Efficient one-pot synthesis of 12-Aryl-8, 9, 10, 12-tetrahydrobenzo[a]xanthen-11-ones under solvent-free conditions

Abstract

Multi-component condensation of 2-naphthol, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds catalyzed by ionic liquid [NSPTEA][HSO₄] was accomplished for the synthesis of a series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones under solvent-free conditions. High yields, ease recovery, short reaction time and reusability of catalyst are significant advantages. ZrOCl₂·8H₂O was also found to act as an effective catalyst towards this transformation.

Keywords

Aldehyde / Ionic liquid / ZrOCl₂·8H₂O / Multi-component reaction / Solvent-free condition

References

[1] Anastas P. T., Warner J. C. Green Chemistry: Theory and Practice, 1998, Oxford: Oxford University Press.

[2] Tejedor D., Garcia-Tellado F. Chem. Soc. Rev., 2007, 36: 484.

[3] Thompson L. A. Curr. Opin. Chem. Biol., 2000, 4: 324.

[4] Lambert R.W., Martin J. A., Merrett J. H., Parkes K. E. B., Thomas G. J., Pyrimidine Nucleosides, WO 9706178, 1997

[5] Poupelin J. P., Saint-Ruf G., Foussard-Blanpin O., Narcisse G., Uchida-Ernouf G., Lacroix R. Eur.. J. Med. Chem., 1978, 13: 67.

[6] Hideo T., Teruomi J., 1-Benzopyrano 2,3-Bxanthene Derivative and Its Preparation, Jpn. 56005480, 1981

[7] Buu-Hoi N. P., Saint-Ruf G., De A., Hieu H. T. Bull. Chim. Ther., 1972, 7: 83.

[8] Ion R. M., Planner A., Wiktorowicz K., Frackowiak D. Acta Biochim. Pol., 1998, 45: 833.

[9] Menchen S. M., Benson S. C., Lam J. Y. L., Zhen W. G., Sun D. Q., Rosenblum B. B., Khan S. H., Taing M., Sulfonated Diarylrhodamine Dyes, US 6583168, 2003

[10] Ahmad M., King T. A., Ko D.-K., Cha B. H., Lee J. J. Phys. D: Appl. Phys., 2002, 35: 1473.

[11] Knight C. G., Stephens T. Biochem. J., 1989, 258: 683.

[12] Mashraqui S. H., Patil M. B., Mistry H. D., Ghadigaonkar S., Meetsma A. Chem. Lett., 2004, 33: 1058.

[13] Das B., Laxminarayana K., Krishnaiah M., Srinivas Y., Synlett., 2007, 3107

[14] Li J. J., Tang W. Y., Lu L. M., Su W. K. Tetrahedron Lett., 2008, 49: 7117.

[15] Gao S., Tsai C. H., Yao C. F., Synlett., 2009, 949

[16] Wang R. Z., Zhang L. F., Cui Z. S. Synth. Commun., 2009, 39: 2101.

[17] Nandi G. C., Samai S., Kumar R., Singh M. S. Tetrahedron, 2009, 65: 7129.

[18] Khurana J. M., Magoo D. Tetrahedron Lett., 2009, 50: 4777.

[19] Wasserscheid P., Welton T. Ionic Liquid in Synthesis, 2007, Weinheim: Wiley-VCH.

[20] Litschauer M., Neouze M. A. J. Mater. Chem., 2008, 18: 640.

[21] Lee S. G., Chem. Commun., 2006, 1049

[22] Wang Z., Zhang Q., Kuehner D., Ivaska A., Niu L. Green Chem., 2008, 10: 907.

[23] Jiang Y. Y., Wang G. N., Zhou Z., Wu Y. T., Geng J., Zhang. Z. B., Chem. Commun., 2008, 505

[24] Zhao G., Jiang T., Gao H., Han B., Huang J., Sun D. Green Chem., 2004, 6: 57.

[25] Li X., Geng W., Zhou J., Luo W., Wang F., Wang L., Tsang S. C. New J. Chem., 2007, 31: 2088.

