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Amino-functionalized mesoporous silica as solid base catalyst for regioselective aza-Michael reaction of aryl tetrazoles

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Abstract

The modified MCM-41 with aminopropyl groups was synthesized, characterized and its catalytic activity was evaluated in aza-Michael addition of various aryl tetrazoles to activated olefin esters under reflux condition. The synthesized new compounds were characterized using spectroscopic and physical methods. The catalyst was reused in five consecutive experiments without obvious loss of activity. The results showed with application of aminopropylated MCM-41 only N2 alkylation occurs on tetrazole rings. However, when triethylamine was used as the base, a mixture of N1 and N2 alkylation was observed. In addition, antimicrobial studies investigated and results indicated that the products did not show considerable antimicrobial activity.

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References

  1. H.R. Meier, H. Heimgartner, in Methoden der Organischen Chemie (Houben-Weyl), Vol. E8d, ed by E. Schumann (Georg Thieme, Stuttgart, 1994)

  2. R.J. Herr, Bioorg. Med. Chem. 10, 3379 (2002)

    Article  CAS  Google Scholar 

  3. R.N. Butler, in Comprehensive Heterocyclic Chemistry, eds by A.R. Katritzky, C. W. Ress, E. F. V. Scriven (Pergamon, Oxford, 1996)

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

    Article  CAS  Google Scholar 

  5. M.A. Malik, Y.M. Wani, S.A. Al-Thabaiti, R.A. Shiekh, J. Incl. Phenom. Macrocycl. Chem. 78, 15 (2013)

    Article  Google Scholar 

  6. S.J. Wittenberger, Org. Prep. Proced. Int. 26, 499 (1994)

    Article  CAS  Google Scholar 

  7. G.-H. Tao, Y. Guo, Y.-H. Joo, B. Twamley, J.M. Shreeve, Mater. Chem. 18, 5524 (2008)

    Article  CAS  Google Scholar 

  8. A. Razynska, A. Tempczyk, E. Maslinski, J. Szafranek, Z. Grzonka, P. Hermann, J. Chem. Soc. Perkin Trans. 2, 379 (1983)

    Article  Google Scholar 

  9. R.N. Butler, V.C. Garvin, H. Lumbroso, C. Liegois, J. Chem. Soc. Perkin Trans. 2, 721 (1984)

    Article  Google Scholar 

  10. W.M.F. Fabian, Z. Naturforsch. 45, 1328 (1990)

    CAS  Google Scholar 

  11. M.W. Wong, R. Leung-Toung, C. Wentrup, J. Am. Chem. Soc. 115, 2465 (1993)

    Article  CAS  Google Scholar 

  12. A.P. Mazurek, N. Sadlej-Sosnowska, Chem. Phys. Lett. 330, 212 (2000)

    Article  CAS  Google Scholar 

  13. N. Sadlej-Sosnowska, J. Org. Chem. 66, 8737 (2001)

    Article  CAS  Google Scholar 

  14. A.N. Chermahini, M. Nasr-Esfahani, Z. Dalirnasab, A.H. Dabbagh, A. Teimouri, J. Mol. Struct. Theochem 820, 7 (2007)

    Article  Google Scholar 

  15. G.I. Koldobskii, R.B. Kharbash, Russ. J. Org. Chem. 39, 453 (2003)

    Article  CAS  Google Scholar 

  16. J. Roh, K. Vávrová, A. Hrabálek, Eur. J. Org. Chem. 2011, 6101 (2012)

    Article  Google Scholar 

  17. B.V. Rokade, K. Gadde, K.R. Prabhu, Adv. Synth. Catal. 356, 946 (2014)

    Article  CAS  Google Scholar 

  18. G. Aridoss, K.K. Laali, Eur. J. Org. Chem. 2012, 6343 (2011)

    Article  Google Scholar 

  19. S. Kumar, A. Kumar, A. Agarwal, S.K. Awasthi, RSC Adv. 5, 21651 (2014)

    Article  Google Scholar 

  20. G.M. Schroeder, S. Marshall, H. Wan, A.V. Purandare, Tetrahedron Lett. 51, 1404 (2010)

    Article  CAS  Google Scholar 

  21. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature 359, 710 (1992)

    Article  CAS  Google Scholar 

  22. A.L. de Lima, A. Mbengue, R.A.S. San Gil, C.M. Ronconi, C.A. Mota, Catal. Today 226, 210 (2014)

    Article  Google Scholar 

  23. R. Bal, K. Chaudhari, S. Sivasanker, Catal. Lett. 75, 75 (2000)

    Article  Google Scholar 

  24. M.J. Climent, A. Corma, S. Iborra, L. Marti, ChemSusChem 7, 1177 (2014)

    Article  CAS  Google Scholar 

  25. Q. Yang, M.P. Kapoor, N. Shirokura, M. Ohashi, S. Inagaki, J.N. Kondo, K. Domen, J. Mater. Chem. 15, 666 (2005)

    Article  CAS  Google Scholar 

  26. R.V. Crieken, J.A. Melero, G. Morales, J. Mol. Catal. A 256, 29 (2006)

    Article  Google Scholar 

  27. J.A. Posada, C.A. Cardona, O. Giraldo, Mater. Chem. Phys. 121, 215 (2010)

    Article  CAS  Google Scholar 

  28. G.Q. Silveira, M.D. Vargas, C.M. Ronconi, J. Mater. Chem. 21, 6034 (2011)

    Article  CAS  Google Scholar 

  29. X. Wang, S. Cheng, Catal. Commun. 7, 689 (2006)

    Article  CAS  Google Scholar 

  30. D. Macquarrie, D. Jackson, Chem. Commun. 1781 (1997)

  31. N. Shadjou, M. Hasanzadeh, RSC Adv. 4, 18117 (2014)

    Article  CAS  Google Scholar 

  32. G. Sartori, F. Bigi, R. Maggi, R. Sartorio, D. Macquarrie, M. Lenarda, L. Storaro, S. Coluccia, G. Martra, J. Catal. 222, 410 (2004)

