[Et3NH][HSO4] catalyzed one-pot synthesis of 14-aryl-14H-dibenzo[a,j] xanthenes under solvent-free conditions
الموضوعات : Iranian Journal of CatalysisZhongqiang Zhou 1 , Xiaocui Deng 2 , Xiaoyun Hu 3
1 - College of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan 430074, P. R. China.
2 - College of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan 430074, P. R. China.
3 - College of Chemistry and Materials Science, South-Central University for Nationalities, Wuhan 430074, P. R. China.
الکلمات المفتاحية: 2-Naphthol, Aldehyde, Solvent-free conditions, 14-Aryl-14H-dibenzo[a, j]xanthenes, [Et3NH][HSO4],
ملخص المقالة :
A simple and environmentally benign procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes by a one-pot condensation of 2-naphthol with aromatic aldehyde in the presence of [Et3NH][HSO4] as an acidic ionic liquid catalyst under solvent-free conditions has been developed. The reaction work-up is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions.
[1] A.M. El-Brashy, M.E. Metwally, F.A. El-Sepai, II Farmaco, 59 (2004) 809-817.
[2] J.M. Jamison, K. Krabill, A. Hatwalkar, Cell Biol. Int. Rep., 14 (1990) 1075-1084.
[3] K. Chibale, M. Visser, D.V. Schalkwyk, P.J. Smith, A. Saravanamuthu, A.H. Fairlamb, Tetrahedron, 59 (2003) 2289-2296.
[4] B.B. Bhowmik, P. Ganguly, Spectrochim Acta A: Mol. Biomol. Spectrosc., 61 (2005) 1997-2003.
[5] C.G. Knight, T. Stephens, Biochem. J., 258 (1989) 683-689.
[6] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, J. Phys. D: Appl. Phys., 35 (2002) 1473-1476.
[7] R.J. Sarma, J.B. Baruah, Dyes Pigments, 64 (2005) 91-92.
[8] R. Kumar, G.C. Nandi, R.K. Verma, M.S. Singh, Tetrahedron Lett., 51 (2010) 442-445.
[9] G. Luo, D. Liu, C. Liu, Prep. Biochem. Biotech., 38 (2008) 265-270.
[10] K. Amir, D. Abolghasem, B. Mehdi, T.H. Niloofar, Z.D. Mohsen, Chin. J. Chem., 29 (2011) 297-302.
[11] F.Q. Ding, L.T. An, J.P. Zou, Chin. J. Chem., 25 (2007) 645-648.
[12] H.R. Shaterian, M. Ghashang, A. Hassankhani, Dyes Pigments, 76 (2008) 564-568.
[13] J.V. Madhav, Y.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kuarm, P.A. Crooks, B. Rajitha, J. Mol. Catal. A: Chem., 304 (2009) 85-87.
[14] F. Shirini, N.G. Khaligh, Dyes Pigments, 95 (2012) 789-794.
[15] D. Liu, Y. Yu, W. Shi, C. Liu, G. Luo, Prep. Biochem. Biotech., 37 (2007) 77-81.
[16] W. Su, D. Yang, C. Jin, B. Zhang, Tetrahedron Lett., 49 (2008) 3391-3394.
[17] S. Urinda, D. Kundu, A. Majee, A. Hajra, Heteroatom Chem., 20 (2009) 232-234.
[18] L. Nagarapu, S. Kantevari, V.C. Mahankhali, S. Apuri, Catal. Commun., 8 (2007) 1173-1177.
[19] G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani, Z. Emdadi, Ultrason. Sonochem., 16 (2009) 7-10.
[20] A. Zarei, A.R. Hajipour, L. Khazdooz, Dyes Pigments, 85 (2010) 133-138.
[21] N.G. Khaligh, Ultrason. Sonochem., 19 (2012) 736-739.
[22] G.B.D. Rao, M.P. Kaushik, A.K. Halve, Tetrahedron Lett., 53 (2012) 2741-2744.
[23] G.M. Ziarani, A.R. Badiei, M. Azizi, Scientia Iranica C, 18 (2011) 453-457.
[24] M. Mokhtary, S. Refahati, Dyes Pigments, 99 (2013) 378-381.
[25] K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, Dyes Pigments, 80 (2009) 30-33.
[26] P. Kumari, V. Yathindranath, S.M.S. Chauhan, Synth. Commun., 38 (2008) 637-648.
[27] A. Zare-Bidaki, A. Davoodnia, Bull. Korean Chem. Soc., 33 (2012) 1154-1158.
[28] D. Fang, Z.L. Liu, J. Heterocycl. Chem., 47 (2010) 509-512.
[29] A.R. Hajipour, Y. Ghayeb, N. Sheikhan, E. Arnold, A.E. Ruohoa, Synlett, (2010) 741-744.
[30] R. Tayebee, S. Tizabi, Chin. J. Catal., 33 (2012) 962-969.
[31] R. Fareghi-Alamdari, M. Golestanzadeh, F. Agend, N. Zekri, Comptes Rendus Chimie, 16 (2013) 878-887.
[32] F. Shirini, M. Abedini, R. Pourhasan, Dyes Pigments, 99 (2013) 250-255.
[33] V.I. Parvulescu, C. Hardacre, Chem. Rev., 107 (2007) 2615-2665.
[34] C. Wang, L. Guo, H. Li, Y. Wang, J. Weng, L. Wu, Green Chem., 8 (2006) 603-607.
