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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:

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

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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