Tin(II) chloride-mediated synthesis of 2-substituted benzoxazoles
Corresponding Author
Chan Sik Cho
Research Institute of Industrial Technology, Kyungpook National University, Taegu 702-701, Korea
Chan Sik Cho, Research Institute of Industrial Technology, Kyungpook National University, Taegu 702-701, Korea
Sang Chul Shim, Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorDong Tak Kim
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorJiao Qiang Zhang
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorSon-Lam Ho
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorTae-Jeong Kim
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorCorresponding Author
Sang Chul Shim
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Chan Sik Cho, Research Institute of Industrial Technology, Kyungpook National University, Taegu 702-701, Korea
Sang Chul Shim, Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorCorresponding Author
Chan Sik Cho
Research Institute of Industrial Technology, Kyungpook National University, Taegu 702-701, Korea
Chan Sik Cho, Research Institute of Industrial Technology, Kyungpook National University, Taegu 702-701, Korea
Sang Chul Shim, Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorDong Tak Kim
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorJiao Qiang Zhang
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorSon-Lam Ho
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorTae-Jeong Kim
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorCorresponding Author
Sang Chul Shim
Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Chan Sik Cho, Research Institute of Industrial Technology, Kyungpook National University, Taegu 702-701, Korea
Sang Chul Shim, Department of Industrial Chemistry, College of Engineering, Kyungpook National University, Taegu 702-701, Korea
Search for more papers by this authorAbstract
2-Aminophenols react with an array of carboxylic acids in dioxane at 180° in the presence of tin(II) chloride to afford the corresponding 2-substituted benzoxazoles in good yields. The reaction is applicable to a wide range of alkyl, alkenyl, aryl carboxylic acids.
References and Notes
- 1 D. W. Heine, R. J. Alheim and J. J. Leavitt, J. Am. Chem. Soc., 79, 427 (1957).
- 2 Y. Kanaoka, T. Hamada and O. Yonemitsu, Chem. Pharm. Bull., 18, 587 (1970).
- 3 M. Terashima, M. Ishii and Y. Kanaoka, Synthesis, 484 (1982).
- 4 K. Nakagawa, H. Onoue and J. Sugita, Chem. Pharm. Bull., 12, 1135 (1964).
- 5 T. Kondo, S. Yang, K.-T. Huh, M. Kobayashi, S. Kotachi and Y. Watanabe, Chem. Lett., 1275 (1991).
- 6 R. J. Perry, B. D. Wilson and R. J. Miller, J. Org. Chem., 57, 2883 (1992).
- 7 R. J. Perry and B. D. Wilson, J. Org. Chem., 57, 6351 (1992).
- 8 C. S. Cho, H. K. Lim, S. C. Shim, T. J. Kim and S. C. Shim, Chem. Commun., 995 (1998).
- 9 C. S. Cho, J. H. Kim and S. C. Shim, Tetrahedron Lett., 41, 1811 (2000).
- 10 C. S. Cho, J. H. Kim, T.-J. Kim and S. C. Shim, Tetrahedron, 57, 3321 (2001).
- 11 C. S. Cho, T. K. Kim, S. W. Yoon, T.-J. Kim and S. C. Shim, Bull. Korean Chem. Soc., 22, 545 (2001).
- 12 C. S. Cho, B. H. Oh and S. C. Shim, Tetrahedron Lett., 40, 1499 (1999).
- 13 C. S. Cho, B. H. Oh and S. C. Shim, J. Heterocyclic Chem., 36, 1175 (1999).
- 14 C. S. Cho, B. H. Oh, S. C. Shim and D. H. Oh, J. Heterocyclic Chem., 37, 1315 (2000).
- 15 C. S. Cho, J. S. Kim, B. H. Oh, T.-J. Kim and S. C. Shim, Tetrahedron, 56, 7747 (2000).
- 16 C. S. Cho, B. H. Oh, J. S. Kim, T.-J. Kim and S. C. Shim, Chem. Commun., 1885 (2000).
- 17 C. S. Cho, T. K. Kim, T.-J. Kim, S. C. Shim and N. S. Yoon, J. Heterocyclic Chem., in press.
- 18 C. S. Cho, J. S. Kim, H. S. Kim, T.-J. Kim and S. C. Shim, Synth. Commun., 32, 3791 (2001).
- 19 G. L. Tullos, J. M. Powers, S. J. Jeskey and L. J. Mathias, Macromolecules, 32, 3598 (1999).
- 20 M. I. El-Sheikh, A. Marks and E. R. Biehl, J. Org. Chem., 46, 3256 (1981).
- 21 E. Tauer and K. H. Grellmann, J. Org. Chem., 46, 4252 (1981).
- 22 R. S. Varma and D. Kumar, J. Heterocyclic Chem., 35, 1539 (1998).