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

Guo-Lin Gao, Yan-Ning Niu, Ze-Yi Yan, Hong-Li Wang, Gang-Wei Wang, Ali Shaukat and Yong-Min Liang*

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan, Email: liangymlzu.edu.cn

G.-L. Gao, Y.-N. Niu, Z.-Y. Yan, H.-L. Wang, G.-W. Wang, A. Shaukat, Y.-M. Liang, J. Org. Chem., 2010, 75, 1305-1308.

DOI: 10.1021/jo9026116 (free Supporting Information)


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Abstract

A domino reaction of benzimidoyl chlorides with 1,6-enynes gives quinoline derivatives via palladium-catalyzed Sonogashira coupling and subsequent cyclization. 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.

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Key Words

Quinolines


ID: J42-Y2010-0520