A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

Russell J. Johnson; Donogh J. R. O'Mahony; William T. Edwards; Matthew A. J. Duncton

doi:10.1039/C2OB27113C

A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

Russell J. Johnson,^a Donogh J. R. O'Mahony,*^a William T. Edwards^a and Matthew A. J. Duncton*^a

* Corresponding authors

^a Renovis, Inc. (a wholly-owned subsidiary of Evotec AG), Two Corporate Drive, South San Francisco, USA
E-mail: djromahony@yahoo.com, mattduncton@yahoo.com
Tel: +1 917-345-3183

Abstract

5,6,7,8-Tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines with appended trifluoromethyl groups are valuable chemotypes in medicinal chemistry due to the presence of a partially-saturated bicyclic ring and metabolically-stable CF₃ group. ¹H NMR studies were used to optimize the preparation of such compounds, using a three-step/one-pot procedure, to provide novel 2,6-disubstitued derivatives with a tertiary-substituent. Racemic 2,6-disubstituted tetrahydroquinolines were separated by chiral HPLC to provide single enantiomers.

Supplementary files

Publication details

The article was received on 30 Oct 2012, accepted on 14 Dec 2012 and first published on 16 Jan 2013

Article type: Paper

DOI: 10.1039/C2OB27113C

Citation: Org. Biomol. Chem., 2013,11, 1358-1366

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A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

R. J. Johnson, D. J. R. O'Mahony, W. T. Edwards and M. A. J. Duncton, Org. Biomol. Chem., 2013, 11, 1358
DOI: 10.1039/C2OB27113C
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Organic & Biomolecular Chemistry

A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

Abstract

Supplementary files

Publication details

A concise one-pot synthesis of trifluoromethyl-containing 2,6-disubstituted 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydronaphthyridines

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