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Nano-TiCl2/cellulose: an eco-friendly bio-based catalyst for one-pot synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives

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Abstract

Cellulose is among the most abundant natural carbon-based biopolymers containing free OH groups with nucleophilic character for bonding to Lewis acids such as TiCl4. Nano-TiCl2/cellulose as a bio-based and eco-friendly Lewis acid catalyst was prepared via reaction of nano-cellulose and TiCl4 in dichloromethane as solvent under room temperature conditions. This catalyst has been characterized by Fourier transform infrared spectroscopy, field emission scanning electron microscopy, powder X-ray diffraction, energy dispersive X-ray spectroscopy, X-ray fluorescence techniques, and transmission electron microscopy. Nano-TiCl2/cellulose has been shown to effectively promote multi-component synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives by reaction of aldehydes, β-ketoester, and 2-amino benzothiazole under thermal conditions in polyethylene glycol 400 as solvent. Simple methodology,an eco-friendly catalyst, a clean procedure, easy work-up, and excellent yields are some of the important advantages of this protocol.

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References

  1. A.D. Borthwick, D.E. Davies, P.F. Ertl, A.M. Exall, T.M. Haley, G.J. Hart, D.L. Jackson, N.R. Parry, A. Patikis, N. Trivedi, J. Med. Chem. 46, 4428 (2003)

    Article  CAS  Google Scholar 

  2. Q.-S. Fang, J. Zhou, Z.-B. Song, Res. Chem. Intermed. 42, 2035 (2016)

    Article  Google Scholar 

  3. S. Gupta, N. Ajmera, N. Gautam, R. Sharma, D. Gauatam, Ind. J. Chem. 48, 853 (2009)

    Google Scholar 

  4. R.M. Kumbhare, V. Ingle, Ind. J. Chem. 48, 996 (2009)

    Google Scholar 

  5. Y. Murthi, D. Pathak, J. Pharm. Res. 7, 153 (2008)

    Google Scholar 

  6. B. Rajeeva, N. Srinivasulu, S.M. Shantakumar, Eur. J. Chem 6, 775 (2009)

    CAS  Google Scholar 

  7. M.A. Mahran, S. William, F. Ramzy, A.M. Sembel, Molecules 12, 622 (2007)

    Article  CAS  Google Scholar 

  8. P. Sahu, P. Sahu, D. Thavaselvam, A. Alafeefy, D. Agarwal, Med. Chem. Res. 24, 725 (2015)

    Article  CAS  Google Scholar 

  9. D. Bhavsar, J. Trivedi, S. Parekh, M. Savant, S. Thakrar, A. Bavishi, A. Radadiya, H. Vala, J. Lunagariya, M. Parmar, Bioorg. Med. Chem. Lett. 21, 3443 (2011)

    Article  CAS  Google Scholar 

  10. D.R.S. Reddy, R.L. Priyadarshini, Der Pharma. Chem. 5, 207 (2013)

    CAS  Google Scholar 

  11. M. Yoshida, I. Hayakawa, N. Hayashi, T. Agatsuma, Y. Oda, F. Tanzawa, S. Iwasaki, K. Koyama, H. Furukawa, S. Kurakata, Y. Sugano, Bioorg. Med. Chem. Lett. 15, 3328 (2005)

    Article  CAS  Google Scholar 

  12. M.T. Gabr, N.S. El-Gohary, E.R. El-Bendary, M.M. El-Kerdawy, Eur. J. Med. Chem. 85, 576 (2014)

    Article  CAS  Google Scholar 

  13. M.A. El-Sherbeny, Arzneimittelforschung 50, 848 (2000)

    CAS  Google Scholar 

  14. A. Bartovič, D. Ilavský, O. Šimo, L. Zalibera, A. Belicová, M. Seman, Collect. Czech. Chem. Commun. 60, 583 (1995)

    Article  Google Scholar 

  15. D.V. Kashinath, Y.M. Rajmani, C.S. Ravindra, J. Pharm. Res. 6, 574 (2013)

    Google Scholar 

  16. M.M.M. Gineinah, Sci. Pharm. 69, 53 (2001)

    CAS  Google Scholar 

  17. I. Ćaleta, M. Grdiša, D. Mrvoš-Sermek, M. Cetina, V. Tralić-Kulenović, K. Pavelić, G. Karminski-Zamola, Il Farmaco 59, 297 (2004)

    Article  Google Scholar 

  18. M.S. Chaithanya, V.P. Vaidya, G. Nagendrappa, Asian J. Chem. 23, 1618 (2011)

    CAS  Google Scholar 

  19. P.K. Sahu, P.K. Sahu, S.K. Gupta, D. Thavaselvam, D.D. Agarwal, Eur. J. Med. Chem. 54, 366 (2012)

    Article  CAS  Google Scholar 

  20. S.G. Badne, D.K. Swamy, V.N. Bhosale, S.V. Kuberkar, J. Heterocycl. Chem. 48, 849 (2011)

    Article  CAS  Google Scholar 

  21. A.A. Pavlenko, K.S. Shikhaliev, A.Y. Potapov, D.V. Krylsky, Chem. Heterocycl. Compd. 41, 689 (2005)

    Article  CAS  Google Scholar 

  22. A. Shaabani, A. Rahmati, S. Naderi, Bioorg. Med. Chem. Lett. 15, 5553 (2005)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  25. P.K. Sahu, P.K. Sahu, Y. Sharma, D.D. Agarwal, J. Heterocycl. Chem. 51, 1193 (2014)

    Article  CAS  Google Scholar 

  26. M.M. Heravi, E. Hashemi, Y.S. Beheshtiha, K. Kamjou, M. Toolabi, N. Hosseintash, J. Mol. Catal. A Chem. 392, 173 (2014)

    Article  CAS  Google Scholar 

  27. P.K. Sahu, P.K. Sahu, J. Lal, D. Thavaselvam, D.D. Agarwal, Med. Chem. Res. 21, 3826 (2012)

    Article  CAS  Google Scholar 

  28. G. Felix, J. Chromatogr. A 906, 171 (2001)

    Article  CAS  Google Scholar 

  29. A. Martinez, S. Manolache, V. Gonzalez, R. Young, F. Denes, J. Biomater. Sci. Polym. E. 11, 415 (2000)

    Article  CAS  Google Scholar 

  30. F. Löscher, T. Ruckstuhl, S. Seeger, Adv. Mater. 10, 1005 (1998)

    Article  Google Scholar 

  31. B. Volkert, B. Wolf, S. Fischer, N. Li, C. Lou, Macromol. Symp. 280, 130 (2009)

    Article  CAS  Google Scholar 

  32. A. Shaabani, A. Maleki, Appl. Catal. A Gen. 331, 149 (2007)

    Article  CAS  Google Scholar 

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Acknowledgments

The Research Council of Yazd University is gratefully acknowledged for the financial support for this work.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Yazd University, Yazd, 89195-741, Islamic Republic of Iran

    Sara Azad & Bi Bi Fatameh Mirjalili

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  1. Sara Azad
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  2. Bi Bi Fatameh Mirjalili
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Correspondence to Bi Bi Fatameh Mirjalili.

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Azad, S., Mirjalili, B.B.F. Nano-TiCl2/cellulose: an eco-friendly bio-based catalyst for one-pot synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives. Res Chem Intermed 43, 1723–1734 (2017). https://doi.org/10.1007/s11164-016-2725-2

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  • DOI: https://doi.org/10.1007/s11164-016-2725-2

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