One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions

doi:10.1007/s40242-014-3520-5

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (4): 632-638.doi: 10.1007/s40242-014-3520-5

One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions

ZONG Chenglong, ZENG Runsheng, ZOU Jianping

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China

出版日期:2014-08-01 发布日期:2014-04-14
通讯作者: ZENG Runsheng E-mail:Zengrunsheng@suda.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(Nos.20772088, 21172163) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions

ZONG Chenglong, ZENG Runsheng, ZOU Jianping

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China

Online:2014-08-01 Published:2014-04-14
Contact: ZENG Runsheng E-mail:Zengrunsheng@suda.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.20772088, 21172163) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

摘要/Abstract

摘要：

A direct and efficient approach to synthesize imidazo[1,2-a]pyridines through three-component one-pot reaction of 2-aminopyridine, aldehyde and terminal alkyne catalyzed by Cu-nanoparticles under solvent-free conditions has been developed. This method provides a rapid access to substituted imidazo[1,2-a]pyridines with good yields(up to 85%).

关键词: Copper nanoparticle, Three-component reaction, Solvent-free condition, 2-Aminopyridine, Aldehyde, Alkyne

Abstract:

Key words: Copper nanoparticle, Three-component reaction, Solvent-free condition, 2-Aminopyridine, Aldehyde, Alkyne

ZONG Chenglong, ZENG Runsheng, ZOU Jianping. One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions[J]. 高等学校化学研究, 2014, 30(4): 632-638.

ZONG Chenglong, ZENG Runsheng, ZOU Jianping. One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions[J]. Chemical Research in Chinese Universities, 2014, 30(4): 632-638.

