Download PDF
Synthesis 2005(5): 809-813  
DOI: 10.1055/s-2005-861824
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Alkyl-, Aryl- and Heteroaryl-Substituted 2-[3-Oxo-2,3-dihydro-1H-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines from β-Alkoxyvinyl Trifluoromethyl Ketones

Helio G. Bonacorso*, Demétrius B. Martins, Marcos A. P. Martins, Nilo Zanatta, Alex F. C. Flores
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil
Fax: +55(55)220 8031; e-Mail: heliogb@base.ufsm.br ;
Further Information

Publication History

Received 6 August 2004
Publication Date:
14 February 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

A general method for the synthesis of a novel series of 4-alkyl, 4-aryl, and 4-heteroaryl-substituted 2-[4-(2-hydroxyethyl)-5-methyl-3-oxo-2,3-dihydro-1H-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines, in 35-80% yields, by cyclocondensation of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones with 1-amidino-4-(2-hydroxyethyl)-3-methyl-3-pyrazolin-5-one in the presence of anhydrous potassium carbonate, is described.

Key words

trifluoromethyl ketones - pyrazolylpyrimidines - pyrazolinones - pyrimidines - halogenated heterocycles

    References

  • 1 Khannaa IS. Weier RM. Yu Y. Collins PW. Miyashiro JM. Koboldt CM. Veenhuizen AW. Currie JL. Seibert K. Isakson PC. J. Med. Chem.  1997,  40:  1619 
    CrossrefGoogle Scholar
  • 2 Boehm JC. Smietana JM. Sorenson ME. Garigipati RS. Gallagher TF. Sheldrake PL. Bradbeer J. Badger AM. Laydon TJ. Lee JC. Hillegass LM. Griswold DE. Breton JJ. Chabot-Fletcher MC. Adans JL. J. Med. Chem.  1996,  39:  3929 
    CrossrefGoogle Scholar
  • 3 Li JJ. Anderson GD. Burton EG. Cogburn JN. Collins JT. Garland DJ. Gregory SA. Huang H. Isakson PC. Koboldt CM. Logusch EW. Norton MB. Perkins WE. Reinhard EJ. Seibert K. Veenhuizen AW. Zhang Y. Reitz BD. J. Med. Chem.  1995,  38:  4570 
    CrossrefGoogle Scholar
  • 4a Cullen E. J. Pharm. Sci.  1984,  73:  579 
    CrossrefPubMedGoogle Scholar
  • 4b Buschmann H. Christoph T. Friederichs E. Maul C. Sunfermann B. Chemistry and Pharmacology to Clinical Application   Wiley-VCH; Weinheim: 2002. 
    CrossrefPubMedGoogle Scholar
  • 4c Elguero J. Goya P. Jagerovic N. Silva AMS. Pyrazoles as Drugs: Facts and Fantasies-Targets in Heterocyclic Systems   Vol. 6:  Italian Society of Chemistry; Rome: 2002.  p.52-98  
    CrossrefPubMedGoogle Scholar
  • 5 Oshima Y. Akiamoto T. Tsukada W. Yamaguchi K. Kojima H. Chem. Pharm. Bull.  1969,  17:  1492 
    CrossrefGoogle Scholar
  • 6 Naito T. Yoshikawa T. Kitahara SI. Aoki NE. Chem. Pharm. Bull.  1969,  17:  1467 
    CrossrefGoogle Scholar
  • 7 Ikeda M. Maruyama K. Nobuhara Y. Yamada Y. Okabe S. Chem. Pharm. Bull.  1997,  45:  549 
    Google Scholar
  • 8 Severevicuite V. Garaliene V. Vainilavicius P. Hetzheim A. Pharmazie  1998,  53:  233 
