Copper-Catalyzed C-H Alkynylation/Intramolecular Cyclization Cascade for the First Synthesis of Trifluoromethylated Pyrrolo[1,2-a]quinolines

A highly efficient and simple route for the first synthesis of CF3‐substututed pyrrolo[1,2‐a]quinolines from quinolines, terminal alkynes, and methyl 4,4,4‐trifluorobut‐2‐ynoate is reported. The noteworthy feature of this report is that the method involves a two‐step protocol to synthesize tricyclic...

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Bibliographic Details
Published in:European journal of organic chemistry 2016-06, Vol.2016 (17), p.2959-2965
Main Authors: Xu, Zhiliang, Ni, Fei, Han, Jing, Tao, Lili, Deng, Hongmei, Shao, Min, Chen, Jie, Zhang, Hui, Cao, Weiguo
Format: Article
Language:English
Subjects:
Copper
Cyclization
Fluorine
Homogeneous catalysis
Multicomponent reactions
Nitrogen heterocycles
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Summary:A highly efficient and simple route for the first synthesis of CF3‐substututed pyrrolo[1,2‐a]quinolines from quinolines, terminal alkynes, and methyl 4,4,4‐trifluorobut‐2‐ynoate is reported. The noteworthy feature of this report is that the method involves a two‐step protocol to synthesize tricyclic heterocycles in a one‐pot fashion through CuI‐catalyzed C–H alkynylation for the formation of alkynyl‐substituted 1,2‐dihydroquinolines, followed by a CuII‐assisted intramolecular cyclization under air. This strategy tolerates a wide range of substrates with a variety of functional groups under mild conditions, and gives the products in good to excellent yields. An efficient and simple copper‐catalyzed route for the first synthesis of CF3‐substututed pyrrolo[1,2‐a]quinolines from quinolines, terminal alkynes, and methyl 4,4,4‐trifluorobut‐2‐ynoate is described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600449