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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
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Publication History

Received 14 May 2002
Publication Date:
09 September 2002 (online)

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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

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