Synthesis of 1-substituted 5-aryl-3-styryl-2-pyrazolines and 3-aryl-5-styryl-2-pyrazolines by the reaction of dibenzylideneacetones and E,E-cinnamylideneacetophenones with hydrazines

Journal of Heterocyclic Chemistry

Volumn 43, Issue 5, 2006, Pages 1303-1309

  Lévai, Albert ^a   Jeko, József ^b  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b Department of Agricultural Sciences and Environmental Management   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

(2 CARBOXYPHENYL)HYDRAZINE; (4 CARBOXYPHENYL)HYDRAZINE; 1 (2 CARBOXYPHENYL) 5 (4 CHLOROPHENYL) 3 (4 CHLOROSTYRYL) 2 PYRAZOLINE; 1 (2 CARBOXYPHENYL) 5 PHENYL 3 STYRYL 2 PYRAZOLINE; 1 (4 CARBOXYPHENYL) 3 (4 METHYLPHENYL) 5 STYRYL 2 PYRAZOLINE; 1 (4 CARBOXYPHENYL) 3 PHENYL 5 STYRYL 2 PYRAZOLINE; 1 (4 CARBOXYPHENYL) 5 (4 CHLOROPHENYL) 3 (4 CHLOROSTYRYL) 2 PYRAZOLINE; 1 (4 CARBOXYPHENYL) 5 (4 METHOXYPHENYL) 3 (4 METHOXYSTYRYL) 2 PYRAZOLINE; 1 (4 CARBOXYPHENYL) 5 (4 METHYLPHENYL) 3 (4 METHYLSTYRYL) 2 PYRAZOLINE; 1 (4 CARBOXYPHENYL) 5 PHENYL 3 STYRYL 2 PYRAZOLINE; 3 (2 HYDROXYPHENYL) 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 3 (4 CHLOROPHENYL) 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 3 (4 FLUOROPHENYL) 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 3 (4 METHOXYPHENYL) 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 3 (4 METHYLPHENYL) 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 3 (5 CHLORO 2 HYDROXYPHENYL) 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 3 PHENYL 1 PROPIONYL 5 STYRYL 2 PYRAZOLINE; 5 (2 CHLOROPHENYL) 3 (2 CHLOROSTYRYL) 1 PROPIONYL 2 PYRAZOLINE; 5 (2,4 DICHLOROPHENYL) 3 (2,4 DICHLOROSTYRYL) 1 PROPIONYL 2 PYRAZOLINE; 5 (4 CHLOROPHENYL) 3 (4 CHLOROSTYRYL) 1 PROPIONYL 2 PYRAZOLINE; 5 (4 METHOXYPHENYL) 3 (4 METHOXYSTYRYL) 1 PROPIONYL 2 PYRAZOLINE; 5 (4 METHYLPHENYL) 3 (4 METHYLSTYRYL) 1 PROPIONYL 2 PYRAZOLINE; 5 PHENYL 1 PROPIONYL 3 STYRYL 2 PYRAZOLINE; ACETIC ACID; ACETOPHENONE DERIVATIVE; CINNAMALDEHYDE; HYDRAZINE; HYDRAZINE DERIVATIVE; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 33750937715     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430524     Document Type: Article

References (45)

