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

E. I.  Klimova; G. M.  Martinez; B. T.  Klimova; Z. C.  Damian; S.  Ortega; I. D.  Mendez; P. R.  Gutiérrez; G. R. A.  Vazquez

doi:10.1055/s-2002-33917

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2002(13): 1891-1897
DOI: 10.1055/s-2002-33917

PAPER

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

E. I. Klimova^a, G. M. Martinez*^a, B. T. Klimova^a, Z. C. Damian^a, S. Ortega^a, I. D. Mendez^a, P. R. Gutiérrez^b, G. R. A. Vazquez^b
^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

Further Information

Publication History

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

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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

Search in Google Scholar
2 Auwers K. Heimke P. Liebigs Ann. Chem. 1927, 458: 186

Search in Google Scholar
3 Raiford LC. Tanzer LK. J. Org. Chem. 1941, 6: 722

Search in Google Scholar
4 Sayed GH. Indian J. Chem. 1980, 19b: 364

Search in Google Scholar
5 Oszbach Gy. Szabo D. Acta Chim. Acad. Sci. Hung. 1975, 86: 449 ; Chem. Abstr. 1976, 84, 30958

Search in 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

Crossref Search in Google Scholar
9 Klimova E. Ruiz L. Martinez GM. Espinosa P. Meleshonkova N. Russ. Chem. Bull. 1996, 45: 2740

Search in Google Scholar
10 Klimova E. Martinez M. Klimova T. Alvarez T. Toscano A. Ruiz L. J. Organomet. Chem. 1999, 585: 106

Crossref Search in Google Scholar
11 Klimova E. Martinez M. Klimova T. Ruiz L. Russ. Chem. Bull. 2000, 49: 906

Crossref Search in Google Scholar
12 Tose N. Nakaya H. Takeda Y. Brit. J. Pharmacol. 1995, 114: 1076

Search in Google Scholar
13 Regan J. Bruno J. Mc Garry D. Bioorg. Med. Chem. Lett. 1998, 8: 2737

Crossref Search in Google Scholar
14 Mock C. Puscasu I. Rauterkus MJ. Inorg. Chim. Acta 2000, 319: 109

Search in Google Scholar
15 Chimirri A. Monforte P. Musumeci L. Arch. Pharm. (Weinheim, Ger.) 2001, 334: 203

Search in 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

Crossref PubMed Search in Google Scholar
17 Malinka W. Pharmazie 2001, 56: 384

Search in Google Scholar
18 Chang CH. Porter RF. Bauer SH. J. Am. Chem. Soc. 1970, 92: 5313

Crossref Search in Google Scholar
19 Tables of Interatomic Distances and Configuration in Molecules and Ions Suttonm LE. Chemical Society; London: 1965.
20 Gau AH. Lein GL. Uang BJ. Liao FL. J. Org. Chem. 1999, 64: 2194

Crossref Search in Google Scholar
21 Vassilikogiannakis G. Stratakis M. Karabatsos GJ. Orfanopoulos M. J. Heterocycl. Chem. 1996, 33: 993

Search in Google Scholar