Boric acid as a highly efficient and reusable catalyst for the one-pot synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions
الموضوعات : Iranian Journal of CatalysisSobhan Rezayati 1 , Rahimeh Hajinasiri 2 , Zahra Erfani 3 , Saman Rezayati 4 , Saeid Afshari-sharifabad 5
1 - Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran.
Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran.
2 - Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran.
3 - Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran.
4 - Department of Chemistry, Payame Noor University, PO BOX 19395-4697, Tehran, Iran.
5 - Chemistry Department, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran.
الکلمات المفتاحية: Dimedone, Xanthenes, Solid acid, Boric acid, Aromatic aldehyde, One-pot reaction,
ملخص المقالة :
An efficient and simple procedure for the synthesis of 1,8-dioxo-octahydroxanthenes from the aromatic aldehydes and 5,5-dimethylcyclohexane-1,3-dione (dimedone) in the presence of boric acid [BO3H3 or B(OH)3] as an inexpensive and reusable catalyst is described. The salient features of this methodology are: the elimination of corrosive liquid acids, high yields, simple methodology, short reaction times, easy work-up and green heterogeneous catalyst.
[1] J.M. Jamison, K. Krabill, A. Hatwalkar, Cell. Biol. Int. Rep. 14 (1990) 1075-1084.
[2] R.M. Ion, D. Frackowiak, K. Wiktorowicz, Acta Biochim. Pol. 45 (1998) 833-845.
[3] K. Muharrem, B. Erhan, C. Ferdag, Med. Chem. Res. 20 (2011) 1214-1219.
[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] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, G. Narcisse, G. Uchida Emouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67-71.
[7] M. Ahmad, T.A. King, Do-K. Ko, B.H. Cha, J. Lee. J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
[8] B. Rajitha, B. Sunil Kumar, Y. Thirupathi Reddy, P. Narsimha Reddy, N. Sreenivasulu, Tetrahedron Lett. 46 (2005) 8691-8693.
[9] A. Saini, S. Kumar, J.S. Sandhu, Synlett (2006) 1928-1932.
[10] S. Ko, C.F. Yao, Tetrahedron Lett. 47 (2006) 8827-8829.
[11] A.R. Khosropour, M.M. Khodaei, H. Moghannian, Synlett (2005) 955-958.
[12] M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, J. Mol. Catal. A: Chem. 275 (2007) 25-29.
[13] D.W. Knight, P.B. Little, J. Chem. Soc., Perkin Trans. 1. 14 (2001) 1771-1777.
[14] A. Jha, J. Beal, Tetrahedron Lett. 45 (2004) 8999-9001.
[15] C.W. Kuo, J.M. Fang, Synth. Commun. 31 (2001) 877-892.
[16] J.Q. Wang, R.G. Harvey, Tetrahedron 58 (2002) 5927-5931.
[17] M.M. Amini, M. Seyyedhamzeh, A. Bazgir, Appl. Catal. A: Gen. 323 (2007) 242-245.
[18] M.M. Heravi, K. Bakhtiari, Z. Daroogheha, F.F. Bamoharram, J. Mol. Catal. A: Chem. 273 (2007) 99-101.
[19] L. Nagarapu, S. Kantevari, V.C. Mahankhali, S. Apuri, Catal. Commun. 8 (2007) 1173-1177.
[20] M.A. Pasha, V.P. Jayashankara, Bioorg. Med. Chem. Lett. 17 (2007) 621-623.
[21] F.Q. Ding, L.T. An, J.P. Zou, Chin. J. Chem. 25 (2007) 645-648.
[22] H.R. Shaterian, M. Ghashang, A. Hassankhani, Dyes Pigm. 76 (2008) 564-568.
[23] M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigm. 76 (2008) 836-839.
[24] I.G. Shakibaei, P. Mirzaei, A. Bazgir, Appl. Catal. A:
Gen. 325 (2007) 188-192.
[25] H.R. Shaterian, A. Hosseinian, M. Ghashang, Turk. J. Chem. 33 (2009) 233-240.
[26] A.K. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A.R. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq. 167 (2012) 69-77.
[27] M. Dabiri, S.C. Azimi, A. Bazgir, Chem. Pap. 62 (2008) 522-526.
[28] A. Kumar, R.A. Maurya, Tetrahedron Lett. 49 (2008) 5471-5474.
[29] K.F. Shelke, S.B. Sapkal, S.S. Sonar, B.R. Madje, B.B. Shingate, M.S. Shingare, Bull. Korean Chem. Soc. 30 (2009) 1057-1060.
[30] K.F. Shelke, S.B. Sapkal, G.K. Kakade, P.V. Shinde, B.B. Shingate, M.S. Shingare, Chin. Chem. Lett. 20 (2009) 1453-1456.
[31] M. Hosseini-Sarvari, J. Iran. Chem. Soc. 8 (2011) 119-128.
[32] R. Ghorbani-Vaghei, S.M. Malaekehpoor, J. Iran. Chem. Soc. 7 (2010) 957-964.
[33] A.R. Hajipour, Y. Ghayeb, N. Sheikhan, J. Iran. Chem. Soc. 7 (2010) 447-454.
[34] B. Tamami, H. Firouzabadi, F. Ebrahimzadeh, A. Fadavi, J. Iran. Chem. Soc. 6 (2009) 722-728.
[35] A. Sharifi, M.S. Abaee, A. Tavakkoli, M. Mirzaei, J. Iran. Chem. Soc. 5 (2008) 113-117.
[36] R. Hajinasiri, S. Rezayati, Z. Naturforsch. 68b (2013) 818-822.
[37] D. Zareyee, P. Alizadeh, M.S. Ghandali, M.A. Khalilzadeh, Chem. Pap. 67 (2013) 713-721.
[38] S. Sajjadifar, S. Rezayati, Chem. Pap. 68 (2014) 531-539.
[39] B. Karimi, D. Zareyee, Org. Lett. 10 (2008) 3989-3992.
[40] S. Kantevari, R. Bantu, L.J. Nagarapu, J. Mol. Catal. A: Chem. 269 (2007) 53-57.
[41] Z.H. Zhang, Y.H. Liu, Catal. Commun. 9 (2008) 1715-1719.
[42] M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, Catal. Commun. 9 (2008) 939-942.