A new, efficient and chemoselective one-pot protocol for synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones from aryl aldehyde bisulfite adducts promoted by POCl3

Journal of Heterocyclic Chemistry

Volumn 45, Issue 3, 2008, Pages 683-686

  Khosropour, Ahmad R ^a   Khodaei, Mohammad M ^b   Hoseini Jomor, Seyed J ^b  

^a UNIVERSITY OF ISFAHAN   (Iran)

^b RAZI UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

4 ARYLIDENE 2 PHENYL 5 OXAZOLONE DERIVATIVE; ARYL ALDEHYDE BISULFITE; BISULFITE; CHLORIDE; OXAZOLE DERIVATIVE; PHOSPHORUS CHLORIDE OXIDE; PHOSPHORUS OXYCHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION;

EID: 44349108839     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450308     Document Type: Article

References (42)

1. (a) Mitra, S. N.; Dey, S.; Karthikeyan, S.; Singh, T. P. Biopolymers, 1997, 41, 1997;
2. (b) Cavalier, F.; Verducci, J. Tetrahedron Lett., 1995, 36, 4425.
3. (a) Bautista, F. M.; Campelo, J. M.; Garcia, D. L. ; Marinas, J. M. Amino Acids 1992, 2, 87.
4. (b) Cativela, C.; Diaz-de-Villegas, M. D.; Garcia, J. I.; Jimenez, A. I. Tetrahedron 1997, 53, 4479.
5. (c) Meiwes, J.; Schudock, M.; Kretzschmar, G. Tetrahedron Asymmetry 1997, 8, 527.
6. (d) Gootwald, K.; Seebach, D. Tetrahedron 1999, 55, 723.
7. (e) Konkel, J. T.; Fan, J.; Jayachandran, B.; Kirk, K. L. J. Fluorine Chem. 2002, 115, 27.
8. Abd-el-Rahm, A. H.; Kandeel, E. M.; Abdel-Razik, E. A.; El-Ghamry, I. A. An. Quim. 1993, 89, 237.
9. Gelmi, M. L.; Clerici, F.; Meus, A. Tetrahedron 1997, 53, 1843.
10. (a) Penalba, J.; Puchades, R.; Maquieira, A.; Gee, S.; Hammock, B. D. Biosens. Bioelectron. 2000, 15, 99.
11. (b) Chikere, A. C.; Galunsky, B.; Schünemann, V.; Kasche, V. Enzyme. Microb. Technol. 2001, 28, 168.
12. (a) Bossio, R.; Marcaccini, S.; Pepino, R.; Paoli, P. J. Heterocycl. Chem. 1994, 31, 729.
13. (b) Cannella, R.; Clerici, F.; Gelmi, M. L.; Penso, M.; Pocar, D. J. Org. Chem. 1996, 61, 1854.
14. (c) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M. Tetrahedron Lett. 2002, 43, 4167.
15. (a) R. Filler, Advances in Heterocyclic Chemistry, A. R. Katritzky, A. J. Boulton, and J. M. Lagowski (eds.), Vol. 4, Academic Press, New York (1965), p. 75.
16. (b) R. Filler and Y. S. Rao, Advances in Heterocyclic Chemistry, A. R. Katritzky and A. J. Boulton (eds.), Vol. 21, Academic Press, New York (1977), p. 198.
17. (c) Y. S. Rao and R. Filler, Oxazoles, edited by I. J. Turchi, John Wiley and Sons, New York (1986), p. 361.
18. Baltazzi, E.; Davis, E. A. Chem. Ind. (London) 1962, 929.
19. (a) Cativiela, C.; Melendez, E. Synthesis 1978, 832.
20. (b) Cativiela, C.; Diaz-de-Villegas, M. D.; Galvez, J. A. Tetrahedron Lett. 1999, 40, 1027.
21. Rao, Y. S. J. Org. Chem. 1976, 41, 722.
22. Kashyap, J.; Chetry, A. B.; Das, P. J. Synth. Commun. 1998, 28, 4187.
23. Bautista, F. M.; Campelo, J. M.; Garcia, A.; Luna, D.; Marinas, J. M.; Romero, A. A. J. Chem. Soc. Perkin Trans 2, 2002, 227.
24. (a) Rao, P. S.; Venkatratnam, R. V. Indian J. Chem. 1994, 33B, 984.
25. (b) Kidwai, M.; Kumar, R.; Kumar, P. Indian J. Chem. 1996, 35B, 1004.
26. Monk, K. A.; Sarapa, D.; Mohan, R. S. Synth. Commun. 2000, 30, 3167.
27. Paul, S.; Nanda, P.; Gupta, R.; Loupy, A. Tetrahedron Lett. 2004, 45, 425.
28. Khodaei, M. M.; Khosropour, A. R.; Hoseini Jomor, S. J. J. Chem. Res.(S) 2003, 638.
29. Wei, X.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 3815.
30. (a) Vogel, A. I. Textbook of Practical Organic Chemistry, London, ELBS and Longman, 1978, p. 761.
31. (b) Khusid, A. Kh.; Chizhova, N. V. J. Org. Chem. USSR (Engl. Transl.) 1985, 21, 37.
32. (c) Mitra, A. K; De, A.; Karchaudhuri, N. J. Chem. Res.(S) 1999, 560.
33. (d) Kjell, D. P.; Slattery, B. J.; Semo, M. J. Org. Chem. 1999, 64, 5722.
34. (a) Huma, H. Z. S.; Halder, R.; Kalra, S. S.; Das, J.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6485.
35. (b) Bagley, M. C.; Cale, J. W.; Bower, J. Chem. Commun. 2002, 1682.
36. (c) Dallinger, D.; Gorobets, N. Y.; Kappe, C. O. Org. Lett. 2003, 5, 1205.
37. (d) Bora, U.; Saikia, A.; Boruah, R. C. Org. Lett. 2003, 5, 435.
38. (a) Khodaei, M. M.; Khosropour, A. R.; Beygzadeh, M. Synth. Commun. 2004, 34, 1551.
39. (b) Mohammadpoor-Baltork, I.; Khosropour, A. R.; Hojati, S. F. Catal. Commun. 2007, 8, 200.
40. (c) Khosropour, A. R.; Mohammadpoor-Baltork, I.; Khodaei, M. M.; Ghanbary, P. Z. Naturforsch. B, 2007, 62b, 537.
41. (d) Mohammadpoor-Baltork, I.; Khosropour, A. R.; Hojati, S. F. Monatshefte für Chemie 2007, 138, 663.
42. (e) Khosropour, A. R.; Khodaei, M. M.; Beygzadeh, M.; Heteroatom Chem. 2007, 18, 684.