Abstract
A novel and efficient procedure for the synthesis of 1,8-dioxo-octahydro-xanthenes through one-pot condensation of 5,5- dimethyl-1,3-cyclohexadione with aryl aldehydes in the presence of selectfluor™ [1-(chloromethyl)-4-fluoro-1,4- diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate) as catalyst under solvent free conditions was applied. It demonstrated several advantages such as good yields of products, simple operation, convenient separation, and inexpensive catalyst.
Similar content being viewed by others
References
A. Gil, L.M. Gandia, M.A. Vicente, Cata. Rev. 42 (2002) 145.
R.S. Verma, Tetrahedron 58 (2002) 1235.
J.P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacoix, Eur. J. Med. Chem. 13 (1981) 67.
R.M. Ion, Progr. Catal. 2 (1997) 55
R.M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochim. Pol. 45 (1998) 833.
G. Saint-Ruf, A. De, H.T. Hieu, Bull. Chim. Ther. 7 (1972) 83
G. Saint-Ruf, H.T. Hieu, J.P. Poupelin, Naturwissenschaften 62 (1975) 584.
C.R. Reddy, B. Vijayakumar, P. Iycngar, G. Nagendrapp, B.S.J. Prakash, J. Mol. Catal. A 223 (2004) 117.
O. Sirkecioglu, N. Tulinli, A. Akar, J. Chem. Res. Synop. (1995) 502.
A. Bekaert, J. Andrieux, M. Plat, Tetrahedron Lett. 23 (1992) 2805
R.J. Sarma, J.B. Baruah, Dyes Pigments, 64 (2005) 91
P.S. Kumar, B.S. Kumar, B. Rajitha, P.N. Ready, N. Sreeenivasulu, Y.T. Ready, Arkivoc, xii (2006) 46
A.R. Khosropour, M.M. Khodaei, H. Moghannian, Synlett, (2005) 995
B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B. Vital Rao, J. Mol. Catal. A. Chem. 255 (2006) 74
B. Rajitha, B.S. Kumar, Y.T. Reddy, P.N. Reddy, N. Sreeenivasulu, Tetrahedron Lett. 46 (2005) 8691.
D.W. Knight, C.F. Yaho, Tetrahedron Lett. 47 (2006) 8827.
A. Jha, J. Beal, Tetrahedron Lett. 45 (2004) 8999.
K. Ota, T. Kito, Bull. Chem. Soc. Jpn. 49 (1978) 1167.
D. Shi, Y. Wang, Z. Lu, G. Dai, Synth. Commun. 30 (2000) 713.
T.S. Jin, J. S. Zhang, J.C. Xiao, A.Q. Wang, T.S. Li, Synlett. 5 (2004) 866.
E.C. Horning, M.G. Horning, J. Org. Chem. 11 (1946) 95.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Poor Heravi, M.R. Selectfluor™ promoted synthesis of 9-aryl-1,8-dioxooctahydroxanthane derivatives under solvent-free conditions. JICS 6, 483–488 (2009). https://doi.org/10.1007/BF03246525
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03246525