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Cu-MCM-41 nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition reaction of nitriles and sodium azide

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Abstract

[3 + 2] cycloaddition reaction of various types of nitriles and sodium azide (NaN 3) were studied in the presence of nano-sized Cu-MCM-41 as an efficient recoverable heterogeneous catalyst. Nano-sized Cu-MCM-41 mesoporous molecular sieves with various Si/Cu molar ratios were synthesized by direct insertion of metal ions at room temperature. The textural properties of the materials have been studied by means of XRD, FTIR, SEM and TEM techniques. Catalytic behavior of Cu-MCM-41 was also investigated by pyridine absorption and potentiometric titration. The reactions data verified characterization results and show that Cu-MCM-41 with Si/Cu molar ratio of 20 has considerably better catalytic activity compared to the other molar ratios. To investigate reusability, the catalyst was recovered by simple filtration and reused for several cycles with consistent activity.

Nano-sized Cu-MCM-41 mesoporous molecular sieves with various Si/Cu molar ratios were synthesized by direct insertion of metal ions at room temperature. [3+2] cycloaddition reaction of various types of nitriles and sodium azide (NaN3) were studied in the presence of nano-sized Cu-MCM-41 as an efficient recoverable heterogeneous catalyst.

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References

  1. Holland G F and Pereira J N 1967 J. Med. Chem. 10 149

    Article  CAS  Google Scholar 

  2. Xue H, Gao Y, Twamley B and Shreeve J n M 2004 Chem. Mater. 17 191

    Article  Google Scholar 

  3. Herr R J 2002 Biorg. Med. Chem. 10 3379

    Article  CAS  Google Scholar 

  4. Gutmann B, Roduit J P, Roberge D and Kappe C O 2010 Angew. Chem. Int. Ed. Engl. 49 7101

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  6. Patil D, Deshmukh M and Dalal D 2012 J. Iranian Chem. Soc. 9 799

    Article  CAS  Google Scholar 

  7. Amantini D, Beleggia R, Fringuelli F, Pizzo F and Vaccaro L 2004 J. Org. Chem. 69 2896

    Article  CAS  Google Scholar 

  8. Herbst R M and Wilson K R 1957 J. Org. Chem. 22 1142

    Article  CAS  Google Scholar 

  9. Kumar A, Narayanan R and Shechter H 1996 J. Org. Chem. 61 4462

    Article  CAS  Google Scholar 

  10. Matthews D P, Green J E and Shuker A J 1999 J. Comb. Chem. 2 19

    Article  Google Scholar 

  11. Jin T, Kitahara F, Kamijo S and Yamamoto Y 2008 Tetrahedron Lett. 49 2824

    Article  CAS  Google Scholar 

  12. Lakshmi Kantam M, Kumar K B S and Sridhar C 2005 Adv. Synth. Catal. 347 1212

    Article  Google Scholar 

  13. Chermahini A N, Teimouri A and Moaddeli A 2011 Heteroat. Chem. 22 168

    Article  CAS  Google Scholar 

  14. Abdollahi-Alibeik M and Pouriayevali M 2012 Catal. Commun. 22 13

    Article  CAS  Google Scholar 

  15. Sivaguru P, Parameswaran K, Kiruthiga M, Vadivel P and Lalitha A 2014 J. Iranian. Chem. Soc. 12 95

  16. Farzaneh F, Zamanifar E and Williams C D 2004 J. Mol. Catal. A: Chem. 218 203

    Article  CAS  Google Scholar 

  17. Choi J -S, Yoon S -S, Jang S -H and Ahn W -S 2006 Catal. Today 111 280

    Article  CAS  Google Scholar 

  18. Wang L, Kong A, Chen B, Ding H, Shan Y and He M 2005 J. Mol. Catal. A: Chem. 230 143

    Article  CAS  Google Scholar 

  19. Vetrivel S and Pandurangan A 2006 J. Mol. Catal. A: Chem. 246 223

    Article  CAS  Google Scholar 

  20. Cortés Corberán V, Jia M J, El-Haskouri J, Valenzuela R X, Beltrán-Porter D and Amorós P 2004 Catal. Today 91–92 127

    Article  Google Scholar 

  21. Szegedi A, Popova M, Mavrodinova V, UrbaÌ n M, Kiricsi I and Minchev C 2007 Microporous Mesoporous Mater. 99 149

    Article  CAS  Google Scholar 

  22. Higashimoto S, Hu Y, Tsumura R, Iino K, Matsuoka M, Yamashita H, Shul Y G, Che M and Anpo M 2005 J. Catal. 235 272

    Article  CAS  Google Scholar 

  23. Sreedhar B, Kumar A S and Yada D 2011 Tetrahedron Lett. 52 3565

    Article  CAS  Google Scholar 

  24. Sobczak I, Ziolek M, Renn M, Decyk P, Nowak I, Daturi M and Lavalley J -C 2004 Microporous Mesoporous Mater. 74 23

    Article  CAS  Google Scholar 

  25. Liu C -C and Teng H 2005 Appl. Catal. B 58 69

    Article  CAS  Google Scholar 

  26. Abdollahi-Alibeik M and Rezaeipoor-Anari A 2014 Cat. Sci. Tech. 4 1151

    Article  CAS  Google Scholar 

  27. Pizzio L R, Vázquez P G, Cáceres C V and Blanco M N 2003 Appl. Catal. A 256 125

    Article  CAS  Google Scholar 

  28. Demko Z P and Sharpless K B 2001 J. Org. Chem. 66 7945

    Article  CAS  Google Scholar 

  29. Cantillo D, Gutmann B and Kappe C O 2012 J. Org. Chem. 77 10882

    Article  CAS  Google Scholar 

  30. Jursic B S and Leblanc B W 1998 J. Heterocycl. Chem. 35 405

    Article  CAS  Google Scholar 

  31. Elpern B and Nachod F C 1950 J. Am. Chem. Soc. 72 3379

    Article  CAS  Google Scholar 

  32. Shelkar R, Singh A and Nagarkar J 2013 Tetrahedron Lett. 54 106

    Article  CAS  Google Scholar 

  33. Rama V, Kanagaraj K and Pitchumani K 2011 J. Org. Chem. 76 9090

    Article  CAS  Google Scholar 

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ABDOLLAHI-ALIBEIK, M., MOADDELI, A. Cu-MCM-41 nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition reaction of nitriles and sodium azide. J Chem Sci 128, 93–99 (2016). https://doi.org/10.1007/s12039-015-1005-9

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