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

محورهای موضوعی : Iranian Journal of Catalysis

Hossein Naeimi ¹ , Fatemeh Kiani ² , Mohsen Moradian ³

1 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R. Iran.
2 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R. Iran.
3 - Institute of Nanoscience and Nanotechnology, University of Kashan, Kashan, P.O. Box: 87317-51167, I.R. Iran.

تاریخ دریافت : 1392/06/20 تاریخ پذیرش : 1392/09/25 تاریخ انتشار : 1392/09/10

کلید واژه: Solvent-free, Methanesulfonic acid, Room temperature, 1H-tetrazoles, Primary amines,

چکیده مقاله :

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.

منابع و مأخذ:

[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.