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Agar: a novel, efficient, and biodegradable catalyst for the one-pot three-component and green synthesis of 2,3-dihydroquinazolin-4(1H)-one, 4H-pyrimidobenzothiazole and 2-aminobenzothiazolomethylnaphthol derivatives

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Abstract

3-(2′-Benzothiazolyl)-2,3-dihydroquinazolin-4(1H)- one, 1-((benzo[d]thiazol-2-ylamino) (aryl)-methyl)naphthalen-2-ol and 4H-pyrimido[2,1-b][1,3]benzothiazoles derivatives were prepared via one-pot three-component reaction of arylaldehydes, 2-aminobenzothiazole and isatoic anhydride or β-naphthol or ethyl/methyl acetoacetate in the presence of agar as a highly efficient homogenous catalyst. The use of a non-toxic and biodegradable catalyst, as well as high yields, short reaction time, simple work-up and green conditions are the most important advantages of this method.

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References

  1. K. Niknam, N. Borazjani, R. Rashidian, A. Jamali, Chin. J. Catal. 34, 2245 (2013)

    Article  CAS  Google Scholar 

  2. A. Kumar, M.K. Gupta, M. Kumar, Green Chem. 14, 290 (2012)

    Article  CAS  Google Scholar 

  3. C. Hulme, V. Gore, Curr. Med. Chem. 10, 51 (2003)

    Article  CAS  Google Scholar 

  4. T.A. Martin, A.G. Wheller, R.F. Majewski, J.R. Corrigan, J. Med. Chem. 7, 812 (1964)

    Article  CAS  Google Scholar 

  5. S.L. Cao, Y.P. Feng, Y.Y. Jiang, S.Y. Liu, G.Y. Ding, R.T. Li, Bioorg. Med. Chem. Lett. 15, 1915 (2005)

    Article  CAS  Google Scholar 

  6. R.P. Maskey, M. Shaaban, I. Grun-Wollny, H.J. Laatsch, Nat. Prod. 67, 1131 (2004)

    Article  CAS  Google Scholar 

  7. Y.H. Na, S.H. Hong, J.H. Lee, W.K. Park, D.J. Baek, H.Y. Koh, Y.S. Cho, H. Choo, Bioorg. Med. Chem. 16, 2570 (2008)

    Article  CAS  Google Scholar 

  8. R. Williams, C.M. Niswender, Q. Luo, U. Le, P.J. Conn, C.W. Lindsley, Med. Chem. Lett. 19, 962 (2009)

    Article  CAS  Google Scholar 

  9. Z.H. Zhang, H.Y. Lu, S.H. Yang, J.W. Gao, J. Comb. Chem. 12, 643 (2010)

    Article  CAS  Google Scholar 

  10. A. Safar-Teluri, S. Bolouk, Monatsh. Chem. 141, 1113 (2010)

    Article  Google Scholar 

  11. M.J. Hour, L.J. Huang, S.C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K.H. Lee, J. Med. Chem. 43, 4479 (2000)

