Abstract
The condensation of ethyl acetoacetate with formaldehyde and primary amines in methanol at 65°C (Mannich reaction) gave up to 92% of hexahydropyrimidine derivatives containing ester and acetyl groups. Analogous reaction with aminopyridines stopped at the stage of formation of linear condensation products.
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Billman, J.H. and Meisenheimer, J.L., J. Med. Chem., 1964, vol. 7, p. 115.
Billman, J.H. and Meisenheimer, J.L., J. Med. Chem., 1965, vol. 8, p. 540.
Groszkowski, S., Korzycka, L., and Bilasiewicz, W., Pol. J. Pharmacol. Pharm., 1973, vol. 25, p. 573.
Siddiqui, A.Q., Merson-Davies, L., and Cullis, P.M., J. Chem. Sos., Perkin Trans. 1, 1999, p. 3243.
Gravier, D., Dupin, J.-P., Casadebaig, F., Hou, G., Boisseau, M., and Bernard, H., Eur. J. Med. Chem., 1989, vol. 24, p. 531.
Horvