Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization To Synthesize Quinoline Derivatives

A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed. The procedure is si...

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Bibliographic Details
Published in:Journal of organic chemistry 2010-02, Vol.75 (4), p.1305-1308
Main Authors: Gao, Guo-Lin, Niu, Yan-Ning, Yan, Ze-Yi, Wang, Hong-Li, Wang, Gang-Wei, Shaukat, Ali, Liang, Yong-Min
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Benzamides - chemistry
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Palladium - chemistry
Preparations and properties
Quinolines - chemical synthesis
Quinolines - chemistry
Reactivity and mechanisms
Structure-Activity Relationship
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Summary:A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed. The procedure is simple, rapid, and general, and the substrates are readily available.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9026116