Betaine hydrochloride (BHC) catalyzed synthesis of 4-thiazolidinones derivatives
الموضوعات : Iranian Journal of CatalysisAmol Khandebharad 1 , Swapnil Sarda 2 , Charansingh Gill 3 , Brijmohan Agrawal 4
1 - Department of Chemistry, J. E. S. College, Jalna, (Maharashtra) India.
2 - Department of Chemistry, J. E. S. College, Jalna, (Maharashtra) India.
3 - Department of Chemistry, Dr. B.A.M. University, Aurangabad, (Maharashtra) India.
4 - Department of Chemistry, J. E. S. College, Jalna, (Maharashtra) India.
الکلمات المفتاحية: Aromatic aldehydes, Betaine hydrochloride (BHC), 4-Thiazolidinediones, Aromatic amines, Memercaptoacetic acid,
ملخص المقالة :
Betaine hydrochloride (BHC), as an ionic salt was found to be an efficient and recyclable catalyst for the one-pot synthesis of 4-thiazolidinediones. The methodology of study was achieved by one-pot condensation of aromatic aldehydes, aromatic amine and mercaptoacetic acid in the presence of betaine hydrochloride (BHC) at reflux temperature in ethanol as solvent. The efficiency of Betaine hydrochloride has been compared with all aspects of reaction conditions such as temperature, solvent and amount of the catalyst. This method excludes the use of heavy metal catalyst, tedious work-up and affords excellent yields of product. These advantages makes the technique greener and superior as compare to other reported methods.
[1] R.C. Cioc, E. Ruijter, R.V.A. Orru, Green Chem. 16 (2014) 2958-2975.
[2] F.I. McGonagle, H.F. Sneddon, C. Jamieson, A.J.B. Watson, ACS Sustainable Chem. Eng. 2 (2014) 523-532.
[3] M.A. Mironov, QSAR Comb. Sci. 25 (2006) 423-431.
[4] E.L. Smith, A.P. Abbott, K.S. Ryder, Chem. Rev. 114 (2014) 11060-11082.
[5] D. Azarifar, M. Golbaghi, R. Nejat-Yami, Iran. J. Catal. 26 (2014) 8291-8294.
[6] S. Rostamizadeh, N. Zekri, Iran. J. Catal. 4 (2014) 253-260.
[7] A. Hullio, G.M. Mastoi, Iran. J. Catal. 1 (2011) 79-86.
[8] S.R. Sarda, J.D. Kale, S.K. Wasmatkar, V.S. Kadam, P.G. Ingole, W.N. Jadhav, R.P. Pawar, Mol. Divers. 13 (2009) 545-549.
[9] S.R. Sarda, W.N. Jadhav, A.S. Shete, K.B. Dhopte, S.M. Sadawarte, P.J. Gadge, R.P. Pawar, Synth. Commun. 40 (2010) 2178-2184.
[10] M. Lever, W. Atkinson, P.M. George, S.T. Chambers, Clin. Biochem. 40 (2007) 798-801.
[11] R. Likes, R.L. Madl, S.H. Zeisel, S.A.S. Craig, J. Cereal Sci. 46 (2007) 93-95.
[12] F. Goursaud, T. Benvegnu, Carbohydr. Res. 344 (2009) 136-139.
[13] K.D.O. Vigier, A. Benguerba, J. Barrault, F. Jérôme, Green Chem. 14 (2012) 285-289.
[14] F. Liu, F. Boissou, A. Vignault, L. Lemme, S. Marnikovic, B. Estrine, K.D.O. Vigier, F. Jerome, RSC Adv. 4 (2014) 28836-28841.
[15] N. Araji, D.D. Manjiza, G. Chatel, A. Moores, F. Jerome, K.D.O. Vigier, Green Chem. 19 (2017) 98-101.
[16] A. Zhu, R. Liu, C. Du, L. Li, RSC Adv. 7(2017) 6679-6684.
[17] M. Vigorita, R. Vottana, F. Monforte, R. Maccari, M.T. Monforte, A. Trovato, M.F. Taviano, N. Miceli, G.D. Luca, S. Alcaro, F. Ortuso, Bioorg. Med. Chem. 11 (2003) 999-1006.
[18] R.K. Rawal, R. Tripathi, S.B. Katti, C. Pannecouque, E. De Clercq, Eur. J. Med. Chem. 43 (2008) 2800-2806.
[19] K. Omar, A. Geronikaki, P. Zoumpoilakis, C. Camoutsis, M. Sokovic, A. Ciric, J. Gamoclija, Bioorg. Med. Chem. 18 (2010) 426-432.
