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Samarium(III) triflate: a new catalyst for facile synthesis of benzothiazoles and benzoxazoles from carboxylic acids in aqueous media

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Abstract

A facile synthetic method for benzothiazoles and benzoxazoles comprising the reaction of corresponding 2-aminothiophenol and 2-aminophenol with various substituted aromatic carboxylic acids using Samarium(III) triflate as a catalyst has been described. The advantages of the method are short reaction times and aqueous reaction media and easy work-up. The catalysts can be recovered for the subsequent reactions and reused without any appreciable loss of efficiency.

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References

  1. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, M.F. Stevens, J. Med. Chem. 44, 1446 (2001)

    Article  CAS  Google Scholar 

  2. S. Aiello, G. Wells, E.L. Stone, H. Kadri, R. Bazzi, D.R. Bell, M.F. Stevens, C.S. Matthews, T.D. Bradshaw, A.D. Westwell, J. Med. Chem. 51, 5135 (2008)

    Article  CAS  Google Scholar 

  3. B.S. Tan, K.H. Tiong, A. Muruhadas, N. Randhawa, H.L. Hoo, T.D. Bradshaw, M.F. Stevens, O. Leong, Mol. Cancer Ther. 10, 1982 (2011)

    Article  CAS  Google Scholar 

  4. K. Wang, F.P. Guengerich, Chem. Res. Toxicol. 25, 1740 (2012)

    Article  CAS  Google Scholar 

  5. K. Serdons, C. Terwinghe, P. Vermaelen, K. Van Laere, H. Kung, L. Mortelmans, G. Bormans, A. Verbruggen, J. Med. Chem. 52, 1428 (2009)

    Article  CAS  Google Scholar 

  6. P.S. Yadav, D. Devprakash, G.P. Senthilkumar, Int. J. Pharm. Sci. Drug. Res. 1, 01 (2011)

    Google Scholar 

  7. D. Li, H. Zhang, C. Wang, S. Huang, J. Guo, Y. Wang, J. Mater. Chem. 22, 4319 (2012)

    Article  CAS  Google Scholar 

  8. R. Hu, J. Feng, D. Hu, S. Wang, S. Li, Y. Li, G. Yang, Angew. Chem. Int. Ed. 49, 4915 (2010)

    Article  CAS  Google Scholar 

  9. J.P. Davidson, E.J. Corey, J. Am. Chem. Soc. 125, 13486 (2003)

    Article  CAS  Google Scholar 

  10. J.A. Glober, G. Dornadula, M.R. Rice, A.L. Simcoe, D.J. Hazuda, M.D.J. Miller, J. Biol. Chem. 282, 8005 (2007)

    Article  Google Scholar 

  11. M. Ueki, K. Ueno, S. Miyadoh, K. Abe, K. Shibata, M. Taniguchi, S. Oi, J. Antibiot. 46, 1089 (1993)

    Article  CAS  Google Scholar 

  12. J. Jiang, X. Tang, W. Dou, H. Zhang, W. Liu, C. Wang, J. Zheng, J. Inorg. Biochem. 104, 583 (2010)

    Article  CAS  Google Scholar 

  13. P.D. Edwards, M.A. Zottola, M. Davis, J. Williams, P.A. Tuthill, J. Med. Chem. 38, 3972 (1995)

    Article  CAS  Google Scholar 

  14. A.B. Naidu, G. Sekar, Synthesis, 579 (2010)

  15. I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. West well, M.F.G. Stevens, J. Med. Chem. 45, 744 (2002)

    Article  CAS  Google Scholar 

  16. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III, (Elsevier, Oxford, 2008), Vol. 4, pp. 487–543

  17. Y.H. So, J.P. Heeschen, J. Org. Chem. 62, 3552 (1997)

    Article  CAS  Google Scholar 

  18. D.S. Bose, M. Idrees, Synthesis, 398 (2010)

  19. M. Lamani, K.R. Prabhu, J. Org. Chem. 76, 7938 (2011)

    Article  CAS  Google Scholar 

  20. A.J. Blacker, M.F. Mohamed, S.P. Marsden, O. Saidi, J.M.J. Williams, Tetrahedron Lett. 50, 6106 (2009)

    Article  CAS  Google Scholar 

  21. R.-G. Xing, Y.-N. Li, Q. Liu, Q.-Y. Meng, J. Li, X.-X. Shen, Z. Liu, B. Zhou, X. Yao, Z.-L. Liu, Eur. J. Org. Chem. 6627 (2010)

  22. R.S. Pottorf, N.K. Chadha, M. Katkevics, V. Ozola, E. Suna, H. Ghane, T. Regberg, M.R. Player, Tetrahedron Lett. 44, 175 (2003)

