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Copper‐Catalyzed C–H Alkynylation/Intramolecular Cyclization Cascade for the First Synthesis of Trifluoromethylated Pyrrolo[1,2‐a]quinolines
Author(s) -
Xu Zhiliang,
Ni Fei,
Han Jing,
Tao Lili,
Deng Hongmei,
Shao Min,
Chen Jie,
Zhang Hui,
Cao Weiguo
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600449
Subject(s) - chemistry , alkynylation , intramolecular force , catalysis , combinatorial chemistry , cascade , tricyclic , stereochemistry , medicinal chemistry , organic chemistry , chromatography
A highly efficient and simple route for the first synthesis of CF 3 ‐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 Cu I ‐catalyzed C–H alkynylation for the formation of alkynyl‐substituted 1,2‐dihydroquinolines, followed by a Cu II ‐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.