Abstract
The reaction of (ethoxymethylidene)cyanoacetic ester with arylamides of acetoacetic acid proceeds under heating in the presence of triethylamine or at room temperature in the presence of sodium ethoxide. According to the NMR and IR data, the intermediate adduct undergoes no other transformations but azacyclization which predominantly involves the cyano group and forms ethyl 5-acetyl-1-aryl-6-hydroxy-2-imino-1,2-dihydropyridine-3-carboxylates in yields of 30–78%. In some cases, 5-acetyl-1-aryl-2-hydroxy-6-oxo-1,6-dihydropyridine-3-carbonitriles resulting from cyclization involving the ethoxycarbonyl group were isolated as minor products (3–12%).
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References
Ismail, M.M.F. and Noaman, E., Med. Chem. Res., 2005, vol.14, p.382. doi https://doi.org/10.1007/s00044-006-0146-2
Li, Z., Liu, Z., Cho, D.W., Zou, J., Gong, M., Breece, R.M., Galkin, A., Li, L., Zhao, H., Maestas, G.D., Tierney, D.L., Herzberg, O., Mariano, D.D., and Mariano, P.S., J. Inorg. Biochem., 2011, vol.105, p.509. doi https://doi.org/10.1016/j.jinorgbio.2010.12.012
Dyachenko, V.D. and Tkachev, R.P., J. Org. Chem., 2003, vol 39, p. 757. doi https://doi.org/10.1023/B:RUJO.0000003153.20325.22
Dyachenko, V.D., Tkachev, R.P., and Bitukova, O.S., J. Org. Chem., 2008, vol.44, p.1565. doi https://doi.org/10.1134/S1070428008110018
Sargsyan, M.S., Ayotsyan, S.S., Asratyan, A.G., Khachatryan, A.Kh., Badasyan, A.E., and Kon’kova, S.G., Khim. Zh. Arm., 2014, vol.67, p.262.
Dyachenko, A.D., Desenko, S.M., Dyachenko, V.D., and Litvinov, V.P., Chem. Heterocycl. Comp., 2000, vol.36, p.480. doi https://doi.org/10.1007/BF02269551
Dyachenko, V.D., Nikishin, A.A., and Litvinov, V.P., Chem. Heterocycl. Comp., 1997, p.33873. doi https://doi.org/10.1007/BF02253045
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Russian Text © S.S. Hayotsyan, A.A. Sargsyan, S.G. Kon’kova, A.Kh. Khachatryan, A.E. Badasyan, K.A. Avagyan, M.S. Sargsyan, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 321–325.
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Hayotsyan, S.S., Sargsyan, A.A., Kon’kova, S.G. et al. Synthesis of Substituted 1,2-Dihydropyridines by the Reaction of (Ethoxymethylidene)cyanoacetic Ester and Arylamides of Acetoacetic Acid. Russ J Org Chem 55, 282–286 (2019). https://doi.org/10.1134/S107042801902026X
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DOI: https://doi.org/10.1134/S107042801902026X