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Lithium bromide catalyzed efficient and convenient synthesis of 2-arylbenzothiazole derivatives

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Abstract

A new and efficient protocol was developed for synthesis of benzothiazoles using lithium bromide as catalyst under environmentally friendly conditions. The developed synthetic protocol represents a novel and very simple route for preparation of 2-substituted benzothiazole derivatives. In addition, an ultrasound irradiation technique is successfully implemented for carrying out the reactions in shorter reaction times.

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References

  1. C.A. Mathis, Y. Wang, D.P. Holt, G.F. Huang, M.L. Debnath, W.E. Klunk, J. Med. Chem. 46, 2740 (2003)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. D. Alagille, R.M. Baldwin, G.D. Tamagnan, Tetrahedron Lett. 46, 1349 (2005)

    Article  CAS  Google Scholar 

  4. M.F.G. Stevens, G. Wells, A.D. Westwell, T.D. Poole, Chem. Abstr. 138, 106698 (2003)

    Google Scholar 

  5. R. Caujolle, P. Loiseau, M. Payard, P. Gayral, M.N. Kerhir, Ann. Pharm. Fr. 47, 68 (1989)

    CAS  Google Scholar 

  6. K. Yamamoto, M. Fujita, K. Tabashi, Y. Kawashima, E. Kato, M. Oya, T. Iso, J. Iwao, J. Med. Chem. 31, 919 (1988)

    Article  CAS  Google Scholar 

  7. H. Yoshida, R. Nakao, H. Nohta, M. Yamaguchi, Dyes Pigments 47, 239 (2000)

    Article  CAS  Google Scholar 

  8. I. Petkov, T. Deligeorgiev, P. Markov, M. Evstatiev, S. Fakirov, Polym. Degrad. Stab. 33, 53 (1991)

    Article  CAS  Google Scholar 

  9. S.P.G. Costa, R.M.F. Batista, P. Cardoso, M. Belsley, M.M.M. Raposo, Eur. J. Org. Chem. 17, 3938 (2006)

    Article  Google Scholar 

  10. J.C. Day, L.C. Tisi, M.J. Bailey, Luminescence 19, 8 (2004)

    Article  CAS  Google Scholar 

  11. R.M.F. Batista, S.P.G. Costa, M.M.M. Raposo, Tetrahedron Lett. 45, 2825 (2004)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. T. Itoh, K. Nagata, H. Ishikawa, A. Ohsawa, Heterocycles 62, 197 (2004)

    Article  CAS  Google Scholar 

  15. Y. Li, Y.L. Wang, J.Y. Wang, Chem. Lett. 35, 460 (2006)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  18. N. Azizi, A.K. Amiri, R. Baghi, M. Bolourtchian, M.M. Hashemi, Monatsh. Chem. 140, 1471 (2009)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. C.B. Mukhopadhyay, A. Datta, J. Heterocycl. Chem. 46, 91 (2009)

    Article  CAS  Google Scholar 

  22. L.J. Zhang, J. Xia, Y.Q. Zhou, H. Wang, S.W. Wang, Synth. Commun. 42, 328 (2012)

    Article  CAS  Google Scholar 

  23. S. Sadjadi, H. Sepehrian, Ultrason. Sonochem. 18, 480 (2011)

    Article  CAS  Google Scholar 

  24. G.F. Chen, H.M. Jia, L.Y. Zhang, B.H. Chen, J.T. Li, Ultrason. Sonochem. 20, 627 (2013)

    Article  CAS  Google Scholar 

  25. R. Fazaeli, H. Aliyan, Appl. Catal. A Gen. 353, 74 (2009)

    Article  CAS  Google Scholar 

  26. D.K. Yadav, R. Patel, V.P. Srivastava, G. Watal, L.D.S. Yadav, Chin. J. Chem. 29, 118 (2011)

    Article  CAS  Google Scholar 

  27. D.V. Dekhane, S.S. Pawar, S.V. Gupta, M.S. Shingare, S.N. Thore, Chin. Chem. Lett. 21, 519 (2010)

    Article  CAS  Google Scholar 

  28. H. Firouzabadi, N. Iranpoor, B. Karimi, Synthesis 1, 58 (1999)

    Article  Google Scholar 

  29. T.J. Mason, D. Peters, Practical Sonochemistry, 2nd edn. (Ellis Horwood, London, 2002)

    Book  Google Scholar 

  30. R.S. Joshi, P.G. Mandhane, S.D. Diwakar, C.H. Gill, Ultrason. Sonochem. 17, 298 (2010)

    Article  CAS  Google Scholar 

  31. G.R. Jadhav, M.U. Shaikh, R.P. Kale, C.H. Gill, Chin. Chem. Lett. 20, 535 (2009)

    Article  CAS  Google Scholar 

  32. S.K. Dabhade, R.O. Bora, M. Farooqui, C.H. Gill, Chin. Chem. Lett. 20, 893 (2009)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors are grateful to the Head, Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad for providing the laboratory facility, and M.D.N. thanks the Council of Scientific and Industrial Research, New Delhi for providing a senior research fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, Maharashtra, India

    Charansingh H. Gill, Mukesh D. Nikam, Pravin S. Mahajan, Asha V. Chate, Sanjay K. Dabhade & Pravin V. Badadhe

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  1. Charansingh H. Gill
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  2. Mukesh D. Nikam
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  3. Pravin S. Mahajan
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  4. Asha V. Chate
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Correspondence to Charansingh H. Gill.

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Gill, C.H., Nikam, M.D., Mahajan, P.S. et al. Lithium bromide catalyzed efficient and convenient synthesis of 2-arylbenzothiazole derivatives. Res Chem Intermed 41, 7509–7516 (2015). https://doi.org/10.1007/s11164-014-1840-1

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  • DOI: https://doi.org/10.1007/s11164-014-1840-1

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