Morpholinium glycolate as an efficient and reusable catalyst for the synthesis of bis(pyrazol-5-ol) derivatives under solvent-free conditions

Subject Areas : Iranian Journal of Catalysis

Mohd Akmal Shaikh ¹ (Post Graduate and Research Centre, Maulana Azad College, Aurangabad-431001(M.S), India.)
Mazahar Farooqui ² (Dr. Rafiq Zakaria College for Women, Aurangabad-431001 (M.S), India.)
Syed Abed ³ (Government College of Arts and Science, Aurangabad- 431001 (M.S), India.)

Received: 2017-08-25 Accepted : 2018-02-28 Published : 2018-06-01

Keywords:

References:

[1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
[2] L.F. Tietze, A. Modi, Med. Res. Rev. 20 (2000) 304-322.
[3] I. Ugi, A. Domling, B. Werner, J. Heterocycl. Chem. 37 (2000) 647-658.
[4] K. Tanaka, G. Kaupp, Solvent-free organic synthesis, John Wiley & Sons, 2009.
[5] T. Welton, Chem. Rev. 99 (1999) 2071-2084.
[6] P. Walden, Bull. Acad. Imper. Sci. St. Petersburg 1800 (1914) 405-422.
[7] M.J. Earle, K.R. Seddon, Pure Appl. Chem. 72 (2000) 1391-1398.
[8] N.V. Plechkova, K.R. Seddon, Ionic Liquids: "Designer" Solvents for Green Chemistry, in: Methods and Reagents for Green Chemistry: An Introduction, 2007, pp. 103-130.
[9] P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3773-3789.
[10] C.M. Gordon, Appl. Catal. A 222 (2001) 101-117.
[11] D. Zhao, M. Wu, Y. Kou, E. Min, Catal. Today 74 (2002) 157-189.
[12] V.I. Pârvulescu, C. Hardacre, Chem. Rev. 107 (2007) 2615-2665.
[13] K. Biswas, C.N.R. Rao, Chem. Eur. J. 13 (2007) 6123-6129.
[14] T. Ichikawa, M. Yoshio, A. Hamasaki, T. Mukai, H. Ohno, T. Kato, J. Am. Chem. Soc. 129 (2007) 10662-10663.
[15] P. Hapiot, C. Lagrost, Chem. Rev. 108 (2008) 2238-2264.
[16] F. van Rantwijk, R.A. Sheldon, Chem. Rev. 107 (2007) 2757-2785.
[17] H. Zhao, Chem. Eng. Commun. 193 (2006) 1660-1677.
[18] X. Han, D.W. Armstrong, Acc. Chem. Res. 40 (2007) 1079-1086.
[19] J.G. Huddleston, H.D. Willauer, R.P. Swatloski, A.E. Visser, R.D. Rogers, Chem. Commun. (1998) 1765-1766.
[20] H. Zhao, S. Xia, P. Ma, J. Chem. Technol. Biotechnol. 80 (2005) 1089-1096.
[21] J. Pernak, N. Borucka, F. Walkiewicz, B. Markiewicz, P. Fochtman, S. Stolte, S. Steudte, P. Stepnowski, Green Chem. 13 (2011) 2901-2910.
[22] J. Elguero, P. Goya, N. Jagerovic, A.M.S. Silva, Targets Heterocycl. Syst. 6 (2002) 52-98.
[23] E. McDonald, K. Jones, P.A. Brough, M.J. Drysdale, P. Workman, Curr. Top. Med. Chem. 6 (2006) 1193-1203.
[24] M.A. Zolfigol, A. Khazaei, F. Karimitabar, M. Hamidi, Appl. Sci. 6 (2016) 1-9.
[25] P.C. Lv, J. Sun, Y. Luo, Y. Yang, H.L. Zhu, Bioorg. Med. Chem. Lett. 20 (2010) 4657-4660.
