Montmorillonite KSF as a very efficient heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles
الموضوعات : Iranian Journal of CatalysisRahman Hosseinzadeh 1 , Zahra Lasemi 2 , Farzaneh Maliji 3
1 - Department of Organic Chemistry, Factually of Chemistry, University of Mazandaran, Babolsar, Iran.
2 - Department of Chemistry, Firoozkooh branch, Islamic Azad University, Firoozkooh, Iran.
3 - Department of Organic Chemistry, Factually of Chemistry, University of Mazandaran, Babolsar, Iran.
الکلمات المفتاحية: Heterogeneous catalyst, Sodium azide, Nitriles, [3+2] Cycloaddition, Tetrazoles, Montmorillonite KSF,
ملخص المقالة :
Montmorillonite KSF has been used as an effective and non-toxic heterogeneous catalyst for one-pot synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition of sodium azide with a wide variety of nitriles. The reaction afforded high yields of the desired products in a short reaction time under mild reaction conditions. The catalyst can be recovered by simple filtration and reused for more consecutive trials without a significant decrease in activity. To avoid using toxic catalyst and catalyst recycling make this synthesis a truly green procedure.
[1] R.J. Herr, Bioorg. Med. Chem. 10 (2002) 3379-3393.
[2] R.P. Singh, R.D. Verma, D.T. Meshri, J.M. Shreeve, Angew. Chem. Int. Ed. 45 (2006) 3584-3601.
[3] T. Okabayashi, H. Kano, Y. Makisumi, Chem. Pharm. Bull. 8 (1960) 157-162.
[4] R.S. Upadhayaya, S. Jain, N. Sinha, N. Kishore, R. Chandra, S.K. Arora, Eur. J. Med. Chem. 39 (2004) 579-592.
[5] J.T. Witkowski, R.K. Robins, R.W. Sidwell, L.N. Simon, J. Med. Chem. 15 (1972) 1150-1154.
[6] J.R. Maxwell, D.A. Wasdahl, A.C. Wolfson, V.I. Stenberg, J. Med. Chem. 27 (1984) 1565-1570.
[7] P.F. Juby, T.W. Hudyma, M. Brown, J. Med. Chem. 11 (1968) 111-117.
[8] S. Hayao, H.J. Havera, W.G. Strycker, T.J. Leipzig, R. Rodriguez, J. Med. Chem. 10 (1967) 400-402.
[9] S.K. Figdor, M.S. Von Wittenau, J. Med. Chem. 10 (1967) 1158-1159.
[10] L.M.T. Frija, R. Fausto, R.M.S. Loureiro, M.L.S. Cristiano, J. Mol. Catal. A: Chem. 305 (2009) 142-146.
[11] P.K. Kadaba, Synthesis (1973) 71-84.
[12] S.J. Wittenberger, Org Prep. Proc. Int. 26 (1994) 499-531.
[13] D. Habibi, M. Nasrollahzadeh, A.R. Faraji, Y. Bayat, Tetrahedron 66 (2010) 3866-3870.
[14] M. Nasrollahzadeh, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50 (2009) 4435-4438.
[15] D.P. Matthews, J.E. Green, A.J. Shuker, J. Comb. Chem. 2 (2000) 19-23.
[16] A. Kumar, R. Narayanan, H. Shechter, J. Org. Chem. 61 (1996) 4462-4465.
[17] D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccoro, J. Org. Chem. 69 (2004) 2896-2898.
[18] Y.S. Gyoung, J.G. Shim, Y. Yamamoto, Tetrahedron Lett. 41 (2000) 4193-4196.
[19] M.L. Kantam, K.B. Shiva Kumar, K. Phani Raja, J. Mol. Catal. A: Chem. 247 (2006) 186-188.
[20] M. Lakshmi Kantam, K.B. Shiva Kumar, C. Sridhar, Adv. Synth. Catal. 347 (2005) 1212-1214.
[21] A. Najafi Chermahini, A. Teimouri, F. Momenbeik, A. Zarei, Z. Dalirnasab, A. Ghaedi, M.J. Roosta, Heterocyclic Chem. 47 (2010) 913-922.
[22] O. Marvi, A. Alizadeh, S. Zarrabi, Bull. Korean Chem. Soc. 32 (2011) 4001-4004.
[23] A. Najafi Chermahini, A. Teimouri, A. Moaddeli, Heteroatom Chem. 22 (2011) 168-173.
[24] V. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 76 (2011) 9090-9095.
[25] B. Akhlaghinia, S. Rezazadeh, J. Braz. Chem. Soc. 23 (2012) 2197-2203.
[26] G. Venkateshwarlu, A. Premalatha, K.C. Rajanna, P.K. Saiprakash, Synth. Commun. 39 (2009) 4479-4485.
[27] G. Venkateshwarlu, K.C. Rajanna, P.K. Saiprakash, Synth. Commun. 39 (2009) 426-432.
[28] M.R. Bhosle, D.S. Shaikh, L.D. Khillare, A.R. Deshmukh, R.A. Mane, Synth. Commun. 47 (2017). 695-703.
[29] K. Ishihara, M. Kawashima, T. Shioiri, M. Matsugi, Synlett 27 (2016) 2225-2228.
[30] F. Abrishami, M. Ebrahimikia, F. Rafiee, Iran. J. Catal. 6 (2016) 245-251.
[31] N. Nowrouzi, S. Farahi, M. Irajzadeh, Lett. Org. Chem. 13 (2016) 113-119.
[32] S. Khaghaninejad, M.M. Heravi, T. Hosseinnejad, H.A. Oskooie, M. Bakavoli, Res. Chem. Intermed. 42 (2016) 1593-1610.
[33] Z. Du, Ch. Si, Y. Li, Y. Wang, J. Lu, Int. J. Mol. Sci. 13 (2012) 4696-4703.
[34] Y. Zhu, Y. Ren, Ch. Cai, Helv. Chim. Acta 92 (2009) 171-175.
[35] T. Jin, F. Kitahara, Sh. Kamijo, Y. Yamamoto, Tetrahedron Lett. 49 (2008) 2824-2827.
[36] Z.P. Demko, K.B. Sharpless, J. Org. Chem. 66 (2001) 7945-7950.
[37] M. Lakshmi Kantam, V. Balasubrahmanyam, K.B. Shiva Kumar, Synth. Commun. 36 (2006) 1809-1814.
[38] F. Himo, Z.P. Demko, L. Noodleman, K.B. Sharpless, J. Am. Chem. Soc. 124 (2002) 12210-12216.
[39] S. Takale, S. Manave, K. Phatangare, V. Padalkar, N. Darvatkar, A. Chaskar, Synth. Commun. 42 (2012) 2375-2381.
[40] Y. Zhou, Ch. Yao, R. Ni, G. Yang, Synth. Commun. 40 (2010) 2624-2632.
[41] B. Sreedhar, A. Suresh Kumar, D. Yada, Tetrahedron Lett. 52 (2011) 3565-3569.
[42] S.M. Sajadi, M. Naderi, Sh. Babadoust, J. Nat. Sci. Res. 1 (2011) 10-17.
[43] S.M. Sajadi, M. Khalaj, S.M. Hosseini Jamkarani, M. Mahame, M. Kashefib, Synth. Commun. 41 (2011) 3053-3059.
[44] A. Teimouri, A. Najafi Chermahini, Polyhedron 30 (2011) 2606-2610.
[45] L. Lang, B. Li, W. Liu, L. Jiang, Z. Xu, G. Yin, Chem. Commun. 46 (2010) 448-450.
