Cu(ii) immobilized on aminated epichlorohydrin activated silica (CAES): As a new, green and efficient nanocatalyst for preparation of 5-substituted-1H-tetrazoles

RSC Advances

Volumn 5, Issue 16, 2015, Pages 12372-12381

  Razavi, Nasrin ^a   Akhlaghinia, Batool ^a  

^a FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CYCLOADDITION; REUSABILITY;

CYCLOADDITION REACTION; EPICHLOROHYDRIN; MILD REACTION CONDITIONS; NANO-CATALYST; PRODUCT ISOLATION; PROTOCOL CANS; SEM-EDS; SODIUM AZIDE;

SILICA;

EID: 84922206881     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c4ra15148h     Document Type: Article

References (71)

1. (a) R. N. Butler, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, UK, 1996, vol. 4, p. 674;
2. (b) H. Singh, A. S. Chala, V. K. Kapoor, D. Paul and R. K. Malhotra, Prog. Med. Chem., 1980, 17, 151;
3. (c) V. A. Ostrovskii, M. S. Pevzner, T. P. Kofmna, M. B. Sheherbinin and I. V. Tselinskii, Targets Heterocycl. Syst., 1999, 3, 467;
4. (d) M. Hiskey, D. E. Chavez, D. L. Naud, S. F. Son, H. L. Berghout and C. A. Bome, Proc. Int. Pyrotech. Semin., 2000, 27, 3.
5. D.M. Zimmerman and R. A. Olofson, Tetrahedron Lett., 1969, 10, 5081.
6. M. Rahman, A. Roy, M. Ghosh, Sh. Mitra, A. Majee and A. Hajra, RSC Adv., 2014, 4, 6116.
7. D. R. Patil, Y. B. Wagh, P. G. Ingole, K. Singh and D. S. Dalal, New J. Chem., 2013, 37, 3261.
8. L. Bosch and J. Vilarrasa, Angew. Chem., 2007, 46, 3926.
9. G. Venkateshwarlu, A. Premalatha, K. C. Rajanna and P. K. Saiprakash, Synth. Commun., 2009, 39, 4479.
10. J. Bonnamour and C. Bolm, Chem.-Eur. J., 2009, 15, 4543.
11. D. J. Carini, J. V. Duncia, P. E. Aldrich, A. T. Chiu, A. L. Johnson, M. E. Pierce, W. A. Price, J. B. Santella and G. J. Wells, J. Med. Chem., 1991, 34, 2525.
12. Z. P. Demko and K. B. Sharpless, J. Org. Chem., 2001, 66, 7945.
13. (a) Z. P. Demko and K. B. Sharpless, Org. Lett., 2002, 4, 2525;
14. (b) F. Himo, Z. P. Demko, L. Noodleman and K. B. Sharpless, J. Am. Chem. Soc., 2002, 124, 12210;
15. (c) F. Himo, Z. P. Demko, L. Noodleman and K. B. Sharpless, J. Am. Chem. Soc., 2003, 125, 9983.
16. P. Mani, A. K. Singh and S. K. Awasthi, Tetrahedron Lett., 2014, 55, 1879.
17. (a) J. Roh, T. V. Atramonova, K. Vavrova, G. I. Koldobskii and A. Hrabalek, Synthesis, 2009, 2175;
18. (b) K. Koguro, T. Oga, S. Mitsui and R. Orita, Synthesis, 1998, 910.
19. S. K. Prajapti, A. Nagarsenkar and B. N. Babu, Tetrahedron Lett., 2014, 55, 3507.
20. D. P. Matthews, J. E. Green and A. J. Shuker, J. Comb. Chem., 2000, 2, 19.
21. A. Kumar, R. Narayanan and H. Shechter, J. Org. Chem., 1996, 61, 4462.
22. M. Nasrollahzadeh, Y. Bayat, D. Habibi and S. Moshaee, Tetrahedron Lett., 2009, 50, 4435.
23. D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo and L. Vaccaro, J. Org. Chem., 2004, 69, 2896.
24. V. S. Patil, K. P. Nandre, A. U. Borse and S. V. Bhosale, E-J. Chem., 2012, 9, 1145.
25. B. Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah and R. Narender, Synlett, 2010, 391.
26. S. J. Wittenberger and B. G. Donner, J. Org. Chem., 1993, 58, 4139.
27. (a) S. H. Watterson, Z. Xiao, D. S. Dodd, D. R. Tortolani, W. Vaccaro, D. Potin, M. Launay, D. K. Stetsko, S. Skala and P. M. Davis, J. Med. Chem., 2010, 53, 3814;
28. (b) S. Takale, S. Manave, K. Phatangare, V. Padalkar, N. Darvatkar and A. Chaskar, Synth. Commun., 2012, 42, 2375;
29. (c) Z. Du, C. Si, Y. Li, Y. Wang and J. Lu, Int. J. Mol. Sci., 2012, 13, 4696.
30. A. Khalafi-Nezhad and S. Mohammadi, RSC Adv., 2013, 3, 4362.
31. J. He, B. Li, F. Chen, Z. Xu and G. Yin, J. Mol. Catal. A: Chem., 2009, 304, 135.
32. J. Braun and W. Keller, Ber. Dtsch. Chem. Ges., 1932, 65, 1677.
33. (a) L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu and G. Yin, Chem. Commun., 2010, 46, 448;
34. (b) L. Lang, H. Zhou, M. Xue, X. Wang and Z. Xu, Mater. Lett., 2013, 106, 443.
35. M. L. Kantam, K. B. Shiva Kumar and K. Phani Raja, J. Mol. Catal. A: Chem., 2006, 247, 186.
36. M. Lakshmi Kantam, K. B. S. Kumar and C. Sridhar, Adv. Synth. Catal., 2005, 347, 1212.
37. S. M. Agawane and J. M. Nagarkar, Catal. Sci. Technol., 2012, 2, 1324.
38. G. Aridoss and K. K. Laali, Eur. J. Org. Chem., 2011, 2011, 6343.
39. M. L. Kantam, V. Balasubrahmanyam and K. B. Shiva Kumar, Synth. Commun., 2006, 36, 1809.
40. Y. S. Gyoung, J.-G. Shim and Y. Yamamoto, Tetrahedron Lett., 2000, 41, 4193.
41. T. Jin, F. Kitahara, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 2008, 49, 2824.
42. P. Mani, C. Sharma, S. Kumar and S. K. Awasthi, J. Mol. Catal. A: Chem., 2014, 392, 150.
43. D. Kong, Y. Liu, J. Zhang, H. Li, X. Wang, G. Liu, B. Li and Z. Xu, New J. Chem., 2014, 38, 3078.
44. F. Dehghani, A. R. Sardarian and M. Esmaeilpour, J. Organomet. Chem., 2013, 743, 87.
45. B. Sreedhar, A. S. Kumar and D. Yadav, Tetrahedron Lett., 2011, 52, 3565.
46. (a) D. P. Curran, S. Hadida and S. Y. Kim, Tetrahedron, 1999, 55, 8997;
47. (b) R. Shelkar, A. Singh and J. Nagarkar, Tetrahedron Lett., 2013, 54, 106.
48. B. Franca, C. Luca, M. Raimondo and S. Giovanni, J. Org. Chem., 1999, 64, 1033.
49. S. Shanmuganathana, L. Greiner and P. D. de Maríaa, Tetrahedron Lett., 2010, 51, 6670.
50. (a) M. H. Valkenberg and W. F. Holderich, Catal. Rev.: Sci. Eng., 2002, 44, 321;
51. (b) E. L. Margelefsky, R. K. Zeidan and M. E. Davis, Chem. Soc. Rev., 2008, 37, 1118;
52. (c) J. C. Hicks, R. Dabestani, A. C. Buchanan and C. W. Jones, Chem. Mater., 2006, 18, 5022;
53. (d) J. C. Hicks, R. Dabestani, A. C. Buchanan and C. W. Jones, Inorg. Chim. Acta, 2008, 361, 3024;
54. (e) M. W. McKittrick and C. W. Jones, J. Am. Chem. Soc., 2004, 126, 3052;
55. (f) K. Q. Yu, M. W. McKittrick and C. W. Jones, Organometallics, 2004, 23, 4089.
56. J. F. Fritz and J. N. King, Anal. Chem., 1976, 48, 570.
57. B. Akhlaghinia and S. Tavakoli, Synthesis, 2005, 1775.
58. B. Akhlaghinia and S. Rezazadeh, J. Braz. Chem. Soc., 2012, 23, 2197.
59. H. Sharghi, M. H. Beyzavi and M. M. Doroodmand, Eur. J. Org. Chem., 2008, 24, 4126.
60. Special Issue, V. Coman, R. Grecu, J. Wegmann, S. Bachmann and K. Albert, Stud. Univ. Babes-Bolyai, Phys., 2001, 326-331.
61. F. Adam, K. M. Hello and H. Osman, Chin. J. Chem., 2010, 28, 2383.
62. V. Aureggi and G. Sedelmeier, Angew. Chem., Int. Ed., 2007, 46, 8440.
63. S. Lossen and J. Liebigs, Ann. Chem., 1897, 298, 102.
64. V. Rama, K. Kanagaraj and K. Pitchumani, J. Org. Chem., 2011, 76, 9090.
65. A. Köennecke, R. Döme, E. Kleinpeter and E. Lippmann, Tetrahedron, 1997, 35, 1957.
66. F. Ek, L. G. Wistrand and T. Frejd, J. Org. Chem., 2003, 68, 1911.
67. Z. Yizhong, R. Yiming and C. Chun, Helv. Chim. Acta, 2009, 92, 171.
68. G. Satzinger and J. Liebigs, Ann. Chem., 1960, 638, 159.
69. A. Najafi Chermahini, A. Teimouri and A. Moaddeli, Heteroat. Chem., 2011, 22, 168.
70. A. R. Katritzky, B. E. M. El-Gendy, B. Hall, C. D. Draghici and P. J. Steel, J. Org. Chem., 2010, 75, 6468.
71. M. Herbst, J. Org. Chem., 1950, 15, 1082.