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Synthesis 2012; 44(12): 1798-1805
DOI: 10.1055/s-0031-1290775
special topic
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C–N Bond Formation

Jun Shao
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66132065   Email: xubin@shu.edu.cn
,
Xiaomei Huang
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66132065   Email: xubin@shu.edu.cn
,
Xiaohu Hong
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66132065   Email: xubin@shu.edu.cn
,
Bingxin Liu
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66132065   Email: xubin@shu.edu.cn
,
Bin Xu*
a   Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China, Fax: +86(21)66132065   Email: xubin@shu.edu.cn
b   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
c   Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, Shanghai 200062, P. R. of China
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Further Information

Publication History

Received: 04 January 2012

Accepted: 01 March 2012

Publication Date:
03 April 2012 (online)

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Abstract

N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route.

Key words

alkynes - amination - cyclization - nitrogen heterocycles - domino reactions

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
  • Supporting Information
 

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