A green procedure for synthesis of xanthene derivatives: Micellar solution of sodium dodecylphosphonate catalyzes condensation reaction of aldehydes and β-naphthol in aqueous media

Iranian Journal of Catalysis

مقاله 7، دوره 4، شماره 1، خرداد 2014، صفحه 49-53   

نویسندگان

Razieh Ghashghaei؛ Soheila Ghassamipour^*

Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran

چکیده

A green and convenient méthode for the synthesis of  a variety of xanthene derivatives by condensation reaction between aldehydes and β-naphthol or dimedone in an micellar solution of sodium dodecylphosphonate is described. This method offers several advantages, such as using of a cheap and environmentally benign reaction media, low loadings of sodium dodecylphosphonate as catalyst and easy work-up.

کلیدواژه‌ها

β-naphthol؛ Dimedone؛ Adehydes؛ Micellar media؛ Sodium dodecylphosphonate؛ Xanthenes

مراجع

[1] K. Singh, D. Arora, S. Singh, Tetrahedron Lett., 47 (2006) 4205-4207.

[2] S. Ko, C.F. Yao, Tetrahedron Lett., 47 (2006) 8827-8829.

[3] R.J. Sarma, J.B. Baruah, Dyes Pigments, 64 (2005) 91-92.

[4] (a) O. Sirkeeioglu, N. Talinli, A. Akar, J. Chem. Res.(S), (1995) 502-506; (b) M. Ahmad, T. A. King, D.O. Ko, B.H. Cha, J. Lee, J. Phys. D: Appl. Phys., 35 (2002) 1473-1476.

[5] J.P. Bacci, A.M. Kearney, D.L. Van Vranken, J. Org. Chem., 70 (2005) 9051-9053.

[6] C.G. Knight, J. Biochem., 258 (1989) 683-687.

[7] K. Chibale, M.R. Visser, D. Van Schalkwyk, P.J. Smith. Tetrahedron, 59 (2003) 2289-2296.

[8] A. Jha, J. Beal, Tetrahedron Lett., 45 (2004) 8999-9001.

[9] C.W. Kuo, J.M. Fang, Synth. Commun., 31 (2001) 877-892.

[10] R.J. Sarma, J.B. Baruah, Dyes Pigments, 64 (2005) 91-92.

[11] A.R. Khosropour, M.M. Khodaei, H.A. Moghannian, Synlett, (2005) 955-958.

[12] B. Rajitha, B.S. Kumar, Y.T. Reddy, P. Reddy, N. Sreenivasulu, Tetrahedron Lett., 46 (2005) 8691-8693.

[13] A. Sharifi, S. Abaee, A. Tavakkoli, M. Mirzaei, A. Zolfagharei, Synth. Commun., 38 (2008) 2958-2966.

[14] S. Ko, C.F. Yao, Tetrahedron Lett., 47 (2006) 8827-8829.

[15] L. Nagarapu, S. Kantevari, V.C. Mahankhali, S. Apuri,  Catal. Commun., 8 (2007) 1173-1300.

[16] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhane, Iranian J. Catal., 1 (2011) 1-9.

[17] B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B. V. Rao, J. Mol. Catal. A Chem., 255 (2006) 74-82.

[18] M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun., 8 (2007) 1595-1598.

[19] A. Saini, S. Kumar, J. S. Sandhu, Synlett, (2006) 1928-1932.

[20] M.A. Bigdeli, M.M. Heravi, G. H. Mahdavinia, J. Mol. Catal. A Chem., 275 (2007) 25-29.

[21] M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, E. Arzroomchilar, Bioorg. Med. Chem. Lett., 18 (2008) 436-438.

[22] M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigments, 76 (2008) 836-839.

[23] S. Ghassamipour, A.R. Sardarian, Tetrahedron Lett., 50 (2009) 514-519.

[24] W. Su, K.D. Yang, C. Jin, B. Zhang, Tetrahedron Lett., 49 (2008) 3391-3394.

[25] M.N. Kalla Reddi, K. Balam Satheesh, A.K. Mungara, A. Palanisamy, L. Shaik. I.K. Ola, Molecules, 17 (2012) 7543-7555.

[26] R. Tayebee, S. Tizabi, Chin J Catal., 33 (2012) 962-969.

[27] A. Zare, M. Mokhlesi, A.R. Hasaninejad, T. Hekmat-Zadeh, E. J. Chem, 9 (2012) 1854-1863.

[28] G. Kakade, B. Madje, M. Ware, M. Shingare, Bull. Catal. Soc. India, 6 (2007) 99-103.

[29] B. Das, P. Thirupathi, K. Reddy, B. Ravikanth, L. Nagarapu, Catal. Commun., 8 (2007) 535-538.

[30] H.R. Shaterian, A. Hosseinian, M. Ghaghang, Tur. J. Chem., 33 (2009) 233-240.

[31] M. Naser-Esfahani, T. Abdizadeh, J. Chem. Sci. Technol. 2 (2013) 14-17.

[32] R. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Catal. A: Chem., 269 (2007) 53-57.

[33] C. Jiao, S. Jian, Y. Chaoguo, Chem. Res. Chin. Univ., 27 (2011) 49-50.

[34] S. Kantevari, R. Bantu, L. Nagarapu, Arkivoc, xvi (2006) 136-148.

[35] A. Javid, M.M. Heravi, F.F. Bamoharram, E. J. Chem., 8 (2011) 910-916.

[36] Z.H. Zhang, Y.H. Liu, Catal. Commun., 9 (2009) 1715-1719.

[37] M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, H.R. Tavakoli, Chin. Chem. Lett., 22 (2011) 9-12.

[38] M.J. Rosen J.T. Kunjappu, Surfactants and Interfacial Phenomena, ed. John Wiley & Sons Press, Hoboken, New Jersey, 2012.

[39] K. Murtagh, B.A. Sweetman, P.J. Guiry, Pure Appl. Chem., 78 (2006) 311-320.