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Highly Regioselective Friedlšnder Annulations with Unmodified Ketones Employing Novel Amine Catalysts: Syntheses of 2-Substituted Quinolines, 1,8-Naphthyridines, and Related Heterocycles

Peter G. Dormer, Kan K. Eng, Roger N. Farr, Guy R. Humphrey, J. Christopher McWilliams*, P. J. Reider, Jess W. Sager and R. P. Volante

Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, Email: chris_mcwilliamsmerck.com

P. G. Dormer, K. K. Eng, R. N. Farr, G. H. Humphrey, J. C. McWilliams, P. J. Reider, J. W. Sager, R. P. Volante, J. Org. Chem., 2003, 68, 467-477.

DOI: 10.1021/jo026203i (free Supporting Information)


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Abstract

TABO (1,3,3-trimethyl-6-azabicyclo[3.2.1]octane) is a a highly reactive and regioselective catalyst for the preparation of 2-substituted quinolines, 1,8-naphthyridines, and chromone derivatives from unmodified methyl ketones and o-aminoaromatic aldehydes. Regioselectivity increased with slow addition of the methyl ketone substrate to the reaction mixture.

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Key Words

Friedlaender Quinoline Synthesis, 1,8-naphthyridines, quinolines


ID: J42-Y2003-200