[26] G. Mariappan, B.P. Saha, L. Sutharson, A. Haldar, Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 49 (2010) 1671-1674.
[27] D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. DeFelice, M.E. Feigenson, J. Med. Chem. 28 (1985) 256-260.
[28] G. Mariappan, B.P. Saha, L. Sutharson, A. Singh, S. Garg, L. Pandey, D. Kumar, Saudi Pharm. J. 19 (2011) 115-122.
[29] L.C. Behr, R. Fusco, C.H. Jarboe, The Chemistry of Heterocyclic Compounds, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles, and Condensed Rings, A. Weissberger, (Ed.); Interscience, New York, 1967.
[30] D. Castagnolo, A. De Logu, M. Radi, B. Bechi, F. Manetti, M. Magnani, S. Supino, R. Meleddu, L. Chisu, M. Botta, Bioorg. Med. Chem. 16 (2008) 8587-8591.
[31] M. Londershausen, Pestic. Sci. 48 (1996) 269-292.
[32] D. Singh, D. Singh, J. Indian Chem. Soc. 68 (1991) 165-167.
[33] C. Pettinari, F. Marchetti, R. Pettinari, A. Drozdov, S. Troyanov, A.I. Voloshin, N.M. Shavaleev, J. Chem. Soc. Dalton Trans. (2002) 1409-1415.
[34] H. Banari, H. Kiyani, A. Pourali, Res. Chem. Intermed. 43 (2017) 1635-1649.
[35] S.J. Saghanezhad, M.H. Sayahi, I. Imanifar, M. Mombeni, S. Deris Hamood, Res. Chem. Intermed. 43 (2017) 6521–6536.
[36] A. Das Gupta, R. Pal, A.K. Mallik, Green Chem. Lett. Rev. 7 (2014) 404-411.
[37] W. Wang, S.X. Wang, X.Y. Qin, J.T. Li, Synth. Commun. 35 (2005) 1263-1269.
[38] S. Tayebi, K. Niknam, Iran. J. Catal. 2 (2012) 69-74.
[39] F. Shirini, M. Seddighi, M. Mazloumi, M. Makhsous, M. Abedini, J. Mol. Liq. 208 (2015) 291-297.
[40] E. Kolvari, N. Koukabi, M.M. Hosseini, J. Mol. Catal. A: Chem. 397 (2015) 68-75.
[41] Z. Zhou, Y. Zhang, J. Chil. Chem. Soc. 60 (2015) 2992-2996.
[42] A.R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, O. Khaledian, B.S. Shaghasemi, Res. Chem. Intermed. 42 (2016) 4759-4772.
[43] N.G. Khaligh, S.B.A. Hamid, S.J.J. Titinchi, Chin. Chem. Lett. 27 (2016) 104-108.
[44] A. Khazaei, F. Abbasi, A.R. Moosavi-Zare, New J. Chem. 38 (2014) 5287-5292.
[45] Z. Zhou, Y. Zhang, Green Chem. Lett. Rev. 7 (2014) 18-23.
[46] D. Banerjee, R. Karmakar, U. Kayal, G. Maiti, Synth. Commun. 47 (2017) 1006-1012.
[47] M. Fatahpour, F. Noori Sadeh, N. Hazeri, M.T. Maghsoodlou, M. Lashkari, J. Iran. Chem. Soc. 14 (2017) 1945-1956.
[48] P.S. Mahajan, M.D. Nikam, V. Khedkar, P. Jha, P.V. Badadhe, C.H. Gill, J. Heterocycl. Chem. 54 (2017) 1109-1120.
[49] S. Sobhani, F. Zarifi, J. Skibsted, ACS Sustainable Chem. Eng. 5 (2017) 4598-4606.
[50] M. Xing, T.T. Zhao, Y.J. Ren, N.N. Peng, X.H. Yang, X. Li, H. Zhang, G.Q. Liu, L.R. Zhang, H.L. Zhu, Med. Chem. Res. 23 (2014) 3274-3286.
[51] S. Abed, S.M. Akmal, N. Ali, M. Farooqui, Chem. Sci. Int. J. 17 (2016) 1-8.