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Mesoporous silica supported samarium as recyclable heterogeneous catalyst for synthesis of 5-substituted tetrazole and 2-substituted benzothiazole

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Abstract

Synthesis of nitrogen-containing heterocycles such as tetrazoles and benzothiazoles gains immense importance as they are omnipresent structural modules often utilized in pharmaceuticals. In the present study, well ordered MCM-41 type mesoporous silica with large pore (l-MSN) was synthesized and impregnated with samarium nitrate (Sm@l-MSN). Due to high abundance of samarium relative to many catalytically active transition metals (e.g. Ru, Ir, Pt), it may offer an opportunity to develop sustainable catalysts for organic conversions. The synthesized materials were characterized using nitrogen sorption, scanning electron microscopy, energy-dispersive X-ray, elemental mapping and transmission electron microscopy. The catalytic efficiency of the materials was explored for the synthesis of tetrazoles and benzothiazoles, two very important heterocyclic moieties in medicinal chemistry and biology. The catalyst was readily recovered and recycled up to five consecutive runs without noteworthy loss of activity or leaching.

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References

  1. H. Xue, Y. Gau, B. Twamley, J.M. Shreeve, Chem. Mater. 17, 191–198 (2005)

    Article  CAS  Google Scholar 

  2. R.G. Xiong, X. Xue, H. Zhao, Angew. Chem. Int. Ed. 41, 3800–3803 (2002)

    Article  CAS  Google Scholar 

  3. Q. Ye, Y.M. Song, G.X.J. Wang, Am. Chem. Soc. 128, 6554–6555 (2006)

    Article  CAS  Google Scholar 

  4. R.N. Bulter, in Comprehensive Heterocyclic Chemistry, vol. 4, ed. by A.R.C. Katritzky, W. Rees (Pergamon, Oxford, 1996), p. 791

    Google Scholar 

  5. K.-L. Yu, R.L.J. Johnson, Org. Chem. 52, 2051–2059 (1987)

    Article  CAS  Google Scholar 

  6. J. Zabrocki, G.D. Smith, J.B. Dunbar, H. Iijima, G.R. Marshall, J. Am. Chem. Soc. 110, 5875–5880 (1988)

    Article  CAS  Google Scholar 

  7. P. Srihari, P. Dutta, R.S. Rao, J.S. Yadav, S. Chandrasekhar, P. Thombare, J. Mohapatra, A. Chatterjee, M.R. Jain, Bioorg. Med. Chem. Lett. 19, 5569–5572 (2009)

    Article  CAS  PubMed  Google Scholar 

  8. D.W. Nelson, R.J. Gregg, M.E. Kort, A. Perez-Medrano, E.A. Voight, Y. Wang, G. Grayson, M.T. Namovic, D.L. Donnelly-Roberts, W. Niforatos, P. Honore, M.F. Jarvis, C.R. Faltynek, W.A. Carroll, J. Med. Chem. 49, 3659–3666 (2006)

    Article  CAS  PubMed  Google Scholar 

  9. G. Ortar, A.S. Moriello, M.G. Cascio, L. De Petrocellis, A. Ligresti, V.D. Marzo, Bioorg. Med. Chem. Lett. 18, 2820–2824 (2008)

