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Synthesis 2001(10): 1505-1508
DOI: 10.1055/s-2001-16087
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regiospecific Cyclization of β-Methoxyvinyl Trifluoromethyl Ketones with Aminoguanidine: A Convenient Method to Obtain Trifluoromethylated 2-[1H-Pyrazol-1-yl]pyrimidines

Helio Gauze Bonacorso*, Alexandre Pereira Wentz, Nilo Zanatta, Marcos Antonio Pinto Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS-Brazil
Fax: +55(55)2208031; e-Mail: heliogb@base.ufsm.br;
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Publication History

Received 10 October 2000
Publication Date:
23 September 2004 (online)

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Abstract

The regiospecific one-pot synthesis of a novel series of 6-alkyl(aryl)-2-[3-alkyl(aryl)-5-trifluoromethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-l-yl]-4-trifluoromethylpyrimidines 2 and 6-alkyl(aryl)-2-[3-alkyl(aryl)-5-trifluoromethyl-1H-pyrazol-l-yl]- 4-trifluoromethylpyrimidines 3 from 4-alkyl(aryl)-1,1,1-trifluoro-4-methoxyalk-3-en-2-ones 1 and aminoguanidine bicarbonate is reported.

Key words

pyrimidines - pyrazoles - 2-(pyrazolyl)pyrimidines - trifluoromethyl vinyl ketones

    References

  • 1 Oshima Y. Akimoto T. Tsukada W. Yamasaki T. Yamaguchi K. Kojima H. Chem. Pharm. Bull.  1969,  17:  1492 
    CrossrefGoogle Scholar
  • 2 Naito T. Yoshikawa T. Kitahara S.-I. Aoki N.-E. Chem. Pharm. Bull.  1969,  17:  1467 
    CrossrefGoogle Scholar
  • 3a Konish K, Kuragano T, and Matsura K. inventors; Jpn. Kokai Tokkyo Koho;  JP 6 200 404. 
  • 4a Konish K. Kuragano T. Nippon Noyaku Gakkaishi  1990,  15:  13 
    Google Scholar
  • 5 Lednicer D. Mitscher LA. Organic Chemistry of Drugs Synthesis   Vol. 1-3:  Wiley-Interscience; New York: 1977. 
    Google Scholar
  • 6 DeArriba AF. Gómez-Casajús LA. Cavalcanti F. Almansa C. García-Rafanell J. Forn J. Eur. J. Pharmacol.  1996,  318:  341 
    CrossrefGoogle Scholar
  • 7 DeArriba AF. Gómez-Casajús LA. Cavalcanti F. Almansa C. García-Rafanell J. J. Med. Chem.  1997,  40:  547 
    CrossrefGoogle Scholar
  • 8 Harper RW. Jackson WT. Froelich LL. Boyd RJ. Aldridge TE. Herron DK. J. Med. Chem.  1994,  37:  2411 
    CrossrefGoogle Scholar
  • 9a Ishii S, Yagi K, Umehara T, Kudo M, Nawamaki T, and Watanabe S. inventors; Jpn. Kokai Tokkyo Koho JP  02129171. 
  • 10a Buntain IG, Hatton LR, Hawkins DW, Pearson CJ, and Roberts DA. inventors; Eur. Pat. Appl. EP  295117. 
  • 11a Shirakava K. Tsujikawa T. Takeda Kenkyusho Nempo  1963,  22:  19 
    Google Scholar
  • 12a Naito T, Oshima Y, Yoshikawa T, Kasahara A, Domori R, Nakai Y, and Tsukada W. inventors; S. African Pat.  6704936. 
  • 13 Joule JA. Smith GF. Heterocyclic Chemistry   Van Nostrand; London: 1972. 
    Google Scholar
  • 14 Badawey El-SAM. J. Heterocycl. Chem.  1996,  33:  229 
    CrossrefGoogle Scholar
  • 15 Zanatta N. Fagundes MB. Ellensohn R. Marques M. Bonacorso HG. Martins MAP. J. Heterocycl. Chem.  1998,  35:  451 
    CrossrefGoogle Scholar
  • 16 Bonacorso HG. Oliveira MR. Wentz AP. Wastowski AD. de Oliveira AB. Hörner M. Zanatta N. Martins MAP. Tetrahedron  1999,  55:  345 
    CrossrefGoogle Scholar
  • 17 Bonacorso HG. Wastowski AD. Zanatta N. Martins MAP. Naue JA. J. Fluorine Chem.  1998,  92:  23 
    CrossrefGoogle Scholar
  • 18 Martins MAP. Freitag R. Flores AFC. Zanatta N. Synthesis  1995,  1491 
    Article in Thieme ConnectGoogle Scholar
  • 19 Bonacorso HG. Bittencourt SRT. Wastowski AD. Wentz AP. Zanatta N. Martins MAP. Tetrahedron Lett.  1996,  37:  9155 
    CrossrefGoogle Scholar
  • 20 Bonacorso HG. Bittencourt ST. Lourega RV. Flores AFC. Zanatta N. Martins MAP. Synthesis  2000,  1431 
    Article in Thieme ConnectGoogle Scholar
  • 21 Colla A. Martins MAP. Clar G. Krimmer S. Fischer P. Synthesis  1991,  483 
    Article in Thieme ConnectGoogle Scholar
  • 22 Bonacorso HG. Bittencourt SRT. Martins MAP. Lourega R. Zanatta N. Flores AFC. J. Fluorine Chem.  1999,  99:  177 
    CrossrefGoogle Scholar
  • 23a Flores AFC. Siqueira GM. Freitag R. Zanatta N. Martins MAP. Química Nova  1994,  17:  298 
    Google Scholar
  • 24a Siqueira GM. Flores AFC. Clar G. Zanatta N. Martins MAP. Química Nova  1994,  17:  24 
    Google Scholar
  • 25 Cunha CC. Clereci E. Martins MAP. Zanatta N. J. Heterocycl. Chem.  1995,  32:  735 
    Google Scholar