Synthesis 2005(8): 1269-1278  
DOI: 10.1055/s-2005-865290
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis and Chemical Properties of 3-Acylamino-6-poly­fluoroalkyl-2H-pyran-2-ones

Igor I. Gerus*a, Nataliya A. Tolmachovaa, Sergey I. Vdovenkoa, Roland Fröhlichb, Günter Haufe*b
a Institute of Bioorganic Chemistry and Petrochemistry NASU, Murmanska 1, 02094 Kiev, Ukraine
Fax: +38(44)5732552; e-Mail: igerus@hotmail.com;
b Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
Weitere Informationen

Publikationsverlauf

Received 10 November 2004
Publikationsdatum:
07. April 2005 (online)

Abstract

A number of 3-acylamino-6-polyfluoroalkyl-2H-pyran-2-ones 3 were synthesized from β-alkoxyvinyl polyfluoroalkyl ketones 1 and N-acylglycines 2 in acetic anhydride in high yield. The reactions of trifluoromethyl-containing 2H-pyran-2-one 3b with O- and N-nucleophiles were studied and 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyran-2-one (13), 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyridin-2-one (14a), and N- and O-substituted 3-(N-benzoylamino)-6-trifluoromethyl-2H-pyridin-2-ones (15c,e, and 16) were synthesized.

    References

  • 1a Almtorp GT. Hazell AC. Torssell KBG. Phytochemistry  1991,  30:  2753 
  • 1b Rebuffat S. Davoust D. Molho L. Molho D. Phytochemistry  1980,  19:  427 
  • 1c Juliawaty LD. Watanabe Y. Kitajima M. Achmad SA. Takayama H. Aimi N. Tetrahedron Lett.  2002,  48:  8657 
  • 2a Deck LM. Baca ML. Salas SL. Hunsaker LA. van der Jagt DL. J. Med. Chem.  1999,  42:  4250 
  • 2b Hagen SE. Vara Prasad JVN. Boyer FE. Domagala JM. Ellsworth EL. Gajda C. Hamilton HW. Markoski LJ. Steinbaugh BA. Tait BD. Lunney EA. Tummino PJ. Ferguson D. Hupe D. Nouhan C. Gracheck SJ. Saunders JM. van der Roest S. J. Med. Chem.  1997,  40:  3707 
  • 2c Romero DL. Manninen PR. Han F. Romero AG. J. Org. Chem.  1999,  64:  4980 
  • 2d Hatch MS. Brown WM. Deck JA. Hunsaker LA. Deck LM. van der Jagt DL. Biochim. Biophys. Acta  2002,  1596:  381 
  • 3a Boulanger WA. Katzenellenbogen JA. J. Med. Chem.  1986,  29:  1159 
  • 3b Yamaguchi M, Ito Y, Shibayama A, Yamaji Y, Hanai R, Uotsu S, and Sadohara H. inventors; PCT Int. Appl. WO  9728127.  ; Chem. Abstr. 1997, 127, 190757
  • 3c German LS. Sterlin SR. Cherstkov VF. Izv. Akad. Nauk SSSR, Ser. Khim.  1982,  1657 ; Chem. Abstr. 1982, 97, 162758
  • 4a Whitney JG. Gregory WA. Kauer JC. Roland JR. Snyder JA. Benson RE. Hermann EC. J. Med. Chem.  1970,  13:  254 
  • 4b Walter GA, and Whitney JG. inventors; U.S. Pat. Appl. US  3414615.  ; Chem. Abstr. 1969, 70, 57294
  • 5 Afarinkia K. Vinader V. Nelson TD. Posner GH. Tetrahedron  199,  48:  9111 
  • 6 Ram VJ. Srivastava P. Agarwal N. Sharon A. Maulik PR. J. Chem. Soc., Perkin Trans. 1  2001,  1953 
  • 7 Filler R. Kobayashi Y. Yagupolskii LM. Organo-fluorine Compounds in Medicinal Chemistry and Biochemical Applications   Elsevier; Amsterdam: 1993. 
  • 8a Bu’Lock JD. Smith HG. J. Chem. Soc.  1960,  502 
  • 8b Harris TM. Harris CM. J. Org. Chem.  1966,  31:  1033 
  • 8c Cernigoj-Marzi A. Polanc S. Kočevar M. J. Heterocycl. Chem.  1997,  34:  1753 
  • 9 Gerus II. Gorbunova MG. Kukhar VP. J. Fluorine Chem.  1994,  69:  195 
  • 10 Gorbunova MG. Gerus II. Kukhar VP. Synthesis  2000,  738 
  • 11 Gerus II. Vdovenko SI. Gorbunova MG. Kukhar VP. Khim. Geterosikl. Soedin.  1991,  502 ; Chem. Abstr. 1991, 115: 1832349
  • 12 Kacharova LM. Gerus II. Kacharov AD. J. Fluorine Chem.  2002,  117:  193 
  • 13 Gerus II. Gorbunova MG. Vdovenko SI. Yagupolskii YuL. Kukhar VP. Zh. Org. Khim.  1990,  26:  1877 ; Chem. Abstr. 1991, 115: 8196g
  • 14 Zhu SZ. Wang YL. Peng WM. Song LP. Jin GF. Curr. Org. Chem.  2002,  6:  1057 
  • 15 Kepe V. Kočevar M. Polanc S. Verček B. Tiler M. Tetrahedron  1990,  46:  2081 
  • 16a Kepe V. Polanc S. Kočevar M. Heterocycles  1998,  48:  671 
  • 16b El-Taweel FMAA. Elnagdi MH. J. Heterocycl. Chem.  2001,  38:  981 
  • 17 Vogel G. Chem. Ind. (London)  1962,  968:  1829 
  • 18 Brown SM. Bowden MC. Parsons TJ. Mc Neilly P. Fraine PJ. Org. Process Res. Dev.  1997,  1:  370 
  • 19 Castillo S. Ouadahi H. Herault V. Bull. Soc. Chim. Fr.  1982,  257 
  • 20 Reddy ACS. Narsaiah B. Vernkataratnam RV. J. Fluorine Chem.  1996,  78:  21 
  • 21 Pazenok SV. Gerus II. Chaika EA. Yagupolskii LM. J. Org. Chem. USSR (Engl. Transl.)  1989,  25:  1238 
  • 22 Bravo P. Bruche L. Farina A. Gerus II. Kolycheva MT. Kukhar VP. Meille SV. Viani F. J. Chem. Soc., Perkin Trans. 1  1995,  1667 
  • 23 Palanki MSS. Erdman PE. Gayo-Fung LM. Shevlin GI. Sullivan RW. Suto MJ. Goldman ME. Ransone LJ. Bennett BL. Manning AM. J. Med. Chem.  2000,  43:  3995 
  • 24 Hojo R. Masuda R. Okada E. Synthesis  1990,  347 
  • 25 Vdovenko SI. Gerus II. Gorbunova MG. J. Chem. Soc., Perkin Trans. 2  1993,  559