Acacia concinna pod catalyzed synthesis of 2-arylbenzothia/(oxa)zole derivatives
الموضوعات : Iranian Journal of Catalysis
Rahul Bhat
1
(Department of Chemistry, Rajaram College, Kolhapur 416004, India.)
Shrikrishna Karhale
2
(Department of Chemistry, Rajaram College, Kolhapur 416004, India.)
Satyanarayan Arde
3
(Department of Chemistry, Y. C. Warana Mahavidyalaya, Warananagar, Kolhapur.416113, India.)
Vasant Helavi
4
(Department of Chemistry, Rajaram College, Kolhapur 416004, India.)
الکلمات المفتاحية: Microwave irradiation, 2-Aminothiophenol, 2-Aminophenol, Acacia concinna, 2-Arylbenzothia/(oxa)zoles,
ملخص المقالة :
The expeditious synthesis of 2-aryl-benzothia/(oxa)zoles was carried out by the condensation of 2-aminothiophenol/2-aminophenol and diverse aryl aldehydes in presence of Acacia concinna as a biocatalyst under microwave irradiation. The catalytic process is associated with excellent yields, greener reaction conditions and the environmentally friendly microwave technique which are the striking features of the present protocol.
[1] S.A. Sarode, J.M. Bhojane, J.M. Nagarkar, Tetrahedron Lett. 56 (2015) 206-210.
[2] J. Ma, G. Bao, L. Wang, W. Li, B. Xu, B. Du, J. Lv, X. Zhai, P. Gong, Eur. J. Med. Chem. 96 (2015) 173-186.
[3] E. Chugunova, C. Boga, I. Sazykin, S. Cino, G. Micheletti, A. Mazzanti, M. Sazykina, A. Burilov, L. Khmelevtsova, N. Kostina, Eur. J. Med. Chem. 93 (2015) 349-359.
[4] S. Daravath, M.P. Kumar, A. Rambabu, N. Vamsikrishna, N. Ganji, Shivaraj, J. Mol. Struct. 1144 (2017) 147-158.
[5] A. Sairaman, F.C. Cardoso, A. Bispat, R.J. Lewis, P.J. Duggan, K.L. Tuck, Bioorg. Med. Chem. 26 (2018) 3046-3059.
[6] D. Gandhi, D.K. Agarwal, P. Kalal, A. Bhargava, D. Jangid, S. Agarwal, Phosphorus Sulfur Silicon Relat Elem. 193 (2018) 840-847.
[7] V.S. Padalkar, B.N. Borse, V.D. Gupta, K.R. Phatangare, V.S. Patil, P.G. Umape, N. Sekar, Arab. J. Chem. 9 (2016) S1125-S1130.
[8] Y. Li, Q. Hu, C.H. Chen, X.L. Wang, D.W. Gao, Bioresour. Technol. 236 (2017) 1-10.
[9] F.M. Shaikh, N.B. Patel, G. Sanna, B. Busonera, P.L. Colla, D.P. Rajani, J. Med. Chem. 24 (2015) 3129-3142.
[10] Y.H. Cho, C.Y. Lee, C.H. Cheon, Tetrahedron 69 (2013) 6565-6573.
[11] G.M. Ziarani, A. Badiei, M.S. Nahad, M. Hassanzadeh, Eur. J. Chem. 3 (2012) 433-436.
[12] H.L. Ruise, H.B. Ortega, S.R. Lima, R. Santillan, N. Farfan, Tetrahedron Lett. 52 (2011) 4308-4312.
[13] M. Sayyahi, M. Gorjizadeh, S. Sayyahi, Iran. J. Catal. 8 (2018) 203-211.
[14] A.V. Borhade, B.K. Uphade, Iran. J. Catal. 6 (2016) 197-201.
[15] R.D. Viirre, G. Evindar, R.A. Batey, J. Org. Chem. 73 (2008) 3452-3459.
[16] M. Radi, S. Saletti, M. Botta, Tetrahedron Lett. 49 (2008) 4464-4466.
[17] R. Wang, X.X. Lub, X.Q. Yu, L. Shi, Y. Sun, J. Mol. Catal. A: Chem. 266 (2007) 198-201.
[18] F.M. Moghaddam, G.R. Bardajee, H. Ismaili, S.M.D. Taimoory, Synth. Commun. 36 (2006) 2543-2548.
[19] P. Bandyopadhyay, M. Sathe, S. Ponmariappan, A. Sharma, P. Sharma, A.K. Srivastava, M.P. Kaushik, Bioorg. Med. Chem. Lett. 21 (2011) 7306-7309.
[20] T. Jadhav, B. Dhokale, S.M. Mobin, R. Misra, RSC Adv. 5 (2015) 29878-29884.
[21] R.M.F. Batista, S.P.G. Costa, M.M.M. Raposo, Tetrahedron Lett. 45 (2004) 2825-2828.
[22] B.B.F. Mirjalili, A. Bamoniri, M.A. Mirhoseinia, Iran. J. Catal. 6 (2016) 23-27.
[23] M. Zendehdel, K. Khosravi, M. Javadizadeh, Iran. J. Catal. 5 (2015) 333-337.