    Article  CAS  PubMed  Google Scholar 

  10. M. Ahmad Malik, S.A. Al-Thabaiti, M.A. Malik, Int. J. Mol. Sci. 13, 10880–10898 (2012)

    Article  CAS  Google Scholar 

  11. B.C.H. May, A.D. Abell, J. Chem. Soc. Perkin Trans. 1, 172–178 (2002)

    Google Scholar 

  12. R.C. Tuites, T.E. Whiteley, L.M. Minsk, US Patent 1,245,614 (1971)

  13. V.M. Ostrovskaya, I.A. Dyakonova, T.D. Nikolaeva, Zh. Vses. Khim. Ova. 30, 585 (1985)

    Google Scholar 

  14. M. Hiskey, D.E. Chavez, D.L. Naud, S.F. Son, H.L. Berghout, C.A. Bome, Proc. Int. Pyrotech. Semin. 27, 3–14 (2000)

    Google Scholar 

  15. Z.J. Chermahini, A.N. Chermahini, H.A. Dabbagh, B. Rezaei, N. Irannejad, Spectrochim. Acta A 178, 79–85 (2017)

    Article  CAS  Google Scholar 

  16. Z.J. Chermahini, A.N. Chermahini, H.A. Dabbagh, A. Teimouri, J. Energy Chem. 24, 770–778 (2015)

    Article  Google Scholar 

  17. G. Aromí, L.A. Barrios, O. Roubeau, P. Gamez, Coord. Chem. Rev. 255, 485–546 (2011)

    Article  CAS  Google Scholar 

  18. H.-C. Hu, X.-M. Kang, C.-S. Cao, P. Cheng, B. Zhao, Chem. Commun. 51, 10850–10853 (2015)

    Article  CAS  Google Scholar 

  19. D. Pla, D.S. Tan, D.Y. Gin, Chem. Sci. 5, 2407–2415 (2014)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. B. Maji, H. Yamamoto, Angew. Chem. Int. Ed. 53, 8714–8717 (2014)