    Article  CAS  Google Scholar 

  33. M. Sánchez-Roselló, J.L. Aceña, A. Simón-Fuentesa, C. del Pozo, Chem. Soc. Rev. 43, 7430 (2014)

    Article  Google Scholar 

  34. M. Sánchez-Roselló, C. Mulet, M. Guerola, C. del Pozo, S. Fustero, Chem. Eur. J. 20, 15697 (2014)

    Article  Google Scholar 

  35. P. Chauhan, D. Enders, Angew. Chem. Int. Ed. 53, 1485 (2014)

    Article  CAS  Google Scholar 

  36. J. Cheng, Z. Huang, Y.R. Chi, Angew. Chem. Int. Ed. 52, 8592 (2013)

    Article  CAS  Google Scholar 

  37. B.M. Reddy, M.K. Patil, B.T. Reddy, Catal. Lett. 126, 413 (2008)

    Article  CAS  Google Scholar 

  38. S. Boncel, K. Saletra, B. Hefczyc, K.Z. Walczak, Beilstein J. Org. Chem. 7, 173 (2011)

    Article  CAS  Google Scholar 

  39. U. Uria, J.L. Vicario, D. Badía, L. Carrillo, Chem. Commun. 2509 (2007)

  40. J.M. Xu, C. Qian, B.K. Liu, Q. Wu, X.F. Lin, Tetrahedron 63, 986 (2007)

    Article  CAS  Google Scholar 

  41. L. Yang, L.W. Xu, C.G. Xia, Tetrahedron Lett. 46, 3279 (2005)

    Article  CAS  Google Scholar 

  42. G. Bartoli, M. Bartolacci, A. Giuliani, E. Marcantoni, M. Massaccesi, E. Torregiani, J. Org. Chem. 70, 169 (2005)

    Article  CAS  Google Scholar 

  43. J. Lv, H. Wu, Y. Wang, Eur. J. Org. Chem. 11, 2073 (2010)

    Article  Google Scholar 

  44. M. Gandelman, E.N. Jacobsen, Angew. Chem. Int. Ed. 44, 2393 (2005)

    Article  CAS  Google Scholar 

  45. F. Han, L. Yang, Z. Li, C. Xia, Org. Biomol. Chem. 10, 346 (2012)

    Article  CAS  Google Scholar 

  46. H. Dziklinska, S. Dzierzgowski, A. Jezewski, J. Plenkiewicz, Bull. Soc. Chim. Belg. 98, 277 (1989)

    Article  CAS  Google Scholar 

  47. A. Alami, A. El Hallaoui, A. Elachqar, S. El Hajji, M.L. Roumestant, Ph Viallefont, Prep. Biochem. Biotechnol. 28, 167 (1998)

    Article  CAS  Google Scholar 

  48. A.N. Chermahini, A. Teimouri, F. Momenbeik, A. Zarei, Z. Dalirnasab, A. Ghaedi, M. Roosta, J. Heterocycl. Chem. 47, 913 (2010)

    Article  CAS  Google Scholar 

  49. A.N. Chermahini, A. Teimouri, A. Moadeli, Heteroatom Chem. 22, 168 (2011)

    Article  CAS  Google Scholar 

  50. A. Teimouri, A.N. Chermahini, Polyhedron 30, 2606 (2011)

    Article  CAS  Google Scholar 

  51. D. Kumar, K. Schumacher, C. du Fresne von Hohenesche, M. Grun, K.K. Unger, Coll. Surf. A Physicochem. Eng. Aspects 187–188, 109 (2001)

    Article  Google Scholar 

  52. G. Romanelli, G. Pasquale, Á. Sathicqa, H. Thomas, J. Autino, P. Vázquez, J. Mol. Cat. A 340, 24 (2011)

    Article  CAS  Google Scholar 

  53. V. Antochshuk, M. Jaroniec, Chem. Commun. 3, 258 (2002)

    Article  Google Scholar 

  54. L.T. Gibson, Chem. Soc. Rev. 43, 5163 (2014)

    Article  CAS  Google Scholar 

  55. G.I. Koldobskii, V.A. Ostrovskii, Russ. Chem. Rev. 63, 797 (1981)

    Article  Google Scholar 

  56. H. Singh, A.S. Chawla, V.K. Kapoor, D. Paul, R.K. Malhorta in Progress in Medicinal Chemistry, vol 17, eds by G.P. Ellis, G.B. (West 1980), p. 151

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Acknowledgments

This work was financially supported by the Ms.C. Programs Foundation of Yasouj University and Isfahan University of Technology.

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Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84154-83111, Iran

    Alireza Najafi Chermahini & Mahboobeh Azadi

  2. Department of Chemistry, Faculty of Science, Yasouj University, Yasouj, Iran

    Elham Tafakori

  3. Chemistry Department, Payame Noor University (PNU), Tehran, 19395-4697, Iran

    Abbas Teimouri

  4. Department of Agronomy and Plant Breeding, College of Agriculture, Isfahan University of Technology, Isfahan, 84156-83111, Iran

    Mohammadreza Sabzalian

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  1. Alireza Najafi Chermahini
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Correspondence to Alireza Najafi Chermahini.

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Najafi Chermahini, A., Azadi, M., Tafakori, E. et al. Amino-functionalized mesoporous silica as solid base catalyst for regioselective aza-Michael reaction of aryl tetrazoles. J Porous Mater 23, 441–451 (2016). https://doi.org/10.1007/s10934-015-0098-3

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