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One-Pot Phosphine-Catalyzed Syntheses of Quinolines

San Khong and Ohyun Kwon*

*Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States, Email: ohyunchem.ucla.edu

S. Khong, O. Kwon, J. Org. Chem., 2012, 77, 8257-8267.

DOI: 10.1021/jo3015825 (free Supporting Information)


Abstract

An efficient one-pot procedure allows the preparation of substituted quinolines from activated acetylenes and o-tosylamidocarbonyl compounds under base-catalyzed, mild conditions. The generation of a β-phosphonium enoate α-vinyl anion in situ is followed by Michael addition of the deprotonated tosylamides and subsequent rapid aldol cyclization. Detosylation of the dihydroquinoline intermediates occurred readily in the presence of aqueous HCl.

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Key Words

quinolines, organocatalysis


ID: J42-Y2012-3080