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Synthesis 2010(10): 1678-1686  
DOI: 10.1055/s-0029-1218701
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Friedländer Quinoline Synthesis: Scope and Limitations

An-Hu Li*, David J. Beard, Heather Coate, Ayako Honda, Mridula Kadalbajoo, Andrew Kleinberg, Radoslaw Laufer, Kristen M. Mulvihill, Anthony Nigro, Pawan Rastogi, Dan Sherman, Kam W. Siu, Arno G. Steinig, Ti Wang, Doug Werner, Andrew P. Crew, Mark J. Mulvihill
Department of Cancer Chemistry, OSI Pharmaceuticals, Inc., 1 Bioscience Park Drive, Farmingdale, NY 11735, USA
Fax: +1(631)8455671; e-Mail: ali@osip.com;
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Publication History

Received 4 January 2010
Publication Date:
12 March 2010 (online)

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Abstract

A highly effective one-pot Friedländer quinoline synthesis from o-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The o-nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono- or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%).

Key words

quinolines - condensation - heterocycles - aldehydes - ketones­

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