Efficient synthesis of 2-(2′-hydroxyphenyl)benzoxazole by palladium(II)-catalyzed oxidative cyclization

Tetrahedron Letters

Volumn 50, Issue 48, 2009, Pages 6680-6683

  Chen, Wei Hua ^a   Pang, Yi ^a  

^a UNIVERSITY OF AKRON   (United States)

Author keywords

Benzoxazole; Oxidative cyclization; Palladium catalyst; Schiff base

Indexed keywords

2 (2' HYDROXYPHENYL)BENZOXAZOLE; 2 AMINOPHENOL; ALDEHYDE DERIVATIVE; BENZOXAZOLE DERIVATIVE; MANGANESE DIOXIDE; PALLADIUM; SCHIFF BASE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; OXIDATION; POLYMERIZATION;

EID: 70349773084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.084     Document Type: Article

References (33)

1. Williams D.L., and Heller A. J. Phys. Chem. 74 (1970) 4473-4480
2. Taki M., Wolford J.L., and O'Halloran T.V. J. Am. Chem. Soc. 126 (2004) 712-713
3. Ohshima A., Momotake A., and Arai T. Tetrahedron Lett. 45 (2004) 9377-9381
4. Chu Q., Medvetz D.A., and Pang Y. Chem. Mater. 19 (2007) 6421-6429
5. Vazquez S.R., Rodriguez M.C.R., Mosquera M., and Rodriguez-Prieto F. J. Phys. Chem. A 111 (2007) 1814-1826
6. KcKee M.L., and Kerwin S.M. Bioorg. Med. Chem. 16 (2008) 1775-1783
7. Kusumi T., Ooi T., Walchli M.R., and Kakisawa H. J. Am. Chem. Soc. 110 (1988) 2954-2958
8. Rodriguez C., Groot N.S., Rimola A., Alvarez-Larena A., Lloveras V., Vidal-Gancedo J., Ventura S., Vendrell J., Sodupe M., and Gonzalez-Duarte P. J. Am. Chem. Soc. 131 (2009) 1436-1451
9. Terashima M., and Ishii M. Synthesis (1982) 484-485 and references cited therein
10. Hein D.W., Alheim R.J., and Leavitt J.J. J. Am. Chem. Soc. 79 (1957) 427-429
11. So Y.H., and Heeschen J.P. J. Org. Chem. 62 (1997) 3552-3561
12. Chang J., Zhao K., and Pan S. Tetrahedron Lett. 43 (2002) 951-954
13. Ohshima A., Lkegami M., Shinohara Y., Momotake A., and Arai T. Bull. Chem. Soc. Jpn. 80 (2007) 561-566
14. Asada H., Ozeki M., Fujiwara M., and Matsushita T. Polyhedron 21 (2002) 1139-1148
15. Praveen C., Kumar K.H., Muralidharan D., and Perumal P.T. Tetrahedron 64 (2008) 2369-2374
16. Vinsova J., Cermakova K., Tomeckova A., Ceckova M., Jampilek J., Cermak P., Kunes J., Dolezale M., and Staud F. Bioorg. Med. Chem. 14 (2006) 5850-5865
17. Liao C.-H., Wang C.-S., Sheu H.-S., and Lai C.K. Tetrahedron 64 (2008) 7977-7985
18. Chen Y., and Zeng D.X. J. Org. Chem. 69 (2004) 5037-5040
19. Talapatra S.K., Chaudhuri P., and Talapatra B. Heterocycles 14 (1980) 1279-1282
20. Ohshima A., Momotake A., Nagahata R., and Arai T. J. Phys. Chem. A 109 (2005) 9731-9736
21. Seo J., Kim S., Lee Y.-S., Kwon O.-H., Park K.H., Choi S.Y., Chung Y.K., Jang J., and Park S.Y. J. Photochem. Photobiol. A 191 (2007) 51-58
22. Blacker A.J., Farah M.M., Hall M.I., Marsden S.P., Saidi O., and Williams J.M.J. Org. Lett. 11 (2009) 2039-2042
23. Speier G. J. Mol. Catal. 41 (1987) 253-260
24. Chen Y.-X., Qian L.-F., Zhang W., and Han B. Angew. Chem., Int. Ed. 47 (2008) 9330-9333
25. Tsuji J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis (1997), Wiley, New York
26. Choudary B.M., Reddy N.P., Kantam M.L., and Jam Z. Tetrahedron Lett. 26 (1985) 6257-6258
27. Muzart J. Tetrahedron 59 (2003) 5789-5816
28. Sridharan V., Muthusubramanian S., and Sivasubramanian S. Magn. Reson. Chem. 41 (2003) 291-295
29. 4, 334.9667; found, 334.9787.
30. Fossey J., and Richards C.J. Organometallics 21 (2002) 5259-5264
31. 3, 300 MHz) δ = 8.78 (s, 2H), 7.79 (s, 2H), 7.04 (d, 2H, J = 7.8 Hz), 6.90 (t, 2H, J = 7.8 Hz), 6.76 (d, 2H, J = 7.8 Hz), 6.65 (t, 2H, J = 7.8 Hz).
32. 3, 300 MHz) δ = 12.22 (s, 1H), 10.5 (s, 1H, CHO), 8.38 (s, 1H), 8.03 (s, 1H), 7.78 (m, 1H), 7.64 (m, 1H), 7.44 (m, 2H).
33. Simandi L.I., Barna T.M., Korecz L., and Rockenbauer A. Tetrahedron Lett. 34 (1993) 717-720