    Article  CAS  Google Scholar 

  21. A. Hantzsch, A. Vagt, J. Liebigs Ann. Chem. 314, 339–369 (1901)

    Article  CAS  Google Scholar 

  22. D.P. Curran, S. Hadida, S.-Y. Kim, Tetrahedron 55, 8997–9006 (1999)

    Article  CAS  Google Scholar 

  23. A. Kumar, R. Narayanan, H.J. Shechter, Org. Chem. 61, 4462–4465 (1996)

    Article  CAS  Google Scholar 

  24. O.G. Mancheño, C. Bolm, Org. Lett. 9, 2951–2954 (2007)

    Article  CAS  PubMed  Google Scholar 

  25. D.S. Treitler, S. Leung, M. Lindrud, Org. Process Res. Dev. 21, 460–467 (2017)

    Article  CAS  Google Scholar 

  26. Z.P. Demko, K.B. Sharpless, J. Org. Chem. 66, 7945–7950 (2001)

    Article  CAS  PubMed  Google Scholar 

  27. Z.P. Demko, K.B. Sharpless, Org. Lett. 4, 2525–2527 (2002)

    Article  CAS  PubMed  Google Scholar 

  28. W.K. Su, Z. Hong, W.G. Shan, X.X. Zhang, Eur. J. Org. Chem. 12, 2723–2726 (2006)

    Article  CAS  Google Scholar 

  29. S. Hajra, D. Sinha, M.J. Bhowmick, Org. Chem. 72, 1852–1855 (2007)

    Article  CAS  Google Scholar 

  30. D.P. Matthews, J.E. Green, A.J. Shuker, J. Comb. Chem. 2, 19–23 (2000)

    Article  CAS  PubMed  Google Scholar 

  31. T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Chem. Asian J. 3, 1575–1580 (2008)

    Article  CAS  PubMed  Google Scholar 

  32. J. Bonnamour, C. Bolm, Chem. Eur. J. 15, 4543–4545 (2009)

    Article  CAS  PubMed  Google Scholar 

  33. D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L.J. Vaccoro, Org. Chem. 69, 2896–2898 (2004)

    Article  CAS  Google Scholar 

  34. B.S. Jursic, B.W.J. Leblanc, Heterocycl. Chem. 35, 405–408 (1998)

    Article  CAS  Google Scholar 

  35. B. Schmidt, D. Meid, D. Kieser, Tetrahedron 63, 492–496 (2007)

    Article  CAS  Google Scholar 

  36. M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50, 4435–4438 (2009)

    Article  CAS  Google Scholar 

  37. L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu, G. Yin, Chem. Commun. 46, 448–450 (2010)

    Article  CAS  Google Scholar 

  38. L. Lang, H. Zhou, M. Xue, X. Wang, Z. Xu, Mater. Lett. 106, 443–446 (2013)

    Article  CAS  Google Scholar 

  39. G. Aridoss, K.K. Laali, Eur. J. Org. Chem. 31, 6343–6355 (2011)

    Article  CAS  Google Scholar 

  40. J. He, B. Li, F. Chen, Z. Xu, G.J. Yin, Mol. Catal. A 304, 135–138 (2009)

    Article  CAS  Google Scholar 

  41. S.M. Agawane, J.M. Nagarkar, Catal. Sci. Technol. 2, 1324–1327 (2012)

    Article  CAS  Google Scholar 

  42. V. Rama, K. Kanagaraj, K.J. Pitchumani, Org. Chem. 76, 9090–9095 (2011)

    Article  CAS  Google Scholar 

  43. A. Teimouri, A.R.N. Chermahini, Polyhedron 30, 2606–2610 (2011)

    Article  CAS  Google Scholar 

  44. G.A. Meshram, S.S. Deshpande, P.A. Wagh, V.A. Vala, Tetrahedron Lett. 55, 3557–3560 (2014)

    Article  CAS  Google Scholar 

  45. P. Sivaguru, K. Bhuvaneswari, R. Ramkumar, A. Lalith, Tetrahedron Lett. 55, 5683–5686 (2014)

    Article  CAS  Google Scholar 

  46. A.N. Chermahini, M.K. Omran, H.A. Dabbagh, G. Mohammadnezhad, A. Teimouri, New J. Chem. 39, 4814–4820 (2015)

    Article  CAS  Google Scholar 

  47. B. Tahmasbi, A.G. Choghamarani, Appl. Organomet. Chem. 31, 3644 (2017)

    Article  CAS  Google Scholar 

  48. M. Nasrollahzadeh, S.M. Sajadi, Y.J. Mirzaei, Colloid Interface Sci. 468, 156–162 (2016)

    Article  CAS  Google Scholar 

  49. S.M. Sajadi, M. Maham, Lett. Org. Chem. 11, 35–39 (2014)

    Article  CAS  Google Scholar 

  50. S.M. Sajadi, M. Khalaj, S.M.H. Jamkarani, M. Mahame, M. Kashefib, Synth. Commun. 41, 3053–3059 (2011)

    Article  CAS  Google Scholar 

  51. N.P. Prajapati, R.H. Vekariya, M.A. Borad, H.D. Patel, RSC Adv. 4, 60176–60208 (2014)

    Article  CAS  Google Scholar 

  52. J.A. Asensio, P. Gomez-Romero, Fuel Cells 5, 336–343 (2005)

    Article  CAS  Google Scholar 

  53. N. Singh, D.O. Jang, Org. Lett. 9, 1991–1994 (2007)

    Article  CAS  PubMed  Google Scholar 

  54. P. Chaudhuri, B. Ganguly, S. Bhattacharya, Org. Chem. 72, 1912–1923 (2007)

    Article  CAS  Google Scholar 

  55. A. Sannigrahi, D. Arunbabu, R.M. Sankar, T. Jana, Macromolecules 40, 2844–2851 (2007)

    Article  CAS  Google Scholar 

