Chinese Journal of Organic Chemistry >
Cyanuric Chloride-Promoted Synthesis of Imidazo[1,2-a]pyridines
Received date: 2013-07-03
Revised date: 2013-09-23
Online published: 2013-10-11
Cyanuric chloride-promoted synthesis of imidazo[1,2-a]pyridine derivatives was realized in high yields by the reaction of 2-aminopyridines, aldehydes and isonitriles in CH3CN at room temperature. All products were characterized by 1H NMR, 13C NMR and elemental analysis.
Yin Zhikui , Tian Shuanbao . Cyanuric Chloride-Promoted Synthesis of Imidazo[1,2-a]pyridines[J]. Chinese Journal of Organic Chemistry, 2014 , 34(2) : 387 -391 . DOI: 10.6023/cjoc201307004
[1] (a) Sasaki, A.; Kitamura, K.; Alcalde, R. E.; Tanaka, T.; Suzuki, A.; Etoh, Y.; Matsumura, T. Int. J. Caner 1998, 77, 279.
(b) Jaramillo, C.; de Diego, J. E.; Hamdouchi, C.; Collins, E.; Keyser, H.; Sánchez-Martínez, C.; del Prado, M.; Norman, B.; Brooks, H. B.; Watkins, S. A.; Spencer, C. D.; Dempsey, J. A.; Anderson, B. D.; Campbell, R. M.; Leggett, T.; Patel, B.; Schultz, R. M.; Espinosa, J.; Vieth, M.; Zhang, F.; Timm, D. E. Bioorg. Med. Chem. Lett. 2004, 20, 6095.
(c) Hayakawa, M.; Kaizawa, H.; Kawaguchi, K.; Ishikawa, N.; Koizumi, T.; Ohishi, T.; Yamano, M.; Okada, M.; Ohta, M.; Tsukamoto, S.; Raynaud, F. I.; Waterfield, M. D.; Parker, P.; Workman, P. Bioorg. Med. Chem. 2007, 15, 403.
[2] (a) Gudmundsson, K. S.; Williams, J. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2003, 46, 1449.
(b) Hamdouchi, C.; de Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.
(c) Lhassani, M.; Chavignon, O.; Chezal, J. M.; Teulade, J. C.; Chapat, J. P.; Snoeck, R.; Andrei, G.; Balzarini, J.; Clercq, E.; Gueier, A. Eur. J. Med. Chem. 1999, 34, 271.
[3] Starrett, J. E.; Montzka, T. A.; Crosswell, A. R.; Cavanagh, R. L. J. Med. Chem. 1989, 32, 2204.
[4] Kercher, T.; Rao, C.; Bencsik, J. R.; Josey, J. A. J. Comb. Chem. 2007, 9, 1177.
[5] Ismail, M. A.; Brun, R.; Wenzler, T.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. J. Med. Chem. 2004, 47, 3658.
[6] (a) Zhou, J. L.; Liu, J. C.; Chen, Q. Y. Chin. J. Org. Chem. 2009, 29, 1708 (in Chinese).
(周建良, 刘建超, 陈启元, 有机化学, 2009, 29, 1708.)
(b) Zhang, R. Ph.D. Dissertation, Zhejiang University, Hangzhou, 2007 (in Chinese).
(张睿, 博士论文, 浙江大学, 杭州, 2007.)
(c) Li, Z. R. M.S. Thesis, Qingdao University of Science and Technology, Qingdao, 2009 (in Chinese).
(李兆瑞, 硕士论文, 青岛科技大学, 杭州, 2009.)
[7] (a) Chen, J. J.; Golebiowski, A.; McClenaghan, J.; Klopfenstein, S. R.; West, L. Tetrahedron Lett. 2001, 2269.
(b) Lyon, M. A.; Kercher, T. S. Org. Lett. 2004, 6, 4989.
(c) Blackburn, C.; Guan, B. Tetrahedron Lett. 2000, 41, 1495.
(d) Rostamnia, S.; Lamei, K.; Mohammadquli, M.; Sheykhan, M.; Heydari, A. Tetrahedron Lett. 2012, 53, 5257.
(e) Bienayme, H.; Bouzid, K. Angew. Chem., Int. Ed. 1998, 37, 2234.
(f) Shaabani, A.; Soleimani, E.; Maleki, A.; Moghimi-Rad, J. Synth. Commun. 2008, 38, 1090.
(g) Shaabani, A.; Maleki, A.; Rad, J.; Soleimani, E. Chem. Pharm. Bull. 2007, 55, 957.
(h) Rousseau, A. L.; Matlaba, P.; Parkinson, C. J. Tetrahedron Lett. 2007, 48, 4079.
(i) Bode, M. L.; Gravestock, D.; Moleele, S. S.; vander Westhuyzen C. W.; Pelly, S. C.; Steenkamp, P. A.; Hoppe, H. C.; Khan, T.; Nkabinde, L. A. Bioorg. Med. Chem. 2011, 19, 4227.
(j) Khan, A. T.; Basha, R. S.; Lal, M. Tetrahedron Lett. 2012, 53, 2211.
(k) Shaabani, A.; Soleimani, E.; Sarvari, A.; Rezayan, A. H.; Maleki, A. Chin. J. Chem. 2009, 27, 369.
[8] (a) Blackburn, G. B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahedron Lett. 1998, 39, 3635.
(b) Shaabani, A.; Soleimani, E.; Sarvary, A.; Rezayan, A. H.; Maleki, A. Chin. J. Chem. 2009, 27, 369.
(c) Odell, L. R.; Nilsson, M.; Gising, J.; Lagerlund, O.; Muthas, D.; Nordqvist, A.; Karlen, A.; Larhed, M. Bioorg. Med. Chem. Lett. 2009, 19, 4790.
(d) Rousseau, A. L.; Matlaba, P.; Parkinson, C. J. Tetrahedron Lett. 2007, 48, 4079.
(e) Shaabani, A.; Soleimani, E.; Maleki, A.; Moghimi-Rad, J. Synth. Commun. 2008, 38, 1090.
(f) Shukla, N. M.; Salunke, D. B.; Yoo, E.; Mutz, C. A.; Balakrishna, R.; David, S. A. Bioorg. Med. Chem. 2012, 20, 5850.
(g) Shaabani, A.; Maleki, A.; Moghimi, R. J.; Soleimani, E. Chem. Pharm. Bull. 2007, 55, 957.
[9] (a) Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 7665.
(b) Ireland, S. M.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2003, 44, 4369.
[10] Shaabani, A.; Soleimani, E.; Maleki, A. Tetrahedron Lett. 2006, 47, 3031.
[11] Yang, C. G.; Fang, L. Z.; Wu, L. Q.; Yan, F. L. Asian J. Chem. 2010, 22, 6031.
[12] Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2004, 45, 7729.
[13] Wu, L. Q.; Yang, X. J.; Wang, X.; Yan, F. L. J. Sulfur Chem. 2010, 31, 509.
[14] Bigdeli, M. A.; Heravi, M. M.; Mahdavinia, G. H. Catal. Commun. 2007, 8, 1595.
[15] Sun, P. L.; Fang, L. Z.; Wu, L. Q. J. Sulfur Chem. 2011, 32, 257.
[16] Adib, M.; Mahdavi, M.; Noghani, M. A.; Mirzaei, P. Tetrahedron Lett. 2007, 48, 7263.
[17] Adib, M.; Sheikhi, E.; Rezaei, N. Tetrahedron Lett. 2011, 52, 3191.
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