Web of Science (Emerging Sources Citation Index)

Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran.

2 Department of Organic Chemistry, Faculty of Chemistry, Bu‐Ali Sina University, 6517838683 Hamedan, Iran

3 Medicinal Plants and Natural Products Research Center, Hamadan University of Medical Sciences, Hamadan, Iran

10.33945/SAMI/ECC.2020.7.8

Abstract

Boron sulfuric acid (BSA) is an efficient heterogeneous catalyst for the synthesis of 1-substituted 1H-1, 2, 3, 4-tetrazoles from the reaction of aryl and alkyl amines with triethyl orthoformate and sodium azide at 120 oC in polyethylenglicole (PEG).

Graphical Abstract

Keywords

Main Subjects

[1] J. Zhu and H. Bienayme, (Eds) Multicomponent Reactions; Wiley-VCH: Weinheim Germany, 2005, ISBN 3527604243.

[2] A. Domling, Chem. Rev., 2006, 106, 17-89.

[3] A. Burger, Prog. Drug Res., 1991, 37, 287-371.

[4] H. Singh, A.S. Chawla, V.K. Kapoor, D. Paul and R.K. Malhotra, Prog. Med. Chem., 1980,17, 151-183.

[5] M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.S. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert and B.H. Yagi, J.Med. Chem., 2000, 43, 953-970.

[6] P. Ward, D.R. Armour, D.E. Bays, B. Evans, G.M.P. Giblin, N. Hernon, T. Hubbard, K. Liang, D. Middlemiss, J. Mordaunt, A. Naylor, N.A. Pegg, M.V. Vinader, S.P. Watson, C. Bountra, and D.C. Evans, J. Med. Chem., 1995, 38, 4985-4992.

[7] R.J. Herr, Bioorg. Med. Chem., 2002, 10, 3379-3393.

[8] R.N. Bulter, C.W. Ress, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry, vol. 4, Pergamon, Oxford, UK, 1996, pp. 621.

[9] A.R. Katritzky and C.W. Ress, Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1984.

[10] A.R. Katritzky, C.W. Ress and E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II, Pergamon Press, Oxford, 1996.

[11] B.S. Jursic, and B.W. LeBlanc, J. Heterocycl. Chem., 1998, 35, 405-408.

[12] (a) V.A. Ostrovskii, G.I. Koldobskii, R.E. Trifonov, Tetrazoles. In: Comprehensive heterocyclic chemistry III.; (b) A.R. Katrizky, C.A. Ramsden, E.F.V. Scriven, Taylor R.J.K, Eds.; Elsevier: Oxford, 2008, Vol.6, pp.257-424.

[13] E.O. John, R.L. Kirchmeier, J.M. Shreeve, Inorg. Chem., 1989, 28, 4629-4633.

[14] C.Z. Xu, X. Heming, Int. J. Quantum Chem., 2000, 79, 350-357.

[15] G. Steinhauser, T.M. Klapotke, Angew. Chem. Int. Ed., 2008, 47, 3330-3347.

[16] F.R. Benson, Chem. Rev., 1947, 47, 1-61.

[17] G.I. Koldobskii, V.A. Ostrovskii, V.S. Popavskii, Chem. Heterocycl. Comp., 1982, 17,965-988.

[18] P.K. Kadaba, Synthesis, 1973,71-84.          

[19] A.R. Katritzky, B.V. Rogovoy, K.V. Kovalenko, J. Org. Chem., 2003, 68, 4941-4943.

[20] D.M. Zimmerman, R.A. Olofson, Tetrahedron Lett., 1969, 58, 5081-5084.

[21] F.G. Fallon, R.M. Herbst, J. Org. Chem., 1957, 22, 933-936.

[22] T. Jin, S. Kamijo, Y. Yamamoto, Tetrahedron Lett., 2004, 45, 9435-9437.

[23] Y. Satoh, N. Marcopulos, Tetrahedron Lett., 1995, 36, 1759-1762.

