Synthesis of 3-benzoyl-4-styryl-2-pyrazolines and their oxidation to the corresponding pyrazoles

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2593-2599

  Pinto, Diana C G A ^a   Silva, Artur M S ^a   Lévai, Albert ^b   Cavaleiro, José A S ^a   Patonay, Tamás ^b   Elguero, José ^c  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

(E,E) Cinnamylideneacetophenones; Cycloadditions; Nitrogen heterocycles; NMR spectroscopy

Indexed keywords

DIAZOMETHANE; PYRAZOLE DERIVATIVE; PYRAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033858779     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2593::aid-ejoc2593>3.3.co;2-p     Document Type: Article

References (30)

1. Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings (Ed.: R. H. Wiley), in The Chemistry of Heterocyclic Compounds (Ed: A. Weissberger), Interscience Publishers, New York, 1967, Vol. 22, p. 180-278.
2. J. Elguero, in Comprehensive Heterocyclic Chemistry (Ed: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, Vol. 5, p. 167-302; J. Elguero, in Comprehensive Heterocyclic Chemistry II (Ed: A. R. Katritzky, C. W. Rees, E. F. Scriven), Pergamon, Oxford, 1996, Vol. 3, p. 1-75.
3. J. Elguero, in Comprehensive Heterocyclic Chemistry (Ed: A. R. Katritzky, C. W. Rees), Pergamon, Oxford, 1984, Vol. 5, p. 167-302; J. Elguero, in Comprehensive Heterocyclic Chemistry II (Ed: A. R. Katritzky, C. W. Rees, E. F. Scriven), Pergamon, Oxford, 1996, Vol. 3, p. 1-75.
4. J. Elguero, A. Fruchier, J. Chem. Res. (R) 1990, 200-201; J. Chem. Res. (M) 1990, 1501-1509.
5. J. Elguero, A. Fruchier, J. Chem. Res. (R) 1990, 200-201; J. Chem. Res. (M) 1990, 1501-1509.
6. M. Begtrup, G. Boyer, P. Cabildo, C. Cativiela, R. M. Claramunt, J. Elguero, J. I. Garcia, C. Toiron, P. VedsØ, Magn. Reson. Chem. 1993, 31, 107-168.
7. A. Lévai, Khim. Geterotsikl. Soedin. 1997, 747-759.
8. I. Bhatnagar, M. V. George, Tetrahedron 1968, 24, 1293-1298. W. Ried, R. Lantzsch, Chem. Ber. 1969, 102, 378-379; R. N. Butler, Chem. Rev. 1984, 84, 249-276.
9. I. Bhatnagar, M. V. George, Tetrahedron 1968, 24, 1293-1298. W. Ried, R. Lantzsch, Chem. Ber. 1969, 102, 378-379; R. N. Butler, Chem. Rev. 1984, 84, 249-276.
10. I. Bhatnagar, M. V. George, Tetrahedron 1968, 24, 1293-1298. W. Ried, R. Lantzsch, Chem. Ber. 1969, 102, 378-379; R. N. Butler, Chem. Rev. 1984, 84, 249-276.
11. J. Azzarello, Gazz. Chim. Ital. 1906, 36, 50-55.
12. A. L. Tõkés, Á. Szöllõsy, G. Tóth, A. Lévai, Acta Chim. Hung. 1983, 112, 335-341.
13. A. Lévai, Monatsh. Chem., 1995, 126, 1245-1251; A. Lévai, Z. Cziáky, J. Jekõ, Z. Szabó, Indian J. Chem. 1996, 35B, 1091-1096; M. Regitz, H. Heydt, in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), John Wiley & Sons, New York, 1994, vol. 1, p. 393-558.
14. A. Lévai, Monatsh. Chem., 1995, 126, 1245-1251; A. Lévai, Z. Cziáky, J. Jekõ, Z. Szabó, Indian J. Chem. 1996, 35B, 1091-1096; M. Regitz, H. Heydt, in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), John Wiley & Sons, New York, 1994, vol. 1, p. 393-558.
15. A. Lévai, Monatsh. Chem., 1995, 126, 1245-1251; A. Lévai, Z. Cziáky, J. Jekõ, Z. Szabó, Indian J. Chem. 1996, 35B, 1091-1096; M. Regitz, H. Heydt, in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), John Wiley & Sons, New York, 1994, vol. 1, p. 393-558.
16. D. C. G. A. Pinto, A. M. S. Silva, L. M. P. M. Almeida, J. A. S. Cavaleiro, A. Lévai, T. Patonay, J. Heterocycl. Chem. 1998, 35, 217-224.
17. M. C. Caturla, J. Salomó, M. Soler, L. Martínez, R. Roser, J. Pharmaceut. Biomed. 1991, 9, 1181-1184; J. A. Hueso-Rodriguez, J. Berrocal, B. Gutiérrez, A. J. Farré, J. Frigola, Bioorg. Med. Chem. Lett. 1993, 3, 269-272.
18. M. C. Caturla, J. Salomó, M. Soler, L. Martínez, R. Roser, J. Pharmaceut. Biomed. 1991, 9, 1181-1184; J. A. Hueso-Rodriguez, J. Berrocal, B. Gutiérrez, A. J. Farré, J. Frigola, Bioorg. Med. Chem. Lett. 1993, 3, 269-272.
19. J. A. Alexandrova, N. A. Dorofeeva, A. V. Chernova, U. K. Kairullin, Zh. Org. Khim. 1978, 14, 1974-1978.
20. T. Sammakia, in Encyclopedia of Reagents for Organic Synthesis (Ed: L. A. Paquette), John Wiley & Sons, Chichester, 1995, Vol. 2. p. 1512-1519.
21. A. M. S. Silva, J. A. S. Cavaleiro, J. Elguero, Liehigs Ann./Recueil 1997, 2065-2068.
22. A. M. S. Silva, D. C. G. A. Pinto, H. R. Tavares, J. A. S. Cavaleiro, M. L. Jimeno, J. Elguero, Eur. J. Org. Chem. 1998, 2031-2038.
23. cis is relative to H-4.
24. J. Elguero, C. Marzin, P. Linda, A. R. Katritzky, The Tautomerism of Heterocycles, Academic Press, New York, 1976; V. I. Minkin, A. D. Garnovskii, J. Elguero, A. R. Katritzky, O. V. Denisco, The Tautomerism of Heterocycles, Chapter 4. "Five-Membered Rings with Two or More Heteroatoms", Adv. Heterocycl. Chem. 2000, 76, in press.
25. J. Elguero, C. Marzin, P. Linda, A. R. Katritzky, The Tautomerism of Heterocycles, Academic Press, New York, 1976; V. I. Minkin, A. D. Garnovskii, J. Elguero, A. R. Katritzky, O. V. Denisco, The Tautomerism of Heterocycles, Chapter 4. "Five-Membered Rings with Two or More Heteroatoms", Adv. Heterocycl. Chem. 2000, 76, in press.
26. L. Infantes, C. Foces-Foces, R. M. Claramunt, C. López, N. Jagerovic, J. Elguero, Heterocycles 1999, 50, 227-242.
27. L. G. Tensmeyer, C. Ainsworth, J. Org. Chem. 1966, 31, 1878-1883.
28. 13C NMR Spectroscopy, 2nd Edition, Verlag Chemie, Weinheim, 1978.
29. K. Lee, D. Y. Oh, Synthesis 1991, 213-214.
30. Diazomethane was bubbled through the flask containing the solution of each (E,E)-cinnamylideneacetophenone 1a-d; the saturation of the solution was complete when another flask, connected to the first one, containing diethyl ether became yellow. Caution: Diazomethane is a highly toxic, explosive gas. See: The Merck Index, Eleventh Edition, Published by Merck and Co., Inc., Rahway, NJ, USA, Compound N° 2983, 1989, p. 473.