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Reductive Cyclization of o-Nitrophenyl Propargyl Alcohols: Facile Synthesis of Substituted Quinolines

Matthew J. Sandelier and Philip DeShong*

*Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, Email:

M. J. Sandelier, P. DeShong, Org. Lett., 2007, 9, 3209-3212.

DOI: 10.1021/ol0710921 (free Supporting Information)

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Reduction of secondary and tertiary o-nitrophenyl propargyl alcohols followed by acid-catalyzed Meyer-Schuster rearrangement gave 2-substituted and 2,4-disubstituted quinolines, respectively in good yields.

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proposed mechanism

Key Words

Quinolines, Meyer-Schuster Rearrangement

ID: J54-Y2007-2650