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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

    References

  • For some recent examples, see:
  • 1a Boeglin D. Hamdan FF. Melendez RE. Cluzeau J. Laperriere A. Héroux M. Bouvier M. Lubell WD. J. Med. Chem.  2007,  50:  1401 
    Search in Google Scholar
  • 1b Manzoni L. Bassanini M. Belvisi L. Motto I. Scolastico C. Castorina M. Pisano C. Eur. J. Org. Chem.  2007,  1309 
  • 1c Smallheer JM. Wang S. Laws ML. Nakajima S. Hu Z. Han W. Jacobson I. Luettgen JM. Rossi KA. Rendina AR. Knabb RM. Wexler RR. Lam PYS. Quan ML. Bioorg. Med. Chem. Lett.  2008,  18:  2428 
    Search in Google Scholar
  • 1d Mezo AR. McDonnell KA. Castro A. Fraley C. Bioorg. Med. Chem.  2008,  16:  6394 
    Search in Google Scholar
  • 1e Lewis JA. Daniels RN. Lindsley CW. Org. Lett.  2008,  10:  4545 
    Search in Google Scholar
  • 2a Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications   Wiley-VCH; Weinheim: 2004. 
  • 2b Uneyama K. Organofluorine Chemistry   Blackwell; Oxford: 2006. 
  • 3a Bégué J.-P. Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine   John Wiley; Hoboken: 2008.  p.365 
  • 3b Fluorine in Medicinal Chemistry and Chemical Biology   Ojima I. Wiley; Chichester: 2009. 
  • 3c Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications   Petrov VA. John Wiley; Hoboken: 2009.  p.399-507  
  • 3d Theodoridis G. Adv. Fluorine Sci.  2006,  2:  121 
    Search in Google Scholar
  • 4 Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis   Wiley-Interscience; New York: 2001.  p.511-513  
  • For some recent examples, see:
  • 5a Shi G.-F. Li J.-Q. Jiang X.-P. Cheng Y. Tetrahedron  2008,  64:  5005 
    Search in Google Scholar
  • 5b Jiang X.-P. Cheng Y. Shi G.-F. Kang Z.-M. J. Org. Chem.  2007,  72:  2212 
    Search in Google Scholar
  • 5c Padwa A. Heidelbaugh TM. Kuethe JT. J. Org. Chem.  2000,  65:  2368 
    Search in Google Scholar
  • For some recent examples, see:
  • 6a Liang G.-B. Qian X. Biftu T. Singh S. Gao Y.-D. Scapin G. Patel S. Leiting B. Patel R. Wu J. Zhang X. Thornberry NA. Weber AE. Bioorg. Med. Chem. Lett.  2008,  18:  3706 
    Search in Google Scholar
  • 6b McCarthy AR. Hartmann RW. Abell AD. Bioorg. Med. Chem. Lett.  2007,  17:  3603 
    Search in Google Scholar
  • 6c Guthikonda RN. Shah SK. Pacholok SG. Humes JL. Mumford RA. Grant SK. Chabin RM. Green BG. Tsou N. Ball R. Fletcher DS. Luell S. MacIntyre DE. MacCoss M. Bioorg. Med. Chem. Lett.  2005,  15:  1997 
    Search in Google Scholar
  • 6d Fischer C, Munoz B, Zultanski S, Methot J, Zhou H, and Brown WC. inventors; WO  2008156580.  ; Chem Abstr. 2008, 150, 77691
  • 7 Tolmacheva NA. Gerus II. Dolovanyuk VG. Kondratov IS. Haufe G. Eur. J. Org. Chem.  2009,  5012 
  • 8 Gerus II. Tolmachova NA. Vdovenko SI. Fröhlich R. Haufe G. Synthesis  2005,  1269 
    Thieme Connect
  • 10a Molteni M. Pesenti C. Sani M. Volonterio A. Zanda M. J. Fluorine Chem.  2004,  125:  1735 
    Search in Google Scholar
  • 10b Bigotti S. Meille SV. Volonterio A. Zanda M. J. Fluorine Chem.  2008,  129:  767 
    Search in Google Scholar
  • 10c Molteni M. Bellucci MC. Bigotti S. Mazzini S. Volonterio A. Zanda M. Org. Biomol. Chem.  2009,  7:  2286 
    Search in Google Scholar
  • 10d Black WC. Bayly CI. Davis DE. Desmarais S. Falgueyret J.-P. Leger S. Li CS. Masse F. McKay DJ. Palmer JT. Percival MD. Robichaud J. Tsoub N. Zambonia R. Bioorg. Med. Chem. Lett.  2005,  15:  4741 
    Search in Google Scholar
  • 10e Li CS. Deschenes D. Desmarais S. Falgueyret J.-P. Gauthier JY. Kimmel DB. Leger S. Masse F. McGrath ME. McKay DJ. Percival MD. Riendeau D. Rodan SB. Therien M. Truong VL. Weslowski G. Zamboni R. Black WC. Bioorg. Med. Chem. Lett.  2006,  16:  1985 
    Search in Google Scholar
  • For recent reviews, see
  • 11a Melchert M. List A. Int. J. Biochem. Cell Biol.  2007,  39:  1489 
    Search in Google Scholar
  • 11b Huang Y.-T. Hsu CW. Chiu TH. Tzu Chi Med. J.  2008,  20:  188 
    Search in Google Scholar
  • 12 Weiss J. Weiss T. Handbook of Ion Chromatography   3rd ed.:  Wiley-VCH; Weinheim: 2004. 
    Search in Google Scholar
9

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].