Highly Regioselective Friedländer 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_mcwilliams
merck.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
see article for more reactions
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.
see article for more examples
Key Words
Friedlaender Quinoline Synthesis, 1,8-naphthyridines, quinolines
ID: J42-Y2003-200
