Efficient One-pot Synthesis of 12-Aryl-8, 9, 10, 12- tetrahydrobenzo[a]xanthen-11-ones Under Solvent-free Conditions

doi:10.1007/s40242-013-0001-1

摘要/Abstract

摘要：

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.

关键词: Aldehyde, Ionic liquid, ZrOCl₂·8H₂O, Multi-component reaction, Solvent-free condition

Abstract:

Key words: Aldehyde, Ionic liquid, ZrOCl₂·8H₂O, Multi-component reaction, Solvent-free condition

JIA Xu-dong, HAN Song-yang, DUAN Hai-feng, LIN Ying-jie, CAO Jun-gang, LIANG Da-peng, WU Mao-cheng. Efficient One-pot Synthesis of 12-Aryl-8, 9, 10, 12- tetrahydrobenzo[a]xanthen-11-ones Under Solvent-free Conditions[J]. 高等学校化学研究, 2013, 29(1): 82-86.

参考文献

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

[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, Wiley- VCH, Weinheim, 2007

[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