[26] Holbrey J. D., Turner M. B., Reichert W. M., Rogers R. D. Green Chem., 2003, 5: 731.

[27] Lee S. G., Chem. Commun., 2006, 1049

[28] Davis J. H. Jr., Chem. Lett., 2004, 33: 1072.

[29] Cole A. C., Jensen J. L., Ntai I., Tran K. L. T., Weaver K. J., Forbes D. C., Davis J. H. Jr., J. Am. Chem. Soc., 2002, 124: 5962.

[30] Zhao G. Y., Jiang T., Gao H. X., Han B. X., Huang J., Sun D. H. Green. Chem., 2004, 6: 75.

[31] Xu J. M., Liu B. K., Wu W. B., Qian C., Wu Q., Lin X. F. J. Org. Chem., 2006, 71: 3991.

[32] Ranu B. C., Banerjee S. Org. Lett., 2005, 7: 3049.

[33] Suman S., Trissa J., Halligudi S. B. J. Mol. Catal. A: Chem., 2006, 244: 179.

[34] Wu W. Z., Han B. X., Gao H. X., Liu Z., Jiang M., Huang T. Angew. Chem. Int. Ed., 2004, 43: 2415.

[35] Xu D. Q., Wu J., Luo S. P., Zhang J., Wu J. Y., Du X. H., Xu Z. Y. Green Chem., 2009, 11: 1239.

[36] Jiang F., Lin Y. J., Duan H. F., Li Z. H., Cao J. G., Liang D. P. Chem. Res. Chinese Universities, 2010, 26(3): 384.

[37] Firouzabadi H., Iranpoor N., Jafarpour M., Ghaderi A. J. Mol. Catal. A: Chem., 2006, 252: 150.

[38] Hashemi M. M., Eftekhari-Sis B., Abdollahifar A., Khalili B. Tetrahedron, 2006, 62: 672.

[39] Ghosh R., Maiti S., Chakraborty A., Chakraborty S., Mukherjee A. K. Tetrahedron, 2006, 62: 4059.

[40] Moghaddam F. M., Ismaili H., Bardajee G. R. Heteroatom Chem., 2006, 17: 136.

[41] Nakayama M., Sato A., Ishihara K., Yamamoto H. Adv. Synth. Catal., 2004, 346: 1275.

[42] Mantri K., Komura K., Sugi Y., Synthesis, 2005, 1939

[43] Ghosh R., Maiti S., Chakraborty A. Tetrahedron Lett., 2005, 46: 147.

[44] Yakaiah T. G., Reddy V.B., Lingaiah P. V., Rao P. S., Narsaiah B. Indian J. Chem., 2005, 44B: 1301.

[45] Firouzabadi H., Iranpoor N., Jafarpour M., Ghaderi A. J. Mol. Catal. A: Chem., 2006, 253: 249.

[46] Rodriguez-Dominguez J. C., Kirsch G., Synthesis, 2006, 1895

[47] Nagawade R. R., Shinde D. B. Russ. J. Org. Chem., 2006, 42: 465.

[48] Shirini F., Zolfigol M. A., Mllarazi E. Synth. Commun., 2006, 36: 2307.

[49] Mohammadpoor-Baltork I., Khosropour A. R., Hojati S. F. Catal. Commun., 2007, 8: 200.

[50] Wu M. C., Duan H. F., Cao J. G., Liang D. P., Jiang F., Gao H., Jia X. D., Lin Y. J. Chem. Res. Chinese Universities, 2011, 27(6): 973.

[51] Jia X. D., Duan H. F., Lin Y. J., Cao J. G., Liang D. P., Luo X. Y., Jiang F., Gao H., Wu M. C. Chem. Res. Chinese Universities, 2010, 26(3): 394.

[52] Gao H., Jia X. D., Duan H. F., Lin Y. J., Cao J. G., Liang D. P., Wu M. C. Chem. Res. Chinese Universities, 2011, 27(5): 792.

[53] Khodaei M. M., Khosropour A. R., Moghanian H., Synlett., 2006, 916

[54] Nagarapu L., Baseeruddin M., Apuri S., Kantevari S. Catal. Commun., 2007, 8: 1729.