Facile synthesis of unsymmetrical N-aryl-2,2-di(1H-indol-3-yl) acetamide derivatives

Yan Zhou , Renjun Li , Xiaolong Wang , Ling He , Mei Guan , Yong Wu

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (6) : 959 -966.

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Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (6) : 959 -966. DOI: 10.1007/s40242-016-6233-0
Article

Facile synthesis of unsymmetrical N-aryl-2,2-di(1H-indol-3-yl) acetamide derivatives

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Abstract

A facile and highly efficient method has been developed for the synthesis of unsymmetrical N-aryl-2,2-di(1H-indol-3-yl)acetamide derivatives by regioselective Friedel-Crafts alkylation of the N-aryl-2-hydroxy-2-(1H-indol-3-yl) acetamide derivatives with various indoles catalyzed by 2 mol/L H2SO4 at room temperature in a short reaction time, the yield was up to 94%.

Keywords

N-Aryl-2,2-di(1H-indol-3-yl)acetamide derivative / Indole / Unsymmetry / Friedel-Crafts alkylation / Brønsted acid

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Yan Zhou, Renjun Li, Xiaolong Wang, Ling He, Mei Guan, Yong Wu. Facile synthesis of unsymmetrical N-aryl-2,2-di(1H-indol-3-yl) acetamide derivatives. Chemical Research in Chinese Universities, 2016, 32(6): 959-966 DOI:10.1007/s40242-016-6233-0

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References

[1]

Goldberg A. A., Titorenko V. I., Beach A., Abdelbaqi K., Safe S., Sanderson J. T. Invest. New Drug, 2014, 32: 25.

[2]

Saton A., Nishina Y. Cell-death Inhibitor, and Production Method Therefor, 2014.

[3]

Tomomi N. Y., Masashi T., Hiroshi A., Yuichi H. Chem. Pharm. Bull., 2009, 57: 536.

[4]

Cho S. D., Yoon K., Chintharlapalli S., Abdelrahim M., Lei P., Hamilton S., Khan S., Ramaiah S. K., Safe S. Cancer Res., 2007, 67(2): 674.

[5]

Miranda B. R. D., Miller J. A., Hansen R. J., Lunghofer P. J., Safe S., Gustafson D. L., Colagiovanni D., Tjalkens R. B. J. Pharmacol. Exp. Ther., 2013, 345: 125.

[6]

Mjalli A. M. M., Shahbaz K. G. J. Bis-heteroaryl Alkanes as Thera-peutic Agents, 2003.

[7]

Contractor R., Samudio I. J., Estrov Z., Harris D., McCubrey J. A., Safe S. H., Andreeff M., Konopleva M. Cancer Res., 2005, 65: 2890.

[8]

Wang Y., Tang X. X., Shao Z. Z., Ren J. W., Liu D., Proksch P., Lin W. H. J. Antibiot., 2014, 67: 395.

[9]

Paira P., Hazra A., Kumar S., Paira R., Sahu K. B., Naskar S., saha P., Mondal S., Maity A., Banerjee S., Mondal N. B. Bioorg. Med. Chem. Lett., 2009, 19: 4786.

[10]

Yoo M., Choi S. U., Choi K. Y., Yon G. H., Chae J. C., Kim D., Zyl-stra G. J., Kim E. Biochem. Biophys. Res. Commun., 2008, 376: 96.

[11]

He X. M., Hu S. Z., Liu K., Guo Y., Xu J., Shao S. J. Org. Lett., 2006, 8: 333.

[12]

Lee G. W., Kim N. K., Jeong K. S. Org. Lett., 2010, 12: 2634.

[13]

Zhang J. M., Xu R. P., Tian Y., Zhou J. H. Chem. Res. Chinese Uni-versities, 2009, 25(6): 941.

[14]

Zeng X. F., Ji S. J., Wang S. Y. Tetrahedron, 2005, 61: 10235.

[15]

Nikpassand M., Mamaghani M., Tabatabaeian K., Samimi H. A. Synth. Commun., 2010, 40: 3552.

[16]

Lin H., Zang Y., Sun X. W., Lin G. Q. Chin. J. Chem., 2012, 30: 2309.

[17]

Jadhav S. D., Singh A. J. Org. Chem., 2016, 81(2): 522.

[18]

Ma S. M., Yu S. C. J. Org. Lett., 2005, 7(22): 5063.

[19]

Moghadam K. R., Kiasaraie M. S., Amlashi H. T. Tetrahedron, 2010, 66: 2316.

[20]

Pathak T. P., Osiak J. G., Vaden R. M., Welm B. E., Sigman M. S. Tetrahedron, 2012, 68: 5203.

[21]

Wu K. K., Wu P., Wang L. D., Chen J. P., Sun C. L., Yu Z. K. Adv. Synth. Catal., 2014, 356: 3871.

[22]

Chakrabarty M., Basak R., Ghosha N., Harigaya Y. Tetrahedron, 2004, 60: 1941.

[23]

Srivastava A., Yadav A., Samanta S. Tetrahedron Lett., 2015, 56: 6003.

[24]

Li M. H., Taheri A., Liu M., Sun S. H., Gua Y. L. Adv. Synth. Catal., 2014, 356: 537.

[25]

Chakrabarty M., Basak R., Ghosh N. Tetrahedron Lett., 2001, 42: 3913.

[26]

Wen H., Wang L., Xu L. B., Hao Z. H., Shao C. L., Wang C. Y., Xiao J. Adv. Synth. Catal., 2015, 357: 4023.

[27]

Xiao J., Wen H., Wang L., Xu L. B., Hao Z. H., Shao C. L., Wang C. Y. Green Chem., 2016, 18: 1032.

[28]

Lv G. H., Cheng X., Zheng Y., Li W. J., HAI L., Wu Y. Chem. Res. Chinese Universities, 2016, 32(2): 212.

[29]

Zhan Z., Li R. J., Zheng Y., Zhou Y., Hai L., Wu Y. Synlett., 2015, 26: 2261.

[30]

Zheng Y., Li R. J., Zhan Z., Hai L., Wu Y. Chin. Chem. Lett., 2016, 27: 41.

[31]

Finefield J. M., Williams R. M. J. Org. Chem., 2010, 75: 2785.

[32]

Akao A., Nonoyama N., Mase T., Yasuda N. Org. Process. Res. Dev., 2006, 10: 1178.

[33]

Choy P. Y., Lau C. P., Kwong F. Y. J. Org. Chem., 2011, 76: 80.

[34]

Ontoria J. M., Marco S. D., Conte I., Francesco M. E. D., Gardelli C., Koch U., Matassa V. G., Poma M., Steinkühler C., Volpari C., Harper S. J. Med. Chem., 2004, 47: 6443.

[35]

Kreutter K. D., Lu T. B., Lee L., Giardino E. C., Patel S., Huang H., Xu G. Z., Fitzgerald M., Haertlein B. J., Mohan V., Crysler C., Ei-sennagel S., Dasgupta M., McMillan M., Spurlino J. C., Huebert N. D., Maryanoff B. E., Tomczuk B. E., Damiano B. P., Player M. R. Bioorg. Med. Chem. Lett., 2008, 18: 2865.

[36]

Sparks S. M., Chow C., Zhu P.L., Shea K. J. J. Org. Chem., 2004, 69: 302.

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