    Article  CAS  Google Scholar 

  12. M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgarya, A. Mohammadi, Tetrahedron Lett. 46, 6123 (2005)

    Article  CAS  Google Scholar 

  13. J.X. Chen, D. Wu, F. He, M.C. Liu, H.J. Wu, C. Ding, W.K. Su, Tetrahedron Lett. 49, 3814 (2008)

    Article  CAS  Google Scholar 

  14. M.P. Surpur, P.R. Single, S.B. Patil, S.D. Samat, Synth. Commun. 37, 1965 (2007)

    Article  CAS  Google Scholar 

  15. P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth. Commun. 36, 2287 (2006)

    Article  CAS  Google Scholar 

  16. L.M. Wang, L. Shao, J.H. Hu, T. Yu, L. Zhang, J. Fluor. Chem. 129, 1139 (2008)

    Article  CAS  Google Scholar 

  17. J.X. Chen, W.K. Su, H.Y. Wu, M.C. Liu, C. Jin, Green Chem. 9, 972 (2007)

    Article  CAS  Google Scholar 

  18. A. Shaabani, A. Rahmati, R. Moghimi, J. C. R. Chin 11, 759 (2008)

    CAS  Google Scholar 

  19. B. Bararjanian, S. Balalaie, B. Movassagh, H.R. Bijanzadeh, Tetrahedron Lett. 51, 3277 (2010)

    Article  CAS  Google Scholar 

  20. P. Walden, Bull. Rus. Acad. Sci. Key: citeulike:12856962, 405, (1914)

  21. K.N. Marsh, J.A. Boxall, R. Lichtenthaler, Fluid Phase Equilib. 219, 93 (2004)

    Article  CAS  Google Scholar 

  22. H.R. Shaterian, A.R. Oveisi, M. Honarmand, Synth. Commun. 40, 1231 (2010)

    Article  CAS  Google Scholar 

  23. P.K. Sahu, S.K. Gupta, D.D. Agarwal, Ind. Eng. Chem. Res. 53, 2085 (2014)

    Article  CAS  Google Scholar 

  24. S. Shinde, G. Rashinkar, R. Salunkhe, J. Mol. Liq. 178, 122 (2013)

    Article  CAS  Google Scholar 

  25. N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35, 1 (2014)

    Article  Google Scholar 

  26. H.R. Shaterian, F. Rigi, Res. Chem. Intermed. (2013)

  27. E. Balfour, Cyclopedia of India and of eastern and southern Asia, commercial, industrial and scientific: useful arts and manufactures. Scottish and Adelphi Presses, p. 50 (1871)

  28. A. Davidson, The Oxford Companion to Food, (2006)

  29. W. Peter, P. Glyn, Handbook of hydrocolloids. Cambridge: Woodhead. Chapter 2: Agar, p. 28 (2000)

  30. S. Chandrasekhar, K. Johny, C.R. Reddy, Tetrahedron: Asymm, 20, 1742, (2009)

  31. M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Moradi, N. Hazeri, A. Davodi, S.S. Sajadikhah, Tetrahedron 67, 8492 (2011)

    Article  CAS  Google Scholar 

  32. M.R. Mousavi, N. Hazeri, M.T. Maghsoodlou, S. Salahi, S.M. Habibi-Khorassani, Chin. Chem. Lett. 24, 411 (2013)

    Article  CAS  Google Scholar 

  33. N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, J. Chem. Res. 37, 550 (2013)

  34. L. Wu, E-J. Chem. 9, 739 (2012)

    Article  CAS  Google Scholar 

  35. N.G. Khaligh, Tetrahedron Lett. 53, 1637 (2012)

    Article  CAS  Google Scholar 

  36. S. Javanshir, A. Ohanian, M. Heravi, M.R. Naimi-Jamal, F. Bamoharram, J. Saudi Chem. Soc. 10, 13 (2011)

    Google Scholar 

  37. Y. Yi, G. Hong-Yun, Chin. J. Org. Chem. 31, 96 (2011)

    Google Scholar 

  38. A. Shaabani, A. Rahmati, E. Farhangi, Tetrahedron Lett. 48, 7291 (2007)

    Article  CAS  Google Scholar 

  39. A. Kumar, M.S. Rao, V.K. Rao, Aust. J. Chem. 63, 1538 (2010)

    Article  CAS  Google Scholar 

  40. A. Shaabani, A. Rahmati, S. Nad, Bioorg. Med. Chem. Lett. 15, 5553 (2005)

    Article  CAS  Google Scholar 

  41. X.S. Wang, G.S. Yang, G. Zhao, Tetrahedron Asymmetry 19, 709 (2008)

    Article  CAS  Google Scholar 

  42. A.B. Atar, Y.T. Jeong, Mol. Divers. 18, 389, (2014)

  43. L. Nagarapu, H.K. Gaikwad, J.D. Palem, R. Venkatesh, R. Bantu, B. Sridhar, Synth. Commun. 43, 93 (2013)

    Article  CAS  Google Scholar 

  44. P.K. Sahu, R. Jain, R. Yadava, D.D. Agarwal, Catal. Sci. Technol. 2, 2465 (2012)

    Article  CAS  Google Scholar 

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Acknowledgment

We are grateful to the University of Sistan and Baluchestan Research Council for the partial support of this research.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran

    Ashraf Moradi, Reza Heydari & Malek Taher Maghsoodlou

Authors
  1. Ashraf Moradi
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  2. Reza Heydari
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  3. Malek Taher Maghsoodlou
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Correspondence to Reza Heydari.

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Moradi, A., Heydari, R. & Maghsoodlou, M.T. Agar: a novel, efficient, and biodegradable catalyst for the one-pot three-component and green synthesis of 2,3-dihydroquinazolin-4(1H)-one, 4H-pyrimidobenzothiazole and 2-aminobenzothiazolomethylnaphthol derivatives. Res Chem Intermed 41, 7377–7391 (2015). https://doi.org/10.1007/s11164-014-1818-z

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  • DOI: https://doi.org/10.1007/s11164-014-1818-z

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