1. J. Elguero, in Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. Scriven, eds, Pergamon Press, Oxford, 3, 1 (1996) .
2. A. Lévai, Khim. Geterotsikl. Soedin., 747 (1997).
3. A. Lévai, J. Heterocyclic Chem., 39, 1 (2002).
4. R. E. Brown and J. Shavrel, Jr., US Patent 3,624,102 (1972); Chem. Abstr., 76, 59618 (1972).
5. K. Ramalingham, G. X. Thyvekikakath, K. D. Berlin, R. W. Chesnut, R. A. Brown, N. N. Durham, A. E. Ealick and D. van der Helm, J. Med. Chem., 20, 847 (1977).
6. D. Nauduri and G. B. S. Reddy, Chem. Pharm. Bull., 46, 1254 (1998).
7. J. G. Lombardino and I. G. Otternes, J. Med. Chem., 24, 830 (1981).
8. E. Fischer and O. Knövenagel, Ann. Chem., 239, 194 (1887).
9. L. C. Raiford and W. Peterson, J. Org. Chem., 1, 544 (1936).
10. L. C. Raiford and G. V. Gundy, J. Org. Chem., 3, 265 (1938).
11. W. Ried and G. Dankert, Chem. Ber., 90, 2707 (1957).
12. R. H. Wiley, C. H. Jarboe, F. N. Hayes, E. Hansbury, J. T. Nielsen, P. X. Callahan and M. C. Sellars, J. Org. Chem., 23, 732 (1958).
13. A. E. A. Sammour, Tetrahedron, 20, 1067 (1964).
14. I. Bhatnagar and M. V. George, Tetrahedron, 24, 1293 (1968).
15. J. L. Aubagnac, J. Elguero and R. Jacquier, Bull. Soc. Chim. Fr., 3292 (1969).
16. F. G. Weber, K. Brosche, C. Seedorf and A. Rinow, Monatsh. Chem., 100, 1924 (1969).
17. M. G. Joshi and K. N. Wadodkar, Indian J. Chem., 20B, 1090 (1981).
18. T. C. Sharma, S. R. Pawar and R. J. Reddy, Acta Chim. Hung., 112, 159 (1983).
19. A. Lévai, Á. Szöllosy and G. Tóth, J. Chem. Research (S), 392 (1985).
20. G. Tóth, Á. Szöllosy, T. Lóránd, T. Kónya, D. Szabó, A. Földesi and A. Lévai, J. Chem. Soc. Perkin Trans. 2, 319 (1989).
21. Á. Szöllosy, G. Tóth, T. Lóránd, T. Kónya, F. Aradi and A. Lévai, J. Chem. Soc. Perkin Trans. 2, 489 (1991).
22. A. A. Bilgin, E. Palaska, R. Sunal and B. Gümüsel, Pharmazie, 49, 67 (1994).
23. N. Mishriky, F. M. Asaad, Y. A. Ibrahim and A. S. Girgis, Pharmazie, 51, 544 (1996).
24. A. Lévai, J. Heterocyclic Chem., 35, 13 (1998).
25. A. Lévai, Heterocycl. Commun., 5, 151 (1999).
26. S. R. Dighade and M. M. Chincholkar, Asian J. Chem., 13, 1606 (2001).
27. P. Wang, N. Onozawa-Komatsuzaki, Y. Himeda, H. Sugihara, H. Arakawa and K. Kasuga, Tetrahedron Lett., 42, 9199 (2001).
28. F. Manna, F. Chimenti, A. Balosco, D. Secci, B. Bizzarri, O. Befani, P. Turini, B. Mondovi, S. Alcaro and A. Tafi, Bioorg. Med. Chem. Lett., 12, 3629 (2002).
29. A. Lévai, T. Patonay, A. M. S. Silva, D. C. G. A. Pinto and J. A. S. Cavaleiro, J. Heterocyclic Chem., 39, 751 (2002).
30. A. Lévai, Heterocycl. Commun., 9, 287 (2003).
31. A. Lévai, A. M. S. Silva, D. C. G. A. Pinto, J. A. S. Cavaleiro, I. Alkorta, J. Elguero and J. Jeko, Eur. J. Org. Chem., 4672 (2004).
32. A. Lévai, Arkivoc, 344 (2005(IX)).
33. A. Lévai and J. Jeko, Arkivoc, 199 (2005(X)).
34. A. Lévai, J. Jeko and D. I. Brahmbhatt, J. Heterocyclic Chem., 42, 1231 (2005).
35. A. Lévai and J. Jeko, J. Heterocyclic Chem., 43, 111 (2006)
36. A. Lévai and J. Jeko, Monatsh. Chem., 137, 339 (2006).
37. F. Straus, Ber. Dtsch. Chem. Ges., 51, 1457 (1918).
38. L. C. Raiford and R. H. Manley, J. Org. Chem., 5, 590 (1940).
39. H. Ferres, M. S. Hamdam and W. R. Jackson, J. Chem. Soc. B, 1892 (1971).
40. J. Grimshaw and J. Trocha-Grimshaw, J. Chem. Soc. Perkin Trans. 1, 1383 (1974).
41. D. B. Reddy, A. Padmaja and V. Padmavathi, Indian J. Chem., 348, 811 (1995).
42. D. C. G. A. Pinto, A. M. S. Silva, J. A. S. Cavaleiro, C. Foces-Foces, A. L. Llamas-Saiz, N. Jagerovic and J. Elguero, Tetrahedron, 55, 10187 (1999).
43. D. C. G. A. Pinto, A. M. S. Silva, A. Lévai, J. A. S. Cavaleiro, T. Patonay and J. Elguero, Eur. J. Org. Chem., 2593 (2000).
44. E. E. Baroni, K. A. Kobyrzina and E. A. Anreesheb, Zh. Oshch. Khim., 30, 2002 (1960).
45. W. Fliege, R. Huisgen, W. Kolbeck and V. Veberndörfer, Chem. Ber., 116, 3438 (1983).