Microwave-assisted direct synthesis of 2-substituted benzoxazoles from carboxylic acids under catalyst and solvent-free conditions

Synlett

Volumn , Issue 9, 2005, Pages 1401-1404

  Kumar, Raj ^a   Selvam, C ^a   Kaur, Gurmeet ^a   Chakraborti, Asit K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

2 aminophenol; Benzoxazole; Carboxylic acid; Direct coupling; Metal free; Microwave

Indexed keywords

2 AMINOPHENOL; AROMATIC CARBOXYLIC ACID; BENZOXAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORINE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; METAL; SOLVENT;

ARTICLE; CATALYST; CROSS COUPLING REACTION; MICROWAVE IRRADIATION; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 20544472303     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-868509     Document Type: Article

References (40)

1. Sun, L.-Q.; Chen, J.; Bruce, M.; Deskus, J. A.; Epperson, J. R.; Takaki, K.; Johnson, G.; Iben, L.; Mahle, C. D.; Ryan, E.; Xu, C. Bioorg. Med. Chem. Lett. 2004, 14, 3799; and references therein.
2. Gong, B.; Hong, F.; Kohm, C.; Bonham, L.; Klein, P. Bioorg. Med. Chem. Lett. 2004, 14, 1455.
3. Paramshivappa, R.; Kumar, P. P.; Subba Rao, P. V.; Srinivasa Rao, A. Bioorg. Med. Chem. Lett. 2003, 13, 657.
4. Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Kerwin, S. M. Bioorg. Med. Chem. 2002, 10, 3997.
5. López-Tudanca, P. L.; Labeaga, L.; Innerárity, A.; Alonso-Cires, L.; Tapia, I.; Mosquera, R.; Orjales, A. Bioorg. Med. Chem. 2003, 11, 2709.
6. (a) Kočí, J.; Klimešová, V.; Waisser, K.; Kaustová, J.; Dahse, H.-M.; Möllmann, U. Bioorg. Med. Chem. Lett. 2002, 12, 3275.
7. (b) Temiz, Ö.; Ören, I.; Şener, E.; Yalçin, I.; Uçarturk, N. Il Farmaco 1998, 53, 337; and references cited therein.
8. Edwards, P. D.; Meyer, E. F.; Vijayalakshmi, J.; Tuthill, P. A.; Andisik, D. A.; Gomes, B.; Strimpler, A. J. Am. Chem. Soc. 1992, 114, 1854.
9. Lin, L. S.; Lanza, T. J. Jr.; Castonguay, L. A.; Kamenecka, T.; McCauley, E.; Riper, G. V.; Egger, L. A.; Mumford, R. A.; Tong, X.; MacCoss, M.; Schmidt, J. A.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2004, 14, 2331.
10. (a) Heynderickx, A.; Guglielmetti, R.; Dubest, R.; Aubard, J.; Samat, A. Synthesis 2003, 1112.
11. (b) Organic Photochromes; El'tsov, A. V., Ed.; Plenum Press: New York, 1990, 178.
12. (a) Heathcock, C. H. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Flemming, I., Eds.; Pergamon Press; New York, 1991.
13. (b) Reser, A.; Leyshon, L. J.; Saunders, D.; Mijovic, M. V.; Bright, A.; Bogie, J. J. Am. Chem. Soc. 1972, 94, 2414.
14. (a) Cohen, V. I.; Pourabass, S. J. Heterocycl. Chem. 1977, 14, 1321.
15. (b) Cohen, V. I. J. Heterocycl. Chem. 1979, 16, 13.
16. (a) Chen, C.; Chen, Y.-J. Tetrahedron Lett. 2004, 45, 113.
17. (b) Nadaf, R. N.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Mol. Catal. A: Chem. 2004, 214, 155.
18. (c) Pottorf, R. S.; Chadha, N. K.; Katevics, M.; Ozola, V.; Suna, E.; Ghane, H.; Regberg, T.; Player, M. R. Tetrahedron Lett. 2003, 44, 175.
19. Tauer, E.; Grellmann, K. H. J. Org. Chem. 1981, 46, 4252.
20. (a) Kawashita, Y.; Nakamichi, N.; Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5, 3713; and references therein.
21. (b) Wilfred, C. D.; Taylor, R. K. J. Synlett 2004, 1628.
22. (c) Bougrin, K.; Loupy, A.; Soufiaoudi, M. Tetrahedron 1998, 54, 8055.
23. Park, M. S.; Jun, K.; Shin, S. R.; Oh, S. W.; Park, K. H. J. Heterocycl. Chem. 2002, 39, 1279; and references therein.
24. (a) El-Sheikh, M. I.; Marks, A.; Biehl, E. R. J. Org. Chem. 1981, 46, 3256.
25. (b) Park, Y.-T.; Jung, C.-H.; Kim, K.-W. J. Org. Chem. 1999, 64, 8546.
26. Wang, F.; Hauske, J. R. Tetrahedron Lett. 1997, 37, 6529.
27. DeLuca, M. R.; Kerwin, S. M. Tetrahedron 1997, 53, 457.
28. Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 6646.
29. Kiselyov, A. S. Tetrahedron Lett. 1999, 40, 4119.
30. Zificsak, C. A.; Hlasta, D. J. Tetrahedron 2004, 60, 8991.
31. (a) Heine, D. W.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427.
32. (b) Knaoka, Y.; Hamada, T.; Yonemitsu, O. Chem. Pharm. Bull. 1970, 18, 587.
33. Terashima, M.; Ishii, M.; Kanaoka, Y. Synthesis 1982, 484.
34. Cho, C. S.; Kim, D. T.; Zhang, J. Q.; Ho, S.-L.; Kim, T.-J.; Shim, S. C. J. Heterocycl. Chem. 2002, 39, 421.
35. Lidstorm, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 54, 9225.
36. (a) Yildiz-Oren, I.; Yalcin, I.; Aki-Sener, E.; Ucarturk, N. Eur. J. Med. Chem. 2004, 39, 291.
37. (b) Verma, M.; Tripathi, M.; Saxena, A. K.; Shanker, K. Eur. J. Med. Chem. 1994, 29, 941.
38. (c) Yalcin, ; Ören, ; Sener, E.; Akin, A.; Ucartürk, N. Eur. J. Med. Chem. 1992, 27, 401.
39. The work cited under ref. 14c deals with only three examples of benzoxazole formation by microwave-assisted condensation of aromatic carboxylic acids with 2-aminophenol.
40. Garrett, R. L. In Designing Safer Chemicals; Garrett, R. L.; De Vito, S. C., Eds.; American Chemical Society Symposium Series 640: Washington DC, 1996, Chap. 1.