    Google Scholar
  • 9 Shirakawa K. Tsujikawa T. Takeda Kenkysho Nempo  1963,  22:  19 ; Chem. Abstr. 1964, 55, 10450
    Google Scholar
  • 10 Konish K, Kuragano T, and Matsura K. inventors; Jpn. Kokai Tokkyo Koho; JP  6 200 404.  ; Chem. Abstr. 1987, 106, 171125
  • 11 Konish K. Kuragano T. Nippon Noyaku Gakkaishi  1990,  13 ; Chem. Abstr. 1990, 113, 36297
    Google Scholar
  • 12 Naito T, Oshima Y, Yoshikawa T, Kasahara A, Domori R, Nakai Y, and Tsukada WS. inventors; African Pat.  6704936.  ; Chem. Abstr. 1969, 70, 57876
  • 13 Joule JA. Smith GF. Heterocyclic Chemistry   Van Nostrand; London: 1972. 
    Google Scholar
  • 14 Badawey El.-SAM. J. Heterocycl. Chem.  1996,  33:  226 
    Google Scholar
  • 15a Martins MAP. Flores AFC. Bastos GP. Zanatta N. Bonacorso HG. J. Heterocycl. Chem.  1999,  36:  837 
    CrossrefGoogle Scholar
  • 15b Martins MAP. Sinhorin AP. Zimmermann NEK. Zanatta N. Bonacorso HG. Bastos GP. Synthesis  2001,  1959 
    CrossrefGoogle Scholar
  • 15c Martins MAP. Sinhorin AP. Zimmermann NEK. Rosa A. Zanatta N. Bonacorso HG. Bastos GP. Neto M. Synth. Commum.  2002,  32:  425 
    CrossrefGoogle Scholar
  • 15d Martins MAP. Pereira CMP. Zimmermann NEK. Moura S. Sinhorin AP. Cúnico W. Zanatta N. Bonacorso HG. Flores ACF. Synthesis  2003,  2353 
    CrossrefGoogle Scholar
  • 15e Martins MAP. Bastos GP. Sinhorim AP. Zimmermann NEK. Rosa A. Brondani S. Emmerich D. Bonacorso HG. Zanatta N. J. Fluorine Chem.  2003,  123:  249 
    CrossrefGoogle Scholar
  • 15f Martins MAP. Pereira CMP. Zimmermann NEK. Cúnico W. Moura S. Beck P. Zanatta N. Bonacorso HG. J. Fluorine Chem.  2003,  123:  261 
    CrossrefGoogle Scholar
  • 15g Martins MAP. Flores AFC. Bastos GP. Sinhorin A. Bonacorso HG. Zanatta N. Tetrahedron Lett.  2000,  41:  293 
    CrossrefGoogle Scholar
  • 16a Martins MAP. Freitag R. Flores AFC. Zanatta N. J. Heterocycl. Chem.  1995,  32:  1491 
    CrossrefGoogle Scholar
  • 16b Bonacorso HG. Oliveira MR. Wentz AP. Oliveira AB. Hörner M. Zanatta N. Martins MAP. Tetrahedron  1999,  55:  345 
    CrossrefGoogle Scholar
  • 16c Flores AFC. Martins MAP. Rosa A. Flores DC. Zanatta N. Bonacorso HG. Synth. Commun.  2002,  32:  1585 
    CrossrefGoogle Scholar
  • 16d Bonacorso HG. Lewandowski H. Drekener RL. Costa MB. Pereira CMP. Wastowski AD. Peppe C. Martins MAP. Zanatta N. J. Fluorine Chem.  2003,  122:  159 
    CrossrefGoogle Scholar
  • 16e Martins MAP. Pereira CMP. Beck P. Machado P. Moura S. Teixeira MVM. Bonacorso HG. Zanatta N. Tetrahedron Lett.  2003,  44:  6669 
    CrossrefGoogle Scholar
  • 16f Bonacorso HG. Wastowski AD. Zanatta N. Martins MAP. Naue JA. J. Fluorine Chem.  1998,  92:  23 
    CrossrefGoogle Scholar
  • 17a Pacholski IL. Blanco I. Zanatta N. Martins MAP. J. Braz. Chem. Soc.  1992,  2:  118 ; Chem. Abstr. 1994, 120, 323443
    CrossrefGoogle Scholar