    Article  CAS  Google Scholar 

  23. R.H. Tale, Org. Lett. 4, 1641 (2002)

    Article  CAS  Google Scholar 

  24. S. Mourtas, D. Gatos, K. Barlos, Tetrahedron Lett. 42, 2201 (2001)

    Article  CAS  Google Scholar 

  25. A.K. Chakraborti, C. Selvam, G. Kaur, S. Bhagat, Synlett, 851 (2004)

  26. C.P. Chen, Y.J. Chen, Tetrahedron Lett. 45, 113 (2004)

    Article  CAS  Google Scholar 

  27. J.A. Seijas, M.P. Vazquez-Tato, M.R. Carballido-Reboredo, J. Crecente-Campo, L. Romar-Lopez, Synlett, 313 (2007)

  28. I.R. Laskar, T.M. Chen, Chem. Mater. 16, 111 (2004)

    Article  CAS  Google Scholar 

  29. R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Mol. Catal. A: Chem. 214, 155 (2004)

    Article  CAS  Google Scholar 

  30. H. Matsushita, S.H. Lee, M. Joung, B. Clapham, K.D. Janda, Tetrahedron Lett. 45, 313 (2004)

    Article  CAS  Google Scholar 

  31. X.L. Yang, C.M. Xu, S.M. Lin, J.X. Chen, J.C. Ding, H.Y. Wu, W.K. Su, J. Braz. Chem. Soc. 21, 37 (2010)

    Article  CAS  Google Scholar 

  32. K. Bahrami, M.M. Khodaei, F. Naali, J. Org. Chem. 73, 6835 (2008)

    Article  CAS  Google Scholar 

  33. H.Y. Guo, J.C. Li, Y.L. Shang, Chin. Chem. Lett. 20, 1408 (2009)

    Article  CAS  Google Scholar 

  34. M. Okimoto, T. Yoshida, M. Hoshi, K. Hattori, M. Komata, K. Tomozawa, T. Chiba, Heterocycles 75, 35 (2008)

    Article  CAS  Google Scholar 

  35. A. Kumar, R.A. Maurya, P. Ahmad, J. Comb. Chem. 11, 198 (2009)

    Article  CAS  Google Scholar 

  36. H.L. Xiao, J.X. Chen, M.C. Liu, D.J. Zhu, J.C. Ding, H.Y. Wu, Chem. Lett. 38, 170 (2009)

    Article  CAS  Google Scholar 

  37. M. Abdollahi-Alibeik, S. Poorirani, Phosphorus, Sulfur Silicon Relat. Elem. 184, 3182 (2009)

    Article  CAS  Google Scholar 

  38. M. Kodomari, Y. Tamaru, T. Aoyama, Synth. Commun. 34, 3029 (2004)

    Article  CAS  Google Scholar 

  39. U.R. Pratap, J.R. Mali, D.V. Jawale, R.A. Mane, Tetrahedron Lett. 50, 1352 (2009)

    Article  CAS  Google Scholar 

  40. K. Bahrami, M.M. Khodaei, A. Nejatia, Green Chem. 12, 1237 (2010)

    Article  CAS  Google Scholar 

  41. A. Kumar, S. Sharma, R.A. Maurya, Tetrahedron Lett. 51, 6224 (2010)

    Article  CAS  Google Scholar 

  42. S.V. Nalage, S.V. Bhosale, D.S. Bhosale, W.N. Jadhav, Chin. Chem. Lett. 21, 790 (2010)

    Article  CAS  Google Scholar 

  43. H. Eshghi, M. Rahimizadeh, A. Shiri, P. Sedaghat, Bull. Korean Chem. Soc. 33, 515 (2012)

    Article  CAS  Google Scholar 

  44. M.S. Mayo, X. Yu, X. Zhou, X. Feng, Y. Yamamoto, M. Bao, J. Org. Chem. 79, 6310 (2014)

    Article  CAS  Google Scholar 

  45. M.S. Mayo, X. Yu, X. Zhou, X. Feng, Y. Yamamoto, M. Bao, Org. Lett. 16, 764 (2014)

    Article  CAS  Google Scholar 

  46. C.-J. Li, B.M. Trost, Proc. Natl. Acad. Sci. USA 105, 13197 (2008)

    Article  CAS  Google Scholar 

  47. A.V. Narsaiah, A.R. Reddy, J.S. Yadav, Synth. Commun. 41, 262 (2011)

    Article  CAS  Google Scholar 

  48. S. Kobayashi, K. Manabe, Acc. Chem. Res. 35, 209 (2002)

    Article  CAS  Google Scholar 

  49. A. Dzudza, T.J. Marks, J. Org. Chem. 73, 4004 (2008)

    Article  CAS  Google Scholar 

  50. A.V. Narsaiah, A.R. Reddy, J.S. Yadav, Synth. Commun. 41, 2794 (2011)

    Article  CAS  Google Scholar 

  51. P.B. Gorepatil, Y.D. Mane, V.S. Ingle, Synlett 24, 2241 (2013)

    Article  CAS  Google Scholar 

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Acknowledgment

One of the authors, Mr. P.B. Gorepatil, is grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi for a Junior Research Fellowship (JRF).

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Authors and Affiliations

  1. Department of Chemistry, S. C. S. College, Omerga, Dist-Osmanabad, 413 606, India

    Pratapsinha B. Gorepatil, Yogesh D. Mane & Vilas S. Ingle

  2. Department of Chemistry, S. G. R. G. S. College, Paranda, Dist-Osmanabad, India

    Amarsinha B. Gorepatil

  3. Department of Chemistry, B. P. C. A. S. Angar, Dist-Solapur, 413 214, India

    Mahadev V. Gaikwad

Authors
  1. Pratapsinha B. Gorepatil
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  2. Yogesh D. Mane
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  3. Amarsinha B. Gorepatil
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  4. Mahadev V. Gaikwad
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  5. Vilas S. Ingle
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Correspondence to Vilas S. Ingle.

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Gorepatil, P.B., Mane, Y.D., Gorepatil, A.B. et al. Samarium(III) triflate: a new catalyst for facile synthesis of benzothiazoles and benzoxazoles from carboxylic acids in aqueous media. Res Chem Intermed 41, 8355–8362 (2015). https://doi.org/10.1007/s11164-014-1897-x

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  • DOI: https://doi.org/10.1007/s11164-014-1897-x

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