[24] B. Maleki, M. Baghayeri, S. M. Vahdat, A. Mohammadzadeh, S. Akhoondi, RSC Adv. 5 (2015) 46545-46551.
[25] B. Maleki, H. Salehabadi, M. K. Moghaddam, Acta Chim. Slov. 57 (2010) 741–745.
[26] B. Maleki, Collect. Czech. Chem. Commun. 76 (2011) 27-37.
[27] M. Okimoto, T. Yoshida, M. Hoshi, K. Hottori, M. Komata, K. Tomozawa, T. Chiba, Heterocycles 75 (2008) 35-42.
[28] T.G. Deligeorgiev, S. Kaloyanova, A. Vasilev, J.J. Vaquero, Phosphorus Sulfur Silicon Relat. Elem. 185 (2010) 2292-2302.
[29] D. Azarifar, B. Maleki, M. Setayeshnazar, Phosphorus Sulfur Silicon Relat. Elem. 184 (2009) 2097-2102.
[30] S. Pal, G. Patra, S. Bhunia, Synth. Commun. 39 (2009) 1196-1203.
[31] A.D. Kreuder, T. House-Knight, J. Whitford, E. Ponnusamy, P. Miller, N. Jesse, R. Rodenborn, S. Sayag, M. Gebel, I. Aped, I. Sharfstein, E. Manaster, I. Ergaz, A. Harris, L.N. Grice, ACS Sustainable Chem. Eng. 5 (2017) 2927-2935.
[32] C.O. Kappe, D. Dallinger, Nat. Rev. Drug Discovery 5 (2006) 51-63.
[33] X. Du, L. Zhao, X. He, H. Chen, W. Fang, W. Li, Chem. Eng. Sci. 160 (2017) 72-79.
[34] H.V. Chavan, B.P. Bandgar, ACS Sustainable Chem. Eng. 1 (2013) 929-936.
[35] R. Gupta, P.K. Sahu, P.K. Sahu, S.K. Srivastava, D.D. Agarwal, Catal. Commun. 92 (2017) 119-123.
[36] P. Wang, S. Tang, A. Lei, Green Chem. 19 (2017) 2092-2095.
[37] Y. Kawashita, M. Hayashi, Molecules 14 (2009) 3073-3093.
[38] L. Ackermann, S. Barfusser, J. Pospech, Org. Lett. 12 (2010) 724-726.
[39] K.R. Kumar, P.V.V. Satyanarayana, B.S. Reddy, Der Pharma Chem. 4 (2012) 761-766.
[40] H. Sharghi, M. Aberi, M.M. Doroodmand, J. Iran. Chem. Soc. 9 (2012) 189-204.
[41] A.K. Chakraborti, S. Rudrawar, K.B. Jadhav, G. Kaur, S.V. Chankeshwara, Green Chem. 9 (2007) 1335-1340.
[42] A. Teimouri, A.N. Chermahini, H. Salavati, L. Ghorbanian, J. Mol. Catal. A: Chem. 373 (2013) 38-45.
[43] R. Daengngern, N. Kungwan, J. Lumin. 167 (2015) 132-139.
[44] S. Rostamizadeh, S.A. Housaini, Phosphorus Sulfur Silicon Relat. Elem. 180 (2005) 1321-1326.
[45] R.S. Pottorf, N.K. Chada, M. Katekevics, V. Ozola, V. Suna, H. Ghane, T. Regberg, M.R. Player, Tetrahedron Lett. 44 (2003) 175-178.
[46] M. Kidwai, V. Bansal, A. Saxena, S. Aerryb, S. Mozumdarb, Tetrahedron Lett. 47 (2006) 8049-8053.
[47] G.F. Chen, H.M. Jia, L.Y. Zhang, B.H. Chen, J.T. Li, Ultrason. Sonochem. 20 (2013) 627-632.
[48] K. Bahrami, Z. Karami, J. Exp. Nanosci. 13 (2018) 272-283.
[49] D. Dev, J. Chandra, N.B. Palakurthy, K. Thalluri, T. Kalita, B. Mandal, Asian J. Org. Chem. 5 (2016) 663-675.
[50] V.S. Padalakar, V.D. Gupta, V.S. Patil, K.R. Phatangare, P.G. Umape, N. Sekar, Green Chem. Lett. Rev 5 (2012) 139-145.
[51] J.Y. Hwang, Y.D. Gong, J. Comb. Chem. 8 (2006) 297-303.
[52] Y. Wang, K. Sarris, D.R. Sauer, S.W. Djuric, Tetrahedron Lett. 47 (2006) 4823-4826.
[53] D. Suresh, A. Dhakshinamoorthy, K. Pitchumani, Tetrahedron Lett. 54 (2013) 6415-6419.
[54] Y.M. Ha, J.Y. Park, Y.J. Park, D. Park, Y.J. Choi, J.M. Kim, E.K. Lee, Y.K. Han, J.-A. Kim, J.Y. Lee, H.R. Moon, H.Y. Chung, Bioorg. Med. Chem. Lett. 21 (2011) 2445-2449.
