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Synthesis 2016; 48(23): 4228-4236
DOI: 10.1055/s-0035-1562624
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Cyclization/Oxidation/Aromatization Cascade: Efficient Synthesis of Trifluoromethylated Pyrrolo[2,1-a]isoquinolines

Lili Tao §
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China, Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Zhiliang Xu §
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China, Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Jing Han
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China, Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Hongmei Deng
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China
,
Min Shao
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China
,
Jie Chen
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China, Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
,
Hui Zhang*
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China, Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
b   Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444, P. R. of China
,
Weiguo Cao*
a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China, Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
d   Key Laboratory of Synthetic Organic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
e   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
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Publication History

Received: 27 June 2015

Accepted after revision: 26 July 2016

Publication Date:
05 September 2016 (online)

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§ These authors contributed equally.

Abstract

An efficient copper-catalyzed synthesis of 3-(trifluoromethyl)pyrrolo[2,1-a]isoquinolines was achieved through a sequential one-pot two-step three-component reaction of a substituted isoquinoline, a terminal aryne, and methyl 4,4,4-trifluorobut-2-ynoate, with air as an oxygen source. This oxidative cyclization proceeds through an initial copper(I)-catalyzed C–H alkynylation to give alkynyl-1,2-dihydroisoquinolines that subsequently undergo a copper(II)-assisted intramolecular cyclization under mild conditions to give the desired products in moderate to excellent yields.

Key words

trifluoromethylation - isoquinolines - copper catalysis - multicomponent reaction - cascade reaction - C–H functionalization

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562624.
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