PDF herunterladen
Synthesis 2002(13): 1891-1897
DOI: 10.1055/s-2002-33917
PAPER
© Georg Thieme Verlag Stuttgart · New York

Ene Reactions of Arylmethylenedihydropyrazoles with 4-Phenyl-3H-1,2,4-triazole-3,5(4H)-dione

E. I. Klimovaa, G. M. Martinez*a, B. T. Klimovaa, Z. C. Damiana, S. Ortegaa, I. D. Mendeza, P. R. Gutiérrezb, G. R. A. Vazquezb
a Universidad Nacional Autónoma de México, Instituto de Química and Facultad de Química (UNAM), Circuito exterior, Coyoacán, México D.F., C.P. 04510, México
e-Mail: margarma@chem.ucla.edu; e-Mail: margar@servidor.unam.mx;
b Centro de Investigación, Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, Apdo, Postal 1067, C. P. 72001, Puebla, Pue, México
Weitere Informationen

Publikationsverlauf

Received 14 May 2002
Publikationsdatum:
09. September 2002 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

2-Acetyl-3-aryl-7-arylmethylene-3,4,5,6,7,9-hexahydro-
2H-indazoles enter into the ene reaction with 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione to give the corresponding monoene adducts. Under analogous conditions, 3-aryl-7-arymethylene-2-methyl-3,4,5,6,7,9-hexahydro-2H-indazoles give mono- and polyaddition products. The structures of compounds obtained were established using UV, IR, 1H and 13C NMR spectroscopy and X-ray diffraction analysis.

Key words

chalcones - Diels-Alder reactions - ene reactions - dihydropyrazoles

    References

  • 1 Freudenberg K. Stoll W. Liebigs Ann. Chem.  1924,  440:  38 
    Google Scholar
  • 2 Auwers K. Heimke P. Liebigs Ann. Chem.  1927,  458:  186 
    Google Scholar
  • 3 Raiford LC. Tanzer LK. J. Org. Chem.  1941,  6:  722 
    Google Scholar
  • 4 Sayed GH. Indian J. Chem.  1980,  19b:  364 
    Google Scholar
  • 5 Oszbach Gy. Szabo D. Acta Chim. Acad. Sci. Hung.  1975,  86:  449 ; Chem. Abstr. 1976, 84, 30958
    Google Scholar
  • 6 Krapcho CJ, and Turk CF. inventors; US Patent  3 957 762.  ; Chem. Abstr. 1976, 85, 63066
  • 7 Krapcho CJ, and Turk CF. inventors; US Patent  4 004 007.  ; Chem. Abstr. 1977, 86, 171443
  • 8 Krapcho CJ. Turk CF. J. Med. Chem.  1979,  22:  270 
    CrossrefGoogle Scholar
  • 9 Klimova E. Ruiz L. Martinez GM. Espinosa P. Meleshonkova N. Russ. Chem. Bull.  1996,  45:  2740 
    Google Scholar
  • 10 Klimova E. Martinez M. Klimova T. Alvarez T. Toscano A. Ruiz L. J. Organomet. Chem.  1999,  585:  106 
    CrossrefGoogle Scholar
  • 11 Klimova E. Martinez M. Klimova T. Ruiz L. Russ. Chem. Bull.  2000,  49:  906 
    CrossrefGoogle Scholar
  • 12 Tose N. Nakaya H. Takeda Y. Brit. J. Pharmacol.  1995,  114:  1076 
    Google Scholar
  • 13 Regan J. Bruno J. Mc Garry D. Bioorg. Med. Chem. Lett.  1998,  8:  2737 
    CrossrefGoogle Scholar
  • 14 Mock C. Puscasu I. Rauterkus MJ. Inorg. Chim. Acta  2000,  319:  109 
    Google Scholar
  • 15 Chimirri A. Monforte P. Musumeci L. Arch. Pharm. (Weinheim, Ger.)  2001,  334:  203 
    Google Scholar
  • 16 Zimmermann D. Janin YL. Brehm L. Brauner-Osborne H. Ebert B. Johansen TN. Madsen U. Krogsgaard-Larsen P. Eur. J. Med. Chem.  1999,  34:  967 
    CrossrefPubMedGoogle Scholar
  • 17 Malinka W. Pharmazie  2001,  56:  384 
    Google Scholar
  • 18 Chang CH. Porter RF. Bauer SH. J. Am. Chem. Soc.  1970,  92:  5313 
    CrossrefGoogle Scholar
  • 19 Tables of Interatomic Distances and Configuration in Molecules and Ions   Suttonm LE. Chemical Society; London: 1965. 
    Google Scholar
  • 20 Gau AH. Lein GL. Uang BJ. Liao FL. J. Org. Chem.  1999,  64:  2194 
    CrossrefGoogle Scholar
  • 21 Vassilikogiannakis G. Stratakis M. Karabatsos GJ. Orfanopoulos M. J. Heterocycl. Chem.  1996,  33:  993 
    Google Scholar