Clean and atom-economic synthesis of α-phenylselenoacrylonitriles and α-phenylseleno-α,β-unsaturated esters by Knoevenagel reaction under solvent-free conditions

Journal of the Brazilian Chemical Society

Volumn 16, Issue 4, 2005, Pages 857-862

  Perin, Gelson ^a   Jacob, Raquel G ^b   Botteselle, Giancarlo V ^a   Kublik, Emerson L ^a   Lenardão, Eder J ^a   Cella, Rodrigo ^b,c   Silva Dos Santos, Paulo César ^b  

^a FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Knoevenagel condensation; Phenylselenoacrylonitriles; Solvent free reaction

Indexed keywords

EID: 24044544582     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532005000500027     Document Type: Article

References (37)

1. Wessjohann, L. A.; Sinks, U.; J. Prakt. Chem. 1998, 340, 189;
2. Wirth, T.; Tetrahedron 1999, 55, 1;
3. Ponthieux, S.; Paulmier, C. In Topics in Current Chemistry. Organoselenium Chemistry: Modern Developments in Organic Synthesis; Wirth, T. ed., Springer: Berlin, 2000, p. 113-142.
4. Comasseto, J. V.; Ling, L. W.; Petragnani, N.; Stefani, H. A.; Synthesis 1997, 373.
5. De Cock, Ch.; Piettre, S.; Lahousse, F.; Janousek, Z.; Merényi, R.; Viehe, H. G.; Tetrahedron 1985, 41, 4183.
6. Silveira, C. C.; Perin, G.; Braga, A. L.; Dabdoub, M. J.; Jacob, R. G.; Tetrahedron 2001, 57, 5953.
7. Martin, C.; Mailliet, P.; Madaluno, J.; Org. Lett. 2000, 2, 923;
8. Silveira, C. C.; Nunes, M. R. S.; Wendling, E.; Braga, A. L.; J. Organomet. Chem. 2001, 623, 131.
9. Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.; Parlanti, L.; Piancatelli, G.; Tetrahedron Lett. 2000, 41, 561;
10. D'Onofrio, F.; Margarita, R.; Parlanti, L.; Piancatelli, G.; Sbraga, M.; J. Chem. Soc., Chem. Commun. 1998, 185;
11. D'Onofrio, F.; Parlanti, L.; Piancatelli, G.; Synlett 1996, 63;
12. Angoh, A. G.; Clive, D. L. J.; J. Chem. Soc., Chem. Commun. 1985, 941.
13. Lebarillier, L.; Outurquin, F.; Paulmier, C.; Tetrahedron 2000, 56, 7483.
14. Lebarillier, L.; Outurquin, F.; Paulmier, C.; Tetrahedron 2000, 56, 7495.
15. Silveira, C. C.; Botega, C. S.; Rhoden, C. R. B.; Nunes, M. R. S.; Braga, A. L.; Lenardão, E. J.; Synth. Commun. 1998, 28, 3371;
16. For a review on the use of Wittig and Wittig-Horner reactions in preparation of vinyl chalcogenides, see: Silveira, C. C.; Perin, G.; Jacob, R. G.; Braga, A. L.; Phosphorus, Sulfur Silicon Relat. Elem. 2001, 172, 55.
17. Janousek, Z.; Piettre, S.; Gorissen-Hervens, F.; Viehe, H. G.; J. Organomet. Chem. 1983, 250, 197;
18. Piettre, S.; Janousek, Z.; Merényi, R.; Viehe, H. G.; Tetrahedron 1985, 41, 2527.
19. Deng, G-S.; Huang, Z-Z.; Huang, X.; Synth. Commun. 2002, 32, 1775.
20. Tietze, L.; Beifuss, U. In Comprehensive Organic Synthesis; Heathcock, C., ed., Pergamon Press: Oxford, 1991; vol. 2, p. 341-394.
21. Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J.; Tetrahedron 2003, 59, 3753;
22. Sebti, S.; Tahir, R.; Nazih, R.; Saber, A.; Boulaajaj, S.; Appl. Cat. A: General 2002, 225, 155;
23. For a review on the use of clay-supported reagents in organic synthesis, see: Varma, R. S.; Tetrahedron 2002, 58, 1235.
24. Rand, L.; Swisher, J. V.; Cronix, C. J.; J. Org. Chem. 1962, 27, 3505;
25. Rand, L.; Haiduchewych, D.; Dolinski, R. J.; J. Org. Chem. 1966, 31, 1272;
26. For a review on fluoride ion as a base in organic synthesis, see: Clark, J. H.; Chem. Rev. 1980, 80, 429.
27. Texier-boullet, F.; Villemin, D.; Ricard, M.; Moison, H.; Foucaud A.; Tetrahedron 1985, 41, 1259;
28. Nakano, Y.; Shi, W.; Nishii, Y.; Igarashi, M.; J. Heterocyclic Chem. 1999, 36, 33;
29. 3 mediated organic synthesis, see: Blass, B. E.; Tetrahedron 2002, 58, 9301.
30. Jacob, R. G.; Perin, G.; Loi, L. N.; Pinno, C. S.; Lenardão, E. J.; Tetrahedron Lett. 2003, 44, 3605.
31. Jacob, R. G.; Perin, G.; Botteselle, G. V.; Lenardão, E. J.; Tetrahedron Lett. 2003, 44, 6809.
32. Basu, B.; Jha, S.; Mridha, N. K.; Bhuiyan, M. H.; Tetrahedron Lett. 2002, 43, 7967.
33. α-Phenylselenoacetonitrile 1a was prepared according to: Martin-Esker, A. A.; Ko, S.; Newcomb, M.; J. Org. Chem. 1993, 58, 4691.
34. Ethyl phenylselenoacetate 1b was prepared according to: Reich, H. J.; Renga, J. M.; Reich, I. L.; J. Am. Chem. Soc. 1975, 97, 5434.
35. Robinson, C. N.; Shaffer, A. A.; Slater, C. D.; Gelbaum, L. T.; J. Org. Chem. 1993, 58, 3563.
36. For reviews on MW solvent-free using supported reagents, see: Varma, R. S.; Green Chem. 1999, 43;
37. Varma, R. S.; Pure Appl. Chem. 2001, 73, 193.