[24] A.K. Gupta, C.H. Oh, Tetrahedron Lett., 2004, 45, 4113-4116.

[25] W. Su, Z. Hong, W. Shan, X. Zhang, Eur. J. Org. Chem., 2006, 2006, 2723-2726: https://doi.org/10.1002/ejoc.200600007

[26] G. Thirunarayanan, G. Vanangamudi, Arkivoc, 2006, xii, 58-64.

[27] D.M. Pore, U.V. Desai, T.S. Thopate, P.P. Wadgaonkar, Arkivoc, 2006, xii, 75-80.

[28] H. Wu, Y. Shen, L. Fan, Y. Wan, D. Shi, Tetrahedron, 2006, 62, 7995-7998.

[29] J.D. Moore, R.H.  Herpel, J.R. Lichtsinn, D.L. Flynn, P.R. Hanson, Org. Lett., 2003, 5, 105-107.

[30] S. Sajjadifar, O. Louie, J. Chem. (2013) ID 674946, 6 pages (http://dx.doi.org/10.1155/2013/674946).

[31] S. Sajjadifar, Int. J. ChemTech Res., 2013,5, 385-389(2013).

[32] S. Sajjadifar, Am. J. Org. Chem., 2012, 2, 116-121.

[33] M.A. Zolfigol, H. Vahedi, A. Massoudi, S. Sajjadifar, O. Louie, N. Javaherneshan, Clin. Biochem., 2011, 44, S219.

[34] (a) S. Sajjadifar, M.A. Zolfigol, G. Chehardoli, S. Miri, P. Moosavi, Int. J. ChemTech Res., 2013, 5, 422-429; (b) A. Khazaei, M.A. Zolfigol, T. Faal-Rastegar, G. Chehardoli, S. Mallakpour, Iran. J. Catal., 2013, 3, 211-220.

[35] (a) A. Khazaei, M.A. Zolfigol, M. Mokhlesi, F. Derakhshan Panah, S. Sajjadifar, Helv.Chim. Acta, 2012, 95, 106-114(2012); (b) G. Chehardoli, M.A. Zolfigol, S.B. Azimi, E. Alizadeh, Chin. Chem. Lett., 2011,22, 827-830.

[36] (a) S. Sajjadifar, S.A. Mirshokraie, N. Javaherneshan, O. Louie, Am. J. Org. Chem., 2012,2, 1-6; (b) S. Sajjadifar, S. Mohammadi-Aghdam, Asian J. Green. Chem., 2017, 1, 1-15; (c) S. Sajjadifar, V. Azizkhani, K. Pal, H. Jabbari, O. Pouralimardan, F. Divsar, S. Mohammadi-Aghdam, I. Amini, H. Hamidi, Chem. Methodol., 2019, 3, 226-236.

[37] H. Veisi, A. Sedrpoushan, P. Mohammadi, A.R. Faraji, S. Sajjadifar, RSC Adv., 2014,4, 25898-25903.

[38] (a) H. Veisi, D. Kordestani, S. Sajjadifar, M. Hamelian, Iran. Chem. Commun., 2014, 2, 27-33; (b) S. Sajjadifar, H. Hamidi, K. Pal, J. Chem. Rev., 2019, 1, 35-46; (c) S. Sajjadifar, I. Amini, H. Jabbari, O. Pouralimardan, M.H. Fekri, K. Pal, Eurasian Chem. Commun., 2019, 1, 191-199; (d) S. Sajjadifar, I. Amini, G. Mansouri, S. Alimohammadi, Eurasian Chem. Commun., 2020, 2, 626-633.

[39] T.M. Potewar, S.A. Siddiqui, R.J. Lahoti, K.V. Srinivasan, Tetrahedron Lett., 2007, 48, 1721-1724.

[40] J. Gaire, J. McGinley, A. Fleming, F. Kelleher, Tetrahedron, 2012, 68, 5935-5941.