[20] A.A. El-Barbary, A.I. Khodair, E.B. Pedersen, C. Nielsen, Monatsh. Chem. 125 (1994) 593-598.
[21] O. Guezel, A. Salman, J. Enzyme Inhib. Med. Chem. 24 (2009) 1015-1023.
[22] R. Ottanà, R. Maccari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Paola, L. Sautebin, S. Cuzzocrea, M.G. Vigorita, Bioorg. Med. Chem. 13 (2005) 4243-4252.
[23] S.K. Srivastava, S. Srivastava, S.D. Srivastava, Indian J. Chem. 41 (2002) 1937-1945.
[24] G. Küçükgüzel, A. Kocatepe, E. De Clercq, F. Şahin, M. Güllüce, Eur. J. Med. Chem. 41 (2006) 353-359.
[25] N.B. Patel, F.M. Shaikh, Saudi Pharm. J. 18 (2010) 129-136.
[26] D. Havrylyuk, L. Mosula, B. Zimenkovosky, O. Vasylenko, A. Gzella, R. Lesyk, Eur. J. Med. Chem. 45 (2010) 5012-5021.
[27] B.K. Matharu, M.R. Manrao, V.K. Kaul, Indian J. Heterocycl. Chem. 15 (2005) 95-96.
[28] H. Chen, Q. Yin, C. Li, E. Wang, F. Gao, X. Zhang, Z. Yin, S. Wei, X. Li, M. Meng, P. Zhang, N. Li, J. Zhang, ACS Med. Chem. Lett. 2 (2011) 845-848.
[29] J. Tierney, J. Heterocycl. Chem. 26 (1989) 997-1001.
[30] H.R. Ma, Y.H. Hou, Y.J. Bai, J. Lu, B.Q. Yang, J. Organomet. Chem. 637 (2001) 742-744.
[31] T. Srivastava, W. Haq, S.B. Katti, Tetrahedron. 58 (2002) 7619-7624.
[32] X. Xing, F. Kui, P. Haixia, W. Yang, J. Yang, S. Wei, X. Zhengfeng, H. Yonghai, Chin. J. Org. Chem. 36 (2016) 1942-1947.
[33] N. Foroughifar, S. Ebrahimi, Chin. Chem. Lett. 24 (2013) 389-391.
[34] D. Prasad, M. Nath, J. Heterocycl. Chem. 49 (2012) 628-633.
[35] M.D. Shanti, K. Shanti, J. Meshram, Phosphorus Sulfur Silicon Relat. Elem. 188 (2013) 1351-1360.
[36] M.P. Thakare, P. Kumar, N. Kumar, S.K. Pandey, Tetrahedron Lett. 55 (2014) 2463-2466.
[37] R.R. Harale, P.V. Shitre, B.R. Sathe, M.S. Shingare, Res. Chem. Intermed. 42 (2016) 6695-6703.
[38] M.A. Chaudhari, J.B. Gujar, D.S. Kawade, P.V. Shinde, M.S. Shingare, Res. Chem. Intermed. 41 (2015) 10027-10035.
[39] H. Varshney, A. Ahmad, N.N. Farshori, A. Ahamad, A. U. Khan, A. Rauf, Med. Chem. Res. 22 (2013) 3204-3212.
[40] A.S. Nagarajan, S. Kamalraj, J. Muthumary, B.S.R. Reddy, Indian J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 48 (2009) 1577-1582.
[41] U.P. Singh, H.R. Bhat, M.K. Kumawat, R.K. Singh, SpringerPlus 2 (2013) 1-11.
[42] D. Prasad, A. Preetam, M. Nath, RSC Adv. 2 (2012) 3133-3140.
[43] H. Zheng, Y.J. Mei, K. Du, Q.Y. Shi, P.F. Zhang, Catal. Lett. 143 (2013) 298-301.
[44] U.R. Pratap, D.V. Jawale, M.R. Bhosle, R.A. Mane, Tetrahedron Lett. 52 (2011) 1689-1691.
[45] S. Ahmadi, D. Ghazanfari, Iran. J. Catal. 3 (2013) 177-181.
[46] L.D. Khillare, M.R. Bhosle, A.R. Deshmukh, R.A. Mane, Res. Chem. Intermed. 41 (2015) 8955-8964.
[47] X. Zhang, X. Li, D. Li, G. Qu, J. Wang, P.M. Loiseau, X. Fan, Bioorg. Med. Chem. Lett. 19 (2009) 6280-6283.
