phenyl]benzamide derivatives in a reaction catalyzed by quaternary ammonium salt. This method provides an efficient approach to the synthesis of densely substituted tetrahydroquinoline derivatives.

Key words

quaternary ammonium salt - tetrahydroquinolines - ­Michael addition - heterocycles

Supporting Information

    for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
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