Facile and mild synthesis of 1-substituted-1H-1,2,3,4-tetrazoles catalyzed by methanesulfonic acid under solvent-free conditions

Iranian Journal of Catalysis

مقاله 8، دوره 3، شماره 4، اسفند 2013، صفحه 243-247   

نویسندگان

Hossein Naeimi^{* 1}؛ Fatemeh Kiani¹؛ Mohsen Moradian²

¹Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R. Iran.

²Institute of Nanoscience and Nanotechnology, University of Kashan, Kashan, P.O. Box: 87317-51167, I.R. Iran.

چکیده

Methanesulfonic acid (MSA) was found to be an efficient catalyst for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles. A series of 1-substituted tetrazole compounds were synthesized from the reaction of various primary amines, sodium azide and triethyl orthoformate in the presence of catalytic amounts of MSA at room temperature. In this protocol, some of the tetrazole derivatives were synthesized in good to excellent yields and convenient reaction times. This method has the advantages of simple methodology and easy work-up.

کلیدواژه‌ها

1H-tetrazoles؛ Methanesulfonic acid؛ Solvent-free؛ Room temperature؛ Primary amines

مراجع

[1] R.N. Butler, in: R.K. Alan, W.R. Charles, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry II, Pergamon, Oxford, 1996, pp. 621-678.
[2] A. Burger, Prog. Drug. Res., 37 (1991) 287-371.
[3] W.K. Su, Z. Hong, W.G. Shan, X.X. Zhang, Eur. J. Org. Chem., 2006 (2006) 2723-2726.
[4] H. Singh, A.S. Chawla, V.K. Kapoor, D. Paul, R.K. Malhotra, Prog. Med. Chem., 17 (1980) 151-183.
[5] E. Muraglia, O.D. Kinzel, R. Laufer, M.D. Miller, G. Moyer, V. Munshi, F. Orvieto, M.C. Palumbi, G. Pescatore, M. Rowley, Bioorg. Med. Chem. Lett., 16 (2006) 2748-2752.
[6] L.J. Goossen, B. Melzer, J. Org. Chem., 72 (2007) 7473-7476.
[7] C. Zhang, G. Zheng, L. Fang, Y. Li, Synlett, 17 (2006) 475-477.
[8] E.A. Popova, R.E. Trifonov, V.A. Ostrovskii, Arkivoc., 1 (2012) 45-65.
[9] A.K. Gupta, C.H. Song, C.H. Oh, Tetrahedron lett., 45 (2004) 4113-4116.
[10] L.G. Qiao, A. Asif, W.F. Shi, Sci. China: Chem., 54 (2011) 1461-1467.
[11] M.H.V. Huynh, M.A. Hiskey, D.E. Chavez, D.L. Naud, R.D. Gilardi, J. Am. Chem. Soc., 127 (2005) 12537-12543.
[12] E. Oliveri-Mandala, B. Alagna, Gazz. Chim. Ital., 40 (1910) 441-448.
[13] F.G. Fallon, R.M. Herbst, J. Org. Chem., 22 (1957) 933-936
[14] Y. Satoh, N. Marcopulos, Tetrahedron lett., 36 (1995) 1759-1762.
[15] T.M. Potewar, S.A. Siddiqui, R.J. Lahoti, K.V. Srinivasan, Tetrahedron lett., 48 (2007) 1721-1724.
[16] D. Habibi, M. Nasrollahzadeh, A.T. Kamali, Green Chem., 13 (2011) 3499-3504.
[17] D. Habibi, H. Nabavi, M. Nasrollahzadeh, J. Chem., 2013 (2013) 1-4.
[18] D. Kundu, A. Majee, A. Hajra, Tetrahedron Lett., 50 (2009) 2668-2670.
[19] S.N. Dighe, K.S. Jain, K.V. Srinivasan, Tetrahedron Lett., 50 (2009) 6139-6142.
[20] K. Kuffner, W. Lassig, E. Meier, E. Ranz, K.W. Schranz, in: U.S. Patent (Ed.), United States Patent, Agfa-Gevaert Aktiengesellschaft (DE), USA, 1978.