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Electrophile-Driven Regioselective Synthesis of Functionalized Quinolines

Shaukat Ali, Hai-Tao Zhu, Xiao-Feng Xia, Ke-Gong Ji, Yan-Fang Yang, Xian-Rong Song and Yong-Min Liang*

*State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China, Email: liangymlzu.edu.cn

S. Ali, H.-T. Zhu, X.-F. Xia, K.-G. Ji, Y.-F. Yang, X.-R. Song, Y.-M. Liang, Org. Lett., 2011, 13, 2598-2601.

DOI: 10.1021/ol2007154 (free Supporting Information)


Abstract

Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in good yields by a regioselective 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine under mild conditions. The resulting 3-iodoquinolines can be further functionalized by various coupling reactions.


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Key Words

Quinolines


ID: J54-Y2011-1450