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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

K2CO3 Promoted Cascade Reaction for the Preparation of 1H-Imidazol-4- yl-1-amine Derivatives

Author(s): Wei Xu, Hao Yao, Xing Zhang, Changjiang Peng, Ling Li, Yuanyuan Zhang, Shan Qian, Lingling Yang* and Zhouyu Wang*

Volume 17, Issue 2, 2020

Page: [127 - 132] Pages: 6

DOI: 10.2174/1570178616666190226144620

Price: $65

Abstract

A K2CO3 promoted efficient one pot two-step method for the preparation of 1H-imidazol-4- yl-1-amine derivatives has been developed. A series of second amines with an imidazole group were obtained with 56%-91% yields by the K2CO3 promoted amination of acetates and nitrogen deprotection of the imidazole process.

Keywords: One pot, second amine, imidazole, nucleophilic displacement, K2CO3, amination.

Graphical Abstract
[1]
Armer, R.; Bingham, M.; Pesnot, T.; Cignoux, C. PCT Int. Appl. WO 2016051181,. 2016.
[2]
Fan, Y.L.; Jin, X.H.; Huang, Z.P.; Yu, H.F.; Zeng, Z.G.; Gao, T.; Feng, L.S. Eur. J. Med. Chem., 2018, 150, 347-365.
[3]
Guido, G.; Henri, S.; Annick, G.; Marius, H.C.; Roger, D.N. Bioorg. Med. Chem. Lett., 2012, 22, 5244-5248.
[4]
Anil, V.; Yimin, Q.; Andreas, V.; Michelle, A. B.; Junko, O.; Said, M. S.; Andrew D., H. J. Med. Chem., 1999, 42, 1333-1340.
[5]
Bureš, F.; Kulhánek, J. Tetrahedron Asymmetry, 2005, 16, 1347-1354.
[6]
Baxter, E.W.; Reitz, A.B. Org. React; Wiley, 2002, p. 1.
[7]
Birtill, J.J.; Chamberlain, M. Hall. J.; Wilson, R.; Costello, I. In: Catalysis of Organic Reactions; Herkers, F.E., Ed.; Dekker: New York, USA, 1998; pp. 255-271.
[8]
Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E.N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, USA, 2004, 1, pp. 199-222.
[9]
Nugent, T.C.; El-Shazly, M. Adv. Synth. Catal., 2010, 352, 753-819.
[10]
Fu, B.; Li, N.; Liang, X.M.; Dong, Y.H.; Wang, D.Q. Chinese J. Org. Chem, 2015, 27, 1-4.
[11]
Dixon, D.D.; Grina, J.; Josey, J.A.; Rizzi, J.P.; Schlachter, S.T.; Wallace, E.M.; Wang, B.; Wehn, P.; Yang, H. PCT Int. Appl., WO 2015175845, 2015.
[12]
Zhang, D.Y.; Zhang, R.H.; Zhong, B.Y.; Shi, C. PCT Int. Appl., WO 2014000418, 2014.
[13]
Hughes, G. OShea, P.; Goll, J.; Gauvreau, D.; Steele, J. Tetrahedron, 2009, 65, 3189-3196.
[14]
Ismaiel, A.M.; Gad, L.M.; Ghareib, S.A.; Bamanie, F.H. Moustafa. M.A. Med. Chem. Res., 2009, 18, 745-757.
[15]
Yang, L.L.; Ma, X.B.; Yuan, C.; He, Y.Y.; Li, L.; Fang, S.; Xia, W.; He, T.; Qian, S.; Xu, Z.H.; Li, G.B.; Wang, Z.Y. Eur. J. Med. Chem., 2017, 134, 230-241.
[16]
Yang, L.L.; He, Y.Y.; Chen, Q.L.; Qian, S.; Wang, Z.Y. J. Heterocycl. Chem., 2016, 54, 1457-1466.
[17]
Qian, S.; He, T.; Wang, W.; He, Y.Y.; Zhang, M.; Yang, L.L.; Li, G.B.; Wang, Z.Y. Bioorg. Med. Chem., 2016, 24, 6194-6205.
[18]
Qian, S.; Zhang, M.; He, Y.; Wang, W.; Liu, S. Future Med. Chem., 2016, 8, 1239-1258.
[19]
Evans, P.; Grange, R.; Clizbe, E. Synthesis, 2016, 48, 2911-2968.
[20]
You, S.L.; Zhu, X.Z.; Luo, Y.M.; Hou, X.L.; Dai, L.X. J. Am. Chem. Soc., 2001, 123, 7471-7472.
[21]
Detz, R.J.; Delville, M.M.; Hiemstra, H.; Maarseveen, J.H. Angew. Chem. Int. Ed., 2008, 47, 3837-3840.
[22]
Trost, B.M.; Zhang, T.; Sieber, J.D. Chem. Sci., 2010, 1, 427-440.
[23]
Chen, J.P.; Peng, Q.; Lei, B.L.; Hou, X.L.; Wu, Y.D. J. Am. Chem. Soc., 2011, 133, 14180-14183.
[24]
Ye, K.Y.; He, H.; Liu, W.B.; Dai, L.X.; Helmchen, G.; You, S.L. J. Am. Chem. Soc., 2011, 133, 19006-19014.
[25]
Arnold, J.S.; Nguyen, H.M. J. Am. Chem. Soc., 2012, 134, 8380-8383.
[26]
Arnold, J.S.; Mwenda, E.T.; Nguyen, H.M. Angew. Chem. Int. Ed., 2014, 53, 3688-3692.
[27]
Kawatsura, M.; Uchida, K.; Terasaki, S.; Tsuji, H.; Minakawa, M.; Itoh, T. Org. Lett., 2014, 16, 1470-1473.
[28]
Wang, X.; Guo, P.; Han, Z.; Wang, X.; Wang, Z.; Ding, K. J. Am. Chem. Soc., 2014, 136, 405-411.
[29]
Wu, H.; Xie, F.; Wang, Y.; Zhao, X.; Liu, D.; Zhang, W. Org. Biomol. Chem., 2015, 13, 4248-4254.
[30]
Cai, A.; Guo, W.; Martinez-Rodriguez, L.; Kleij, A.W. J. Am. Chem. Soc., 2016, 138, 14194-14197.
[31]
Huo, X.; He, R.; Fu, J.; Zhang, J.; Yang, G.; Zhang, W. J. Am. Chem. Soc., 2017, 139, 9819-9822.
[32]
Jing, J.; Huo, X.; Shen, J.; Fu, J.; Meng, Q.; Zhang, W. Chem. Commun., 2017, 53, 5151-5154.
[33]
Wang, Y.N.; Wang, B.C.; Zhang, M.M.; Gao, X.W.; Li, T.R.; Lu, L.Q.; Xiao, W.J. Org. Lett., 2017, 19, 4094-4097.
[34]
Xia, C.; Shen, J.; Liu, D.; Zhang, W. Org. Lett., 2017, 19, 4251-4254.
[35]
Zhou, Y.; Breit, B. Chemistry, 2017, 23, 18156-18160.
[36]
Huo, X. Zhang, J.; Fu, J.; He, R.; Zhang, W. J. Am. Chem. Soc., 2018, 140, 2080-2084.
[37]
Jiang, X.; Boehm, P.; Hartwig, J.F. J. Am. Chem. Soc., 2018, 140, 1239-1242.
[38]
Reddy, K.H.V.; Bédier, M.; Bouzbouz, S. Eur. J. Org. Chem., 2018, 1455-1459.

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