Li(OHCH2CH2NH2)(CF3OAC): A novel and homogeneous acidic ionic liquid catalyst for efficient synthesis of 2-amino-4H-chromene derivatives

Document Type: Articles

Authors

1 Young Researchers and Elites Club, Ardabil Branch, Islamic Azad University, Ardabil, Iran.

2 Young Researchers and Elites Club, Rasht Branch, Islamic Azad University, Rasht, Iran.

Abstract

The ionic liquid Li(OHCH2CH2NH2)(CF3OAC) was found to efficiently catalyze the three-component reaction between different enols, aldehydes, and malononitrile , leading to rapid synthesis of 2-amino-4H-chromene derivatives in fairly high yields. The catalyst is easily prepared, highly stable, simple to handle and recycled for several times without significant loss of activity. The method is simple, starts from readily accessible commercial starting materials, and provides biologically interesting products in good yields and short reaction times. The desired ionic liquids, for aromatic aldehyde leads to get the products. Heating was very effective in increasing the efficiency of the product and in the presence of heat, the desired products were created in a shorter time.

Keywords


[1] A.S.H. Salem, H.S. Hamid, Chem. Eng. Technol. 20 (1997) 342-347.
[2] P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772-3789.
[3] T. Welton, Chem. Rev. 248 (2004) 2459-2477.
[4] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998, p. 30.
[5] S.T. Handy, Chem. Eur. J. 9 (2003) 2938-2944.
[6] P. Luis, A. Garea, A.J. Irabien, J. Membr. Sci. 330 (2009) 80-89.
[7] C. Hardacre, J. Holbrey, M. Nieuwenhuyzen, T.G.A. Youngs, Acc. Chem. Res. 40 (2007) 1146-1155.
[8] V.I. Parvulescu, C. Hardacre, Chem. Rev. 107 (2007) 2615-2665.
[9] S.M.S. Chauhan, S. Agarwal, P. Kumari, Synth. Commun. 37 (2007) 2917-2925.
[10] Z. Dong, X. Liu, J. Feng, M. Wang, L. Lin, X. Feng, Eur. J. Org. Chem. 2011 (2011) 137-142.
[11] L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28 (1993) 517-520.
[12] A. Shaabani, S. Samadi, Z. Badri, A. Rahmati, Catal. Let. 104 (2005) 39-43.
[13] M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A: Chem. 359 (2012) 74-80.
[14] J.M. Khurana, S. Kumar, Tetrahedron Lett. 50 (2009) 4125-4127.
[15] H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7 (2010) 890-894.
[16] M.J. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
[17] M.M. Heravi, B. Alimadadi, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10 (2008) 272-275.
[18] S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48 (2007) 3299-3303.
[19] H.J. Wang, J. Lu, Z.H. Zhang, Monatsh. Chem. 141 (2010) 1107-1112.
[20] H. Mehrabi, M. Kazemi, Chin. Chem. Lett. 22 (2011) 1419-1422.
[21] K. Tabatabaeian, H. Heidari, M. Mamaghani, N.O. Mahmoodi, Appl. Organomet. Chem. 26 (2012) 56-61.
[22] K. Rad-Moghadam, S.C. Azimi, E. Abbaspour-Gilandeh, Tetrahedron Lett. 54 (2013) 4633-4636.
[23] E. Abbaspour-Gilandeh, S.C. Azimi, K. Rad-Moghadam, A. Mohammadi-Barkchai, Iran. J. Catal. 3 (2013) 15-20
[24] A. Shaabani, S. Samadi, Z. Badri, A. Rahmati, Catal. Lett. 104 (2005) 39-43.
[25] W. Xiang-Shan, Z. Zhao-Sen, S. Da-Qing, W. Xian-Yong, Z. Zhi-Min, Chin. J. Org. Chem. 25 (2005) 1138-1141.
[26] M. Seifi, H. Sheibani. Catal. Lett. 126 (2008) 275-279.
[27] S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi. Synth. Commun. 37 (2007) 1097-1108.
[28] L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu. J. Fluorine Chem. 127 (2006) 97-100.
[29] T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang, T.S. Li. Synlett 5 (2004) 871-873.
[30] R. Hekmatshoar, S. Majedi, K. Bakhtiari. Catal. Commun. 9 (2008) 307-310.
[31] Y.A. Sharanin, A.M. Shestopalov. Zh. Org. Khim. 25 (1989) 1331-1335.
[32] J.-C. Xu, W.-M. Li, H. Zheng, L. Yi-Feng, P.-F. Zhang, Tetrahedron 67 (2011) 9582–9587.
[33] M. Hong, C. Cai, J. Chem. Res. 34 (2010) 568-570.
[34] S. Gowravaram, K. Arundhathi, K.B.S. Sudhakar, J.S. Yadav, Synth. Commun. 39 (2009) 433-442;
[35] M.J. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
[36] Y. Yi, G. Hongyun, L. Xiaojun, J. Heterocycl. Chem. 48 (2011) 1264-1268.
[37] A. Shaabani, R. Ghadari, S. Ghasemi, M. Pedarpour, A.H. Rezayan, A. Sarvary, S.W. Ng, J. Comb. Chem. 11 (2009) 956–959.
[38] X.H. Wang, X.H. Zhang, S.J. Tu, F. Shi, X. Zou, S. Yan, Z.G. Han, W.J. Hao, X.D. Cao, S.S. Wua, J. Heterocycl. Chem. 46 (2009) 832–836.
[39] Y. Yu, H. Guo, X. Li, J. Heterocycl. Chem. 48 (2011) 1264–1268.