参考文献

[1] Al-Tel T. H., Semreen M. H., Al-Qawasmeh R. A., Schmidt M. F., El-Awadi R., Ardah M., Zaarour R., Rao S. N., El-Agnaf O., J. Med. Chem., 2011, 54, 8373
[2] Dahan-Farkas N., Langley C., Rousseau A. L., Yadav D. B., Davids H., de Koning C. B., Eur. J. Med. Chem., 2011, 46, 4573
[3] Kaminski J. J., Doweyko A. M., J. Med. Chem., 1997, 40, 427
[4] Kaminski J. J., Hilbert J. M., Pramanik B. N., Solomon D. M., Conn D. J., Rizvi R. K., Elliott A. J., Guzik H., Lovey R. G., J. Med. Chem., 1987, 30, 2031
[5] Lhassani M., Chavignon O., Chezal J. M., Teulade J. C., Chapat J. P., Snoeck R., Andrei G., Balzarini J., de Clercq E., Gueiffier A., Eur. J. Med. Chem., 1999, 34, 271
[6] Terao Y., Suzuki H., Yoshikawa M., Yashiro H., Takekawa S., Fujitani Y., Okada K., Inoue Y., Yamamoto Y., Nakagawa H., Yao S., Kawamoto T., Uchikawa O., Bioorg. Med. Chem. Lett., 2012, 22, 7326
[7] Ulloora S., Shabaraya R., Aamir S., Adhikari A. V., Bioorg. Med. Chem. Lett., 2013, 23, 1502
[8] Moraski G. C., Markley L. D., Cramer J., Hipskind P. A., Boshoff H., Bailey M. A., Alling T., Ollinger J., Parish T., Miller M. J., ACS Med. Chem. Lett., 2013, 4, 675
[9] Meirer K., Rödl C. B., Wisniewska J. M., George S., Häfner A. K., Buscató E., Klingler F. M., Hahn S., Berressem D., Wittmann S. K., Steinhilber D., Hofmann B., Proschak E., J. Med. Chem., 2013, 56, 1777
[10] Enguehard-Gueiffier C., Musiu S., Henry N., Véron J. B., Mavel S., Neyts J., Leyssen P., Paeshuyse J., Gueiffier A., Eur. J. Med. Chem., 2013, 64, 448
[11] Swainston H. T., Keating G. M, CNS Drugs, 2005, 19, 65
[12] Jain A. N., J. Med. Chem., 2004, 47, 947
[13] Enguehard-Gueiffier C., Gueiffier A., Mini-Rev. Med. Chem., 2007, 7, 888
[14] Gueiffier A., Mavel S., Lhassani M., Elhakmaoui A., Snoeck R., Andrei G., Chavignon O., Teulade J. C., Witvrouw M., Balzarini J., de Clercq E., Chapat J. P., J. Med. Chem., 1998, 41, 5108
[15] Denora N., Laquintana V., Pisu M. G., Dore R., Murru L., Latrofa A., Trapani G., Sanna E., J. Med. Chem., 2008, 51, 6876
[16] Adib M., Shebani E., Zhu L. G., Mirzaei P., Tetrahedron Lett., 2008, 49, 5108
[17] Yadav J. S., Reddy B. V. S., Rao Y. G., Srinivas M., Narsaiah A. V., Tetrahedron Lett., 2007, 48, 7717
[18] Katritzky A. R., Xu Y. J., Tu H., J. Org. Chem., 2003, 68, 4935
[19] Bienaymé H., Bouzid K., Angew. Chem. Int. Ed., 1998, 37, 2234
[20] Shaabani A., Soleimani E., Maleki A., Tetrahedron Lett., 2006, 47, 3031
[21] Adib M., Mahdavi M., Noghani M. A., Mirxaei P., Tetrahedron Lett., 2007, 48, 7263
[22] Reddy B. V. S., Reddy P. S., Reddy Y. J., Yadav J. S., Tetrahedron Lett., 2011, 52, 5789
[23] Alexandra B. L., Thiago M. A., Alexandre M., Jean J. B., Tetrahedron Lett., 2012, 53, 2583
[24] Thiruvengadam P., Kyungho P., Manian R. K., Jung H. M., Lee S., Eur. J. Org. Chem., 2012, 5038
[25] Sankar K. G., Ajay L. C., Garima P., J. Org. Chem., 2012, 77, 4438
[26] Chernyak N., Gevorgyan V., Angew. Chem. Int. Ed., 2010, 49, 2743
[27] Liu P., Fang L. S., Lei X. S., Lin G. Q., Tetrahedron Lett., 2010, 51, 4605
[28] Liu P., Deng C. L., Lei X. S., Lin G. Q., Eur. J. Org. Chem., 2011, 7308
[29] Adib M., Sheikhi E., Rezaei N., Tetrahedron Lett., 2011, 52, 3191
[30] Guntreddi T., Allam B. K., Singh K. N., Synlett., 2012, 23, 2635
[31] Bharate J. B., Guru S. K., Jain S. K., Meena S. S., Parvinder P., Bhushan S., Singh B., Bharate S. B., Vishwakarma R. A., RSC Advances 2013, 3, 20869
[32] Yan N., Xiao C., Kou Y., Coord. Chem. Rev., 2010, 254, 1179
[33] Polshettiwar V., Varma R. S., Green Chem., 2010, 12, 743
[34] Alonso F., Riente P., Yus M., Acc. Chem. Res., 2011, 44, 379
[35] Bhadra S., Saha A., Ranu B. C., Green Chem., 2008, 10, 1224
[36] Kidwai M., Mishra N. K., Bansal V., Kumar A., Mozumdar S., Tetrahedron Lett., 2009, 50, 1355
[37] Alonso F., Moglie Y., Radivoy G., Yus M., Tetrahedron Lett., 2009, 50, 2358
[38] Alonso F., Moglie Y., Radivoy G., Yus M., Eur. J. Org. Chem., 2010, 1875
[39] Tanaka K., Toda F., Chem. Rev., 2000, 100, 1025
[40] Martins M. A. P., Frizzo C. P., Moreira D. N., Buriol L., Machado P., Chem. Rev., 2009, 109, 4140
[41] Jin J. N., Zhang J. M., Liu F. R., Shang W. L., Xin Y., Zhu S. Z., Chin. J. Chem., 2010, 28, 1217
[42] Yan W. J., Wang R., Xu Z. Q., Xu J. K., Li L., Shen Z. Q., Zhou Y. F., J. Mol. Catal. A: Chem., 2006, 255, 81
[43] Kidwai M., Bansal V., Kumar A., Mozumdar S., Green Chem., 2007, 9, 742
[44] Sreedhar B., Kumar A. S., Reddy P. S., Tetrahedron Lett., 2010, 51, 1891

One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions

One-pot Copper Nanoparticle-catalyzed Synthesis of Imidazo[1,2-a]pyridines Under Solvent-free Conditions

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