  • 17b Zanatta N. Madruga CC. Marisco PC. Flores DC. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  2000,  37:  1213 
    CrossrefGoogle Scholar
  • 17c Zanatta N. Cortelini MF. Carpes MJS. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  1997,  34:  509 
    CrossrefGoogle Scholar
  • 17d Zanatta N. Fagundes M. Hellensohn R. Martins MAP. Bonacorso HG. J. Heterocycl. Chem.  1998,  35:  451 
    CrossrefGoogle Scholar
  • 17e Bonacorso HG. Lopes IS. Wastowski AD. Zanatta N. Martins MAP. J. Fluorine Chem.  2003,  120:  29 
    CrossrefGoogle Scholar
  • 18 Zanatta N. Barichello R. Bonacorso HG. Martins MAP. Synthesis  1999,  765 
    Article in Thieme ConnectGoogle Scholar
  • 19a Zanatta N. Rosa LS. Loro E. Bonacorso HG. Martins MAP. J. Fluorine Chem.  2001,  107:  149 
    Article in Thieme ConnectGoogle Scholar
  • 19b Zanatta N. Rosa LS. Cortelini MFM. Beux S. Santos APD. Bonacorso HG. Martins MPA. Synthesis  2002,  2404 
    Article in Thieme ConnectGoogle Scholar
  • 20a Bonacorso HG. Bittencourt SRT. Wastowski AD. Wentz AP. Zanatta N. Martins MAP. Tetrahedron Lett.  1996,  37:  9155 
    CrossrefGoogle Scholar
  • 20b Bonacorso HG. Bittencourt SRT. Wastowski AD. Wentz AP. Zanatta N. Martins MAP. J. Heterocycl. Chem.  1999,  36:  45 
    CrossrefGoogle Scholar
  • 20c Bonacorso HG. Marques LLM. Zanatta N. Martins MAP. Synth. Commun.  2002,  32:  3225 
    CrossrefGoogle Scholar
  • 21a Bonacorso HG. Muniz MN. Wastowski AD. Zanatta N. Martins MAP. Heteroat. Chem.  2003,  14:  132 
    CrossrefGoogle Scholar
  • 21b Bonacorso HG. Lourega RV. Wastowski AD. Flores AFC. Zanatta N. Martins MAP. Tetrahedron Lett.  2002,  43:  9315 
    CrossrefGoogle Scholar
  • 21c Bonacorso HG. Wastowski AD. Muniz MN. Zanatta N. Martins MAP. Synthesis  2002,  1079 
    CrossrefGoogle Scholar
  • 21d Flores AFC. Brondani S. Zanatta N. Rosa A. Martins MAP. Tetrahedron Lett.  2002,  43:  8701 
    CrossrefGoogle Scholar
  • 22 Bonacorso HG. Wentz AP. Zanatta N. Martins MAP. Synthesis  2001,  1505 
    Article in Thieme ConnectGoogle Scholar
  • 23 Zanatta N. Flores DC. Madruga CC. Faoro D. Flores AFC. Bonacorso HG. Martins MAP. Synthesis  2003,  894 
    Article in Thieme ConnectGoogle Scholar
  • 24 Badawey El.-SAM. El-Ashmawey IM. Eur. J. Med. Chem.  1998,  33:  349 
    Google Scholar
  • 25 Inouye K. Tezuka K. Takeda W. Sugai S. J. Fluorine Chem.  1987,  35:  275 
    CrossrefGoogle Scholar
  • 26a Colla A. Martins MAP. Clar G. Krimmer S. Fischer P. Synthesis  1991,  483 
    CrossrefGoogle Scholar
  • 26b Siqueira GM. Flores AFC. Clar G. Zanatta N. Martins MAP. Química Nova  1994,  17:  24 ; Chem. Abstr. 1995, 122, 187063
    CrossrefGoogle Scholar
  • 26c Bonacorso HG. Martins MAP. Bittencourt S. Lourega RV. Zanatta N. Flores AFC. J. Fluorine Chem.  1999,  99:  177 
    CrossrefGoogle Scholar