A simple and effective method for the synthesis of substituted imidazo[1,2-a]pyridin-3-yl-acetic acids has been developed based on the multicomponent condensation of 2-aminopyridines with arylglyoxals and Meldrum's acid.
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Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40, 1170.
Fisher, M. H.; Lusi, A. J. Med. Chem. 1972, 15, 982.
Hamdouchi, C.; Blas, J.; del Prado, M.; Gruber, J.; Heinz, B. A.; Vance, L. J. Med. Chem. 1999, 42, 50.
Rupert, K. C.; Henry, J. R.; Dodd, J. H.; Wadsworth, S. A.; Cavender, D. E.; Olini, G. C.; Fahmy, B.; Siekierka, J. Bioorg. Med. Chem. Lett. 2003, 13, 347.
Hamdouchi, C.; Zhong, B.; Mendoza, J.; Collins, E.; Jaramillo, C.; De Diego, J. E.; Robertson, D.; Spencer, C. D.; Anderson, B. D.; Watkins, S. A.; Zhang, F.; Brooks, H. B. Bioorg. Med. Chem. Lett. 2005, 15, 1943.
Tully, W. R.; Gardner, C. R.; Gillespie, R. J.; Westwood, R. J. Med. Chem. 1991, 34, 2060.
Goodacre, S. C.; Street, L. J.; Hallett, D. M.; Crawforth, J. M.; Kelly, S.; Owens, A. P.; Blackaby, W. P.; Lewis, R. T.; Stanley, J.; Smith, A. J.; Ferris, P.; Sohal, B.; Cook, S. M.; Pike, A.; Brown, N.; Wafford, K. A.; Marshall, G.; Castro, J. L.; Atack, J. R. J. Med. Chem. 2006, 49, 35.
Lemmer, B. Physiol. Behav. 2007, 90, 285.
Kaplan, J.-P.; George, P. US Patent 4382938; Chem. Abstr. 1982, 97, 92280.
Nair, D. K.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2012, 14, 4580.
Marcinkowska, M.; Kołaczkowski, M.; Kaminski, K.; Bucki, A.; Pawłowski, M.; Siwek, A.; Karcz, T.; Mordyl, B.; Starowicz, G.; Kubowicz, P.; Pekala, E.; Wesołowska, A.; Samochowiec, J.; Mierzejewski, P.; Bienkowski, P. Eur. J. Med. Chem. 2016, 124, 456.
Su, H.; Wang, L.; Rao, H.; Xu, H. Org. Lett. 2017, 19, 2226.
Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.
Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323.
Peshkov, V. A.; Peshkov, A. A.; Pereshivko, O. P.; Van Hecke, K.; Zamigaylo, L. L.; Van der Eycken, E. V.; Gorobets, N. Yu. ACS Comb. Sci. 2014, 16, 535.
Gorbunov, Yu. O.; Lichitsky, B. V.; Komogortsev, A. N.; Mityanov, V. S.; Dudinov, A. A.; Krayushkin, M. M. Chem. Heterocycl. Compd. 2018, 54, 692. [Khim. Geterotsikl. Soedin. 2018, 54, 692.]
Wang, P.; Tao, W.-J.; Sun, X.-L.; Liao, S.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 16849.
Kutsunugi, Y.; Kawai, S.; Nakashima, T.; Kawai, T. New J. Chem. 2009, 33, 1368.
Tafelska-Kaczmarek, A.; Prewysz-Kwinto, A.; Skowerski, K.; Pietrasiak, K.; Kozakiewicz, A.; Zaidlewicz, M. Tetrahedron: Asymmetry 2010, 21, 2244.
Lange, J.; Karolak-Wojciechowska, J.; Wejroch, K.; Rump, S. Acta Pol. Pharm. 2001, 58, 43.
Yang, R. F.; Li, Yu. F.; Li, Yo. Z.; Zhao, N.; Yun, L. H.; Qin, J. J.; Feng, Z. Y.; Zhang, Y. Z. EP Patent 2586780.
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Lichitsky, B.V., Tretyakov, А.D., Komogortsev, A.N. et al. Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum’s Acid. Chem Heterocycl Comp 55, 156–159 (2019). https://doi.org/10.1007/s10593-019-02432-6
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DOI: https://doi.org/10.1007/s10593-019-02432-6