Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives using NBS as an efficient and almost neutral catalyst in aqueous media
الموضوعات : Journal of the Iranian Chemical Research
1 - Chemistry Department, Islamic Azad University, Marvdasht Branch, Marvdasht, Iran
الکلمات المفتاحية: 1, One-pot, NBS, 8-dioxo-octahydroxanthene, Organocatalyst, Aqueous media,
ملخص المقالة :
An efficient one-pot condensation for the synthesis of 1,8-dioxo-octahydroxanthene is achieved through a condensation of aryl aldehydes and 5,5-dimethyl-1,3-cyclohexandione in the presence of NBS. This method enjoys several advantages such as low cost, simple work up procedure and safe reaction condition. In addition, water was chosen as a green solvent.
[1] R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes, G.J. Thomas, Chem. Abstr. 126 (1997) p212377y, PCT Int. Appl. WO 9706178, (1997).
[2] T. Hideo, Chem. Abstr. 95 (1981) 80922b, Jpn. Tokkyo Koho JP 56005480, (1981).
[3] J.P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem. 13 (1978) 67.
[4] A. Banerjee, A.K. Mukherjee, Stain Technol. 56 (1981) 83.
[5] O. Sirkeeioglu, N. Talinli, A. Akar, J. Chem. Res. (S) (1995) 502.
[6] C.G. Knight, T. Stephens, Biochem. J. 258 (1989) 683.
[7] (a) S. Hatakeyma, N. Ochi, H. Numata, S. Takano. J. Chem. Soc. Chem. Commun. (1988) 1202, and refs. Cited therein. (b) G.M. Cingolant, M. Pigini, J. Med. Chem. 12 (1988) 531.
[8] C.N. O’Callaghan, T.B.H. McMurry, J. Chem. Res. Synop. (1995) 214; J. Chem. Res. Miniprint (1995) 1448.
[9] J. Kuthan, P. Sebek, S. Bohm, Advances in Heterocyclic Chemistry. Vol. 62. Academic Press, Inc., New York. 1995, p. 19.
[10] (a) T.S. Jin, J.S. Zhang, J.C. Xio, A.Q. Wang, T.S. Li, Synlett (2004) 866. (b) T.S. Jin, J.S. Zhang, A.Q. Wang, T.S. Li, Ultrason. Sonochem. 13 (2006) 220.
[11] A. R. Khosropour, M.M. Khodaei, H. Moghannian, Synlett (2005) 955.
[12] B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth, L. Nagarapu, Catal. Commun. 8 (2007) 535.
[13] X. Fan, X. Hu, X. Zhang, J. Wang, Can. J. Chem. 83 (2005) 16.
[14] B. Das, P. Thirupathi, I. Mahender, V.S. Reddy, Y.K. Rao, J. Mol. Catal. A: Chem. 247 (2006) 233.
[15] A. John, J.P. Yadav, S. Palaniappan, J. Mol. Catal. A: Chem. 248 (2006) 121.
[16] S. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Catal. A: Chem. 269 (2007) 53.
[17] (a) D.C. Rideout, R. Breslow, J. Am. Chem. Soc. 102 (1980) 7817. (b) R. Breslow, U. Maitra, D. Rideout, Tetrahedron Lett. 24 (1983) 1901. (c) T.A. Eggelte, H. De Koning, H.O. Huisman, Tetrahedron 29 (1973) 2491.
[18] (a) J.J. Gajewski, J. Jurayj, D.R. Kimbrough, M.E. Grande, B. Ganem, B.K. Carpenter, J. Am. Chem. Soc. 109 (1987) 1170. (b) E. Brandes, P.A. Grieco, J.J. Gajewski, J. Org. Chem. 54 (1989) 515. (c) P.A. Grieco, E.B Brandes, S. McCann, J.D. Clark, J. Org. Chem. 54 (1989) 5849. (d) D.L. Severance, W.L. Jorgensen, J. Am. Chem. Soc. 114 (1992) 10966. (e) J.Gao, J. Am. Chem. Soc. 116 (1994) 1563. (f) J.J. Gajewski, N.L. Brichford, J. Am. Chem. Soc. 116 (1994) 3165.
[19] (a) A. Lubineau, J. Org. Chem. 51 (1986) 2143. (b) A. Lubineau, E. Meyer, Tetrahedron 44 (1988) 6065.
[20] (a) E.T. Kool, R. Breslow, J. Am. Chem. Soc. 110 (1988) 1596. (b) R. Breslow, Acc. Chem. Res. 24 (1991) 159.
[21] (a) C.J. Li, Chem. Rev. 93 (1993) 2023. (b) P.A. Grieco, Organic Synthesis in Water, Blacky: London, 1998. (c) C.J. Li, T.H. Chan, Organic Reactions in Aqueous Media, Wiley: New York, 1997.
[22] P.I. Dalko, L. Moisan, Angew. Chem., Int. Ed. 43 (2004) 5138.
[23] (a) K. Surendra, N.S. Krishnaveni, V.P. Kumar, R. Sridhar, K.R. Rao, Tetrahedron Lett. 46 (2005) 4581; (b) B. Karimi, H. Hazarkhani, J. Maleki, Synthesis (2005) 279; (c) S.K. Talluri, A. Sudalai, Org. Lett. 7 (2005) 855; (d) N.S. Krishnaveni, K. Surendra, K.R. Rao, Adv. Synth. Catal. 346 (2004) 346; (e) R. Rajagopal, D.V. Jarikote, R.J. Lahoti, D. Thomas, K.V. Srinivasan, Tetrahedron Lett. 44 (2003) 1815; (f) A. Podgorsek, S. Stavber, M. Zupan, J. Iskra, Tetrahedron Lett. 47 (2006) 1097; (g) I. Pravst, M. Zupan, S. Stavbre, Tetrahedron Lett. 47 (2006) 4707; (h) J. Wu, W. Sun, X. Sun, H.-G. Xia, Green Chem. 8 (2006) 365; (i) C.-W. Kuo, S.V. More, C.-F. Yao, Tetrahedron Lett. 47 (2006) 8523.
[24] (a) M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun. 8 (2007) 1595; (b) M.A. Bigdeli, S. Jafari, G.H. Mahdavinia, H. Hazarkhani, Catal. Commun. 8 (2007) 1641; (c) M.A. Bigdeli, G.H. Mahdavinia, S. Jafari, J. Chem. Res. (2007) 26. (d) M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, J. Mol. Catal. A: Chem. 275 (2007) 25; (e) M.A. Bigdeli, G.H. Mahdavinia, S. Jafari, H. Hazarkhani, Catal. Commun. 8 (2007) 2228.
[25] E.C. Horning, M.G. Horing, J. Org. Chem. 11 (1946) 95.
