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One-Pot Friedlšnder 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, Email: aliosip.com

A.-H. Li, D. J. Beard, H. Coate, A. Honda, M. Kadablbajoo, A. Kleinberg, R. Laufer, K. M. Mulvihill, A. Nigro, P. Rastogi, M. W. Siu, A. G. Steinig, T. Wang, D. Werner, A. P. Crew, M. J. Mulvihill, Synthesis, 2010, 1629-1632.

DOI: 10.1055/s-0029-1218701


Abstract

Reduction of o-nitroarylcarbaldehydes o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid followed by in situ condensation of the resulting amines with ketones or aldehydes (Friedlaender quinoline synthesis) gives mono- or disubstituted quinolines, respectively, in very good yields.

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Key Words

Friedlšnder Quinoline Synthesis, quinolines, condensation, heterocycles, aldehydes, ketones, iron


ID: J66-Y2010-1440