3(5)-(2-Hydroxyphenyl)-5(3)-styrylpyrazoles: Synthesis and diels - Alder transformations

European Journal of Organic Chemistry

Volumn , Issue 21, 2004, Pages 4348-4356

  Silva, Vera L M ^a   Silva, Artur M S ^a   Pinto, Diana C G A ^a   Cavaleiro, José A S ^a   Elguero, José ^b  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

DDQ; Dehydrogenation reactions; Diels Alder reactions; NMR spectroscopy; ortho Benzoquinodimethane; Pyrazoles

Indexed keywords

3 (2 HYDROXYPHENYL) 1 PHENYL 5 STYRYLPYRAZOLE; 3 (2 HYDROXYPHENYL) 5 (4 METHOXYSTYRYL) 1 PHENYLPYRAZOLE; 3 (2 HYDROXYPHENYL) 5 (4 METHOXYSTYRYL)PYRAZOLE; 3 (2 HYDROXYPHENYL) 5 (4 NITROSTYRYL) 1 PHENYLPYRAZOLE; 3 (2 HYDROXYPHENYL) 5 (4 NITROSTYRYL)PYRAZOLE; 3 (2 HYDROXYPHENYL) 5 [2 (3 PHENYL 1,2,3,4 TETRAHYDRONAPHTHYL)]PYRAZOLE; 3 (2 HYDROXYPHENYL) 5 [2 [3 (4 METHOXYPHENYL)] 1,2,3,4 TETRAHYDRONAPHTHYL]PYRAZOLE; 3 (2 HYDROXYPHENYL) 5 [2 [3 (4 METHOXYPHENYL)]NAPHTHYL]PYRAZOLE; 3 (2 HYDROXYPHENYL) 5 [2 [3 (4 NITROPHENYL)] 1,2,3,4 TETRAHYDRONAPHTHYL]PYRAZOLE; 3 (2 HYDROXYPHENYL) 5 STYRYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 1 PHENYL 3 [2 (3 PHENYL 1,2,3,4 TETRAHYDRONAPHTHYL)]PYRAZOLE; 5 (2 HYDROXYPHENYL) 1 PHENYL 3 [2 (3 PHENYLNAPHTHYL)]PYRAZOLE; 5 (2 HYDROXYPHENYL) 1 PHENYL 3 STYRYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 3 (4 METHOXYSTYRYL) 1 PHENYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 3 (4 NITROSTYRYL) 1 PHENYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 3 [2 [3 (4 METHOXYPHENYL) 1,2,3,4 TETRAHYDRONAPHTHYL]] 1 PHENYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 3 [2 [3 (4 METHOXYPHENYL]NAPHTHYL] 1 PHENYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 3 [2 [3 (4 NITROPHENYL) 1,2,3,4 TETRAHYDRONAPHTHYL]] 1 PHENYLPYRAZOLE; 5 (2 HYDROXYPHENYL) 3 [2 [3 (4 NITROPHENYL)]NAPHTHYL] 1 PHENYLPYRAZOLE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION;

EID: 8144231437     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400407     Document Type: Article

References (24)

1. J. Elguero, in Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. Scriven), Pergamon, Oxford, 1996, vol. 3, pp. 1-75.
2. F. Palacios, A. M. O. Retana, J. Pagalday, Tetrahedron 1999, 55, 14451-14458.
3. R. Oliveira, R. Sanmartin, E. Domínguez, J. Org. Chem. 2000, 65, 7010-7019.
4. J. Elguero, P. Goya, N. Jagerovic, A. M. S. Silva, Pyrazoles as Drugs: Facts and Fantasies, in Targets in Heterocyclic Systems - Chemistry and Properties (Eds.: O. A. Attanasi, D. Spinelli), Italian Society of Chemistry, 2002, vol. 6, pp. 52-98.
5. S. Recnik, J. Svete, B. Stanovnik, Heterocycles 2002, 57, 2091-2106.
6. [6a] J. Catalán, F. Fabero, M. S. Guijaro, R. M. Claramunt, M. D. Santa María, M. C. Foces-Foces, F. H. Cano, J. Elguero, R. Sastre, J. Am. Chem. Soc. 1990, 112, 747-759.
7. [6b] J. Catalán, F. Fabero, R. M. Claramunt, M. D. Santa Maria, M. C. Foces-Foces, F. H. Cano, M. Martínez-Ripoll, J. Elguero, R. Sastre, J. Am. Chem. Soc. 1992, 114, 5039-5048.
8. R. Ahmad, N. Ahmad, M. Zia-Ul-Haq, A. Wahid, J. Chem. Soc., Pak. 1996, 18, 38-41.
9. K. Takagi, M. Tanaka, Y. Murakami, H. Morita, T. Aotsuka, Eur. J. Med. Chem. Chim. Ther. 1986, 21, 65-69.
10. [9a] D. C. G. A. Pinto, A. M. S. Silva, J. A. S. Cavaleiro, C. Foces-Foces, A. Llamas-Sainz, N. Jagerovic, J. Elguero, Tetrahedron 1999, 55, 10187-10200.
11. [9b] D. C. G. A. Pinto, A. M. S. Silva, A. Lévai, J. A. S. Cavaleiro, T. Patonay, J. Elguero, Eur. J. Org. Chem. 2000, 2593-2599.
12. [9c] D. C. G. A. Pinto, A. M. S. Silva, J. A. S. Cavaleiro, J. Heterocycl. Chem. 2000, 37, 1629-1643.
13. [9d] A. M. S. Silva, D. C. G. A. Pinto, L. M. P. M. Almeida, J. A. S. Cavaleiro, J. Elguero, Eur. J. Org. Chem. 2002, 3807-3815.
14. [9e] D. C. G. A. Pinto, A. M. S. Silva, J. A. S. Cavaleiro, J. Elguero, Eur. J. Org. Chem. 2003, 747-755.
15. 4′-Methoxy-2-styrylchromone (4b) had spectroscopic and analytical data similar to those reported previously in: D. C. G. A. Pinto, A. M. S. Silva, J. A. S. Cavaleiro, A. Levai, T. Patonay, J. Heterocycl. Chem. 1998, 35, 217-224. (Chemical Equation Presented)
16. [11a] 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.
17. [11b] C. M. M. Santos, A. M. S. Silva, J. A. S. Cavaleiro, Eur. J. Org. Chem. 2003, 4575-4585.
18. S. P. Singh, D. Kumar, H. Batra, R. Naithani, I. Rozas, J. Elguero, Can. J. Chem. 2000, 78, 1109-1120.
19. [13a] A. M. S. Silva, A. M. G. Silva, A. C. Tomé, J. A. S. Cavaleiro, Eur. J. Org. Chem. 1999, 135-139.
20. [13b] D. C. G. A. Pinto, A. M. S. Silva, L. M. P. M. Almeida, J. R. Carrillo, A. Diaz-Ortiz, A. de la Hoz, J. A. S. Cavaleiro, Synlett 2003, 1415-1418.
21. M. P. Cava, A. A. Deana, J. Am. Chem. Soc. 1959, 81, 4266-4268.
22. [15a] A. Hosomi, H. Iguchi, J.-I. Sasaki, H. Sakurai, Tetrahedron Lett. 1982, 23, 551-554.
23. [15b] K. Fuji, S. P. Khanapure, M. Node, T. Kawabata, A. Ito, Tetrahedron Lett. 1982, 26, 779-782.
24. A. B. Turner, H. J. Ringold, J. Chem. Soc., (C) 1967, 1720-1730.