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Synthesis 2011(7): 1149-1156  
DOI: 10.1055/s-0030-1258448
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Catalytic Hydrogenation of 3-Amino-6-(trifluoromethyl)-5,6-dihydropyridin-2(1H)-ones and Its Use in the Synthesis of Trifluoromethyl-Containing Mimetics of Ornithine and Thalidomide

Nataliya A. Tolmachovaa, Violetta G. Dolovanyuka, Igor I. Gerusa, Ivan S. Kondratova, Vitaliy V. Polovinkob, Klaus Berganderc, Günter Haufe*c
a Institute of Bioorganic Chemistry and Petrochemistry, National Ukrainian Academy of Science, Murmanska 1, Kiev 94 02660, Ukraine
b Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
c Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
Further Information

Publication History

Received 8 December 2010
Publication Date:
01 March 2011 (online)

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Abstract

A series of 3-amino-6-(trifluoromethyl)-5,6-dihydropyridin-2(1H)-ones and 6-hydroxy-5,6-dihydropyridin-2(1H)-ones were hydrogenated to give the corresponding piperidinones. These lactams were used for the synthesis of novel trifluoromethyl-containing ornithine analogues and thalidomide mimetics.

Key words

amino acids - catalysis - halides - heterocycles - hydrogenation - piperidinones

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Crystallographic data for compounds cis-10a and cis-2a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 756799 and CCDC 798421, respectively; copies can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or email: deposit@ccdc.cam.ac.uk].