  56. F.S. Rodembusch, T. Buckup, M. Segala, L. Tavares, R.R.B. Correia, V. Stefani, Chem. Phys. 305, 115–121 (2004)

    Article  CAS  Google Scholar 

  57. J.-R. Gong, L.-J. Wan, S.-B. Lei, C.-L. Bai, X.-H. Zhang, S.-T. Lee, J. Phys. Chem. 109, 1675–1682 (2005)

    Article  CAS  Google Scholar 

  58. Y. Li, Y.L. Wang, J.Y. Wang, Chem. Lett. 35, 460–461 (2006)

    Article  CAS  Google Scholar 

  59. A.K. Chakraborti, S. Rudrawar, K.B. Jadhav, G. Kaur, V.S. Chankeshwara, Green Chem. 9, 1335–1340 (2007)

    Article  CAS  Google Scholar 

  60. K. Bahrami, M.M. Khodaei, F. Naali, Synlett 4, 569–572 (2009)

    Article  CAS  Google Scholar 

  61. C. Mukhopadhyay, A.J. Datta, Heterocycl. Chem. 46, 91–95 (2009)

    Article  CAS  Google Scholar 

  62. B.C. Ranu, R. Jana, S.S. Dey, Chem. Lett. 33, 274–275 (2004)

    Article  CAS  Google Scholar 

  63. K. Bahrami, M.M. Khodaei, F.J. Naali, Org. Chem. 73, 6835–6837 (2008)

    Article  CAS  Google Scholar 

  64. H.-L. Xiao, J.-X. Chen, M.-C. Liu, D.-J. Zhu, J.-C. Ding, H.-Y. Wu, Chem. Lett. 38, 170–171 (2009)

    Article  CAS  Google Scholar 

  65. S. Samanta, S. Das, P. Biswas, J. Org. Chem. 78, 11184–11193 (2013)

    Article  CAS  PubMed  Google Scholar 

  66. S.S. Panda, M.A. Ibrahim, A.A. Oliferenko, A.M. Asiri, A.R. Katritzky, Green Chem. 15, 2709–2712 (2013)

    Article  CAS  Google Scholar 

  67. R. Shelkar, S. Sarode, J. Nagarkar, Tetrahedron Lett. 54, 6986–6990 (2013)

    Article  CAS  Google Scholar 

  68. S.M. Inamdar, V.K. More, S.K. Mandal, Tetrahedron Lett. 54, 579–583 (2013)

    Article  CAS  Google Scholar 

  69. P. Bandyopadhyay, M. Sathe, G.K. Prasad, P. Sharma, M.P. Kaushika, J. Mol. Catal. A 341, 77–82 (2011)

    Article  CAS  Google Scholar 

  70. S. Das, S. Samanta, S.K. Maji, P.K. Samanta, A.K. Dutta, D.N. Srivastava, B. Adhikary, P. Biswas, Tetrahedron Lett. 54, 1090–1096 (2013)

    Article  CAS  Google Scholar 

  71. P.B. Gorepatil, Y.D. Mane, V.S. Ingle, Synlett 24, 2241–2244 (2013)

    Article  CAS  Google Scholar 

  72. A.V. Narsaiah, A.R. Reddy, B.V.S. Reddy, J.S. Yadav, Synth. Commun. 40, 1750–1757 (2010)

    Article  CAS  Google Scholar 

  73. A.V. Narsaiah, A.R. Reddy, J.S. Yadav, Synth. Commun. 41, 262–267 (2011)

    Article  CAS  Google Scholar 

  74. M. Szostak, N.J. Fazakerley, D. Parmar, D.J. Procter, Chem. Rev. 114, 5959–6039 (2014)

    Article  CAS  PubMed  Google Scholar 

  75. R.V. Siriwardane, Langmuir 7, 497–502 (1991)

    Article  CAS  Google Scholar 

  76. V.T. Amorebieta, A.J. Colussi, J. Am. Chem. Soc. 118, 10236–10241 (1996)

    Article  CAS  Google Scholar 

  77. T.-D. Nguyen, D. Mrabet, T.-O. Do, J. Phys. Chem. 112, 15226–15235 (2008)

    CAS  Google Scholar 

  78. G.K. Hodgson, S. Impellizzeri, G.L. Hallett-Tapleya, J.C. Scaiano, RSC Adv. 5, 3728–3732 (2015)

    Article  CAS  Google Scholar 

  79. G.K. Hodgson, S. Impellizzeri, J.C. Scaiano, Catal. Sci. Technol. 6, 7113–7121 (2016)

    Article  CAS  Google Scholar 

  80. G.K. Hodgson, S. Impellizzeri, J.C. Scaiano, Chem. Sci. 7, 1314–1321 (2016)

    Article  CAS  PubMed  Google Scholar 

  81. I.I. Slowing, B.G. Trewyn, V.S.-Y. Lin, J. Am. Chem. Soc. 129, 8845–8849 (2007)

    Article  CAS  PubMed  Google Scholar 

  82. S.K. Das, M.K. Bhunia, A. Bhaumik, Solid State Chem. 183, 1326–1333 (2010)

    Article  CAS  Google Scholar 

  83. H.E.B. Lempers, R.A. Sheldon, J. Catal. 175, 62–69 (1998)

    Article  CAS  Google Scholar 

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Acknowledgements

PKS is indebted to UGC-India for JRF (ID-131818). P.B. acknowledges CSIR-India for the Project (Sanction letter no. 01(2459)/11/EMR-II dated 16/05/2011). MN gratefully acknowledges extramural research grant from DST-SERB (SB/FT/CS-004/2014 dated 27/06/2014), New Delhi, India.

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Samanta, P.K., Biswas, R., Das, T. et al. Mesoporous silica supported samarium as recyclable heterogeneous catalyst for synthesis of 5-substituted tetrazole and 2-substituted benzothiazole. J Porous Mater 26, 145–155 (2019). https://doi.org/10.1007/s10934-018-0626-z

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