Home Articles List Article Information
Journal of the Iranian Chemical Research
Journal Archive
Volume Volume 5 (2012)
Volume Volume 4 (2011)
Volume Volume 3 (2010)
Volume Volume 2 (2009)
Volume Volume 1 (2008)
Mahdavinia, G. (2008). Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives using NBS as an efficient and almost neutral catalyst in aqueous media. Journal of the Iranian Chemical Research, 1(1), 11-17.
Gholam Hossein Mahdavinia. "Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives using NBS as an efficient and almost neutral catalyst in aqueous media". Journal of the Iranian Chemical Research, 1, 1, 2008, 11-17.
Mahdavinia, G. (2008). 'Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives using NBS as an efficient and almost neutral catalyst in aqueous media', Journal of the Iranian Chemical Research, 1(1), pp. 11-17.
Mahdavinia, G. Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives using NBS as an efficient and almost neutral catalyst in aqueous media. Journal of the Iranian Chemical Research, 2008; 1(1): 11-17.

Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives using NBS as an efficient and almost neutral catalyst in aqueous media

Article 2, Volume 1, Issue 1, Autumn 2008, Page 11-17  XML PDF (84 K)
Author
Gholam Hossein Mahdavinia
Chemistry Department, Islamic Azad University, Marvdasht Branch, Marvdasht, Iran
Abstract
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.
Keywords
One-pot; NBS; 1; 8-dioxo-octahydroxanthene; Organocatalyst; Aqueous media
References
[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.

 

Statistics
Article View: 727
PDF Download: 286