Direct and efficient conversion of thioamides to benzazole derivatives using N,N'-dibromophenytoin

Document Type : Original Article

Authors

1 Department of Chemistry, University of Isfahan, Iran

2 Department of Chemistry, University of Isfahan

Abstract

A novel and efficient method has been developed for preparation of benzoxazole, benzimidazole and benzthioazole via one-pot condensation of N,N'-disubstituted thioamides with 2-aminophenol, 2-aminothiophenol, and 1,2-diaminobenzene using N,N'-dibromo phenytoin as a mild oxidant. Hence, thioamides were reacted with 2-aminophenol, 2-aminothiophenol, and 1,2-diaminobenzene respectively in the presence of N,N'-dibromo phenytoin in DMF to produce benzoxazole, benzimidazole and benzthioazole derivatives in moderate to good yields. Possibility of synthesis of three different heterocycles which have important industrial, agricultural, and biological applications, is one of the advantages of the presented method. Performing the reaction under very mild temperature and in short time is still another merit of the current method.

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References

[1] D. Kumar, M.R. Jacob, M.B. Reynolds, S.M. Kerwin, Bioorg. Med. Chem. 10 (2002) 3997.
[2] I. Yildiz-Oren, I. Yalcin, E. Aki-Sener, N. Ucarturk, Eur. J. Med. Chem. 39 (2004) 291.
[3] X. Song, B.S. Vig, P.L. Lorenzi, J.C. Drach, L.B. Townsend, G.L. Amidon, J. Med. Chem. 48 (2005) 1274.
[4] N. Mars, M. Kocevar, Helv. Chim. Acta. 10 (2011)1860.
[5] R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Mol. Catal A: Chem. 214 (2004) 155.
[6] D.W. Hein, R.J. Alheim, J.J. Leavitt, J. Am. Chem. Soc. 79 (1957) 427.
[7] G.L. Jenkins, A.M. Knevel, C.S. Davis, J. Org. Chem. 26 (1961) 274.
[8] M. Terashima, M. Ishii, Synthesis 1982, 484.
[9] A.K. Chakraborti, S. Rudrawar, G. Kaur, L. Sharma, Synlett 1533 (2004).
[10] K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73 (2008) 6835.
[11] H. Zali Boeini, K. Hajibabaei Najafabadi, Eur. J. Org. Chem. 29 (2009) 4926.
[12] T.D. Waugh, R.C. Waugh, GB Patent, (1963) 933531.
[13] F. Matloubi Moghadam, H. Zali Boeini, Synlett  10 (2005) 1612.
[14] H. Zali Boeini, S.G. Mansouri, Synth. Commun. 45 (2015) 1681.
[15] H. Zali Boeini, Synth. Commun. 41 (2011) 2932.
[16] S. Ueda, H. Nagasawa, Angew.Chem. Int. Ed. 47 (2008)6411.
[17] J.M. Khurana-Sneha, V. K. Kanika, Synth. Commun. 42 (2012) 2606.
[18] S. Kamble, G. Rashinkar, A. Kumbhar, R. Salunkhe, Synth. Commun. 42 (2012) 756.
[19] D.Q. Shi, G.L. Dou, S.F. Rong, Synth. Commun. 40 (2010) 2302.
[20] A.D. Jordan, C. Luo, A.B. Reitz, J. Org. Chem. 68 (2003) 8693.
Applied Chemistry Today
Volume 14, Issue 50
April 2019
Pages 105-112

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