Synthesis and characterization of new nanomagnetic particles/Tris (hydroxymethyl) aminomethan functionalized by melamine/Cu(II)nitrate and study their catalytic application in the synthesis of tetrazoles

Document Type : Original Article

Authors

1 Faculty of Science, Department of Chemistry, Arak University, Arak 38156-8-8349, Iran

2 Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran

Abstract

In this work, new nanomagnetic particles/Tris (hydroxymethyl)aminomethan functionalized with melamine/Cu(II)nitrate were synthesized and characterized. Next, the catalytic activity of these new magnetic nanoparticles was evaluated in the reaction between sodium azide and different benzontriles in the synthesis of various tetrazoles which possess importance in pharmaceuticals and agriculture. As this catalyst has shown a good catalytic activity, this procedure has led to the synthesis of these products in short reaction times and high yields. Characterization of the magnetic catalyst was carried out by different techniques namely IR, SEM, XRD, VSM, CHN and TGA. Moreover, tetrazole derivatives were characterized using IR, 1HNMR and 13CNMR spectroscopy analysis and also their melting points compared with the reported documents. This catalyst was reused for several runs without any specific loss in its catalytic activity. Finally, mild reaction conditions, no by-products and also recoverability and reusability of the catalyst made this method an environmentally friendly approach.

Graphical Abstract

Synthesis and characterization of new nanomagnetic particles/Tris (hydroxymethyl) aminomethan functionalized by melamine/Cu(II)nitrate and study their catalytic application in the synthesis of tetrazoles

Keywords

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References

1) H. Naeimi, S. Mohamadabadi, Dalton Trans. 43 (2014) 12967.
2) O. Olsvik, T. Popovic, E. Skjerve, K.S. Cudjoe, E. Hornes, J. Gelstad, M. Uhlen, Clin. Microbiol. Rev. 7 (1994) 43.
3) M.N. Widjojoatmodjo, A.C. Fluit, R. Torensma, J. Verhoef, J. Immunol. Methods. 165 (1993) 11.
4) R. Weissleder, G. Elizondo, J. Wittenberg, C.A. Rabito, H.H. Bengele, L. Josephson, Radiology 175 (1990) 489.
5) J.W.M. Bulte, L.D. Ma, R.L. Magin, R.L. Kamman, C.E. Hulstaert, K.G. Go, T.H. The, L. De Leij, Magnet. Reson. Med. 29 (1993) 32.
6) P.K. Gupta, C.T. Hung, F.C. Lam, D.G. Perrier, Int. J. Pharm. 43 (1988) 167.
7) T. Neuberger, B. Schöpf, H. Hofmann, M. Hofmann, B.V. Rechenberg, J. Magn. Mater. 293 (2005) 483.
8) A. Jordan, P. Wust, H. Fahling, Scholz, R., Int. J. Hyperthermia 9 (1993) 51.
9) U. Hafeli, W. Schutt, J. Teller, M. Zborowski, Scientific and Clinical Applications of Magnetic Carriers, Plenum Press, New York and London, 1997, pp. 527-534.
10) Z. Karimi, L. Karimi, H. Shokrollahi, Mater. Sci. Engin. C 33 (2013) 2465.
11) R.N. Butler, A.R. Katritzky, Comprehensive Heterocyclic Chemistry, C.W. Rees, E.F.V. Scriven (Ed.), Pergamon, Oxford, UK, Vol. 4, 1996.
12) M. Hiskey, D.E. Chavez, D.L. Naud, S.F. Son, H. L. Berghout, C.A. Bome, Proc. Int. Pyrotech. Semin. 27 (2000) 3.
13) M.U.S. Brown, Patent 3,338,915, 1967; Chem. Abstr., 1968, 87299.
14) V.V. Nilulin, T.V. Artamonova, G.I. Koldobskii, Russ. J. Org. Chem. 41 (2005) 444. 
15) G.I. Koldobskii, V.A. Ostrovskii, Usp. Khim. 63 (1994) 847.
16) D.M. Zimmerman, R.A. Olofson, Tetrahedron Lett. 58 (1969) 5081.
17) T. Jin, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 45 (2004) 9435.
18) Y. Satoh, N. Marcopulos, Tetrahedron Lett. 36 (1995) 1759.
19) A.K. Gupta, C.H. Song, C.H. Oh, Tetrahedron Lett. 45 (2004) 4113.
20) K. Dhiman, M. Adinath, H. Alakananda, Tetrahedron Lett. 50 (2009) 2668.
21) W. Su, Z. Hong, W. Shan, X. Zhang, Eur. J. Org. Chem. 2723 (2006).
22) D. Habibi, H. Nabavi, M. Nasrollahzadeh, J. Chem. 1 (2012).
23) T.M. Potewar, S.A. Siddiqui, R.J. Lahoti, K.V. Srinivasan, Tetrahedron Lett. 48 (2007) 1721.
24) D. Habibi, M. Nasrollahzadeh, T.A. Kamali, Green Chem. 13 (2011) 3499.
25) A. khalafi-Nezhad, S. mohammadi, RSC Adv. 3 (2013) 4362.
26) F. Dehghani, A. R. Sardarian, M. Esmaeilpour, J. Organomet. Chem. 743 (2013) 87.
27) N.T. Pokhodylo, V.S. Matiychuk, M.D. Obushak, Tetrahedron 64 (2008) 1430.
28) B. Das, Ch. R. Reddy, D.N. Kumar, M. Krishnaiah, R. Narender, Synlett 3 (2010) 391.
29) F. Himo, Z.P. Demko, L. Noodleman, K.B. Sharpless, J. Am. Chem. Soc. 124 (2002) 12210.
30) M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50 (2009) 4435.
31) Y. Zhou, Ch. Yao, R. Ni, G. Yang, Synth. Commun. 40 (2010) 2624.
32) Ch. Tao, B. Wang, L. Sun, J. Yi, D. Shi, J. Wang, W. Liu, J. Chem. Res. 41 (2016) 25.
33) A. Coca. E. Turek, Tetrahedron Lett. 55 (2014) 2718.
34) G.A. Meshram, Sh.S. Deshpande, P.A. Wagh, V.A. Vala, Tetrahedron Lett. 55 (2014) 3557.
35) V. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 76 (2011) 9090.
36) B. Sreedhar, A.S. Kumar, D. Yada, Tetrahedron Lett  52 (2011) 3565.
37) A. Coca, E. Turek, L. Feinn, Synth. Commun. 45 (2015) 218.
Iranian Journal of Chemistry
Volume 1, Issue 1 - Serial Number 1
January 2019
Pages 51-61

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History

  • Receive Date: 28 April 2018
  • Revise Date: 02 July 2018
  • Accept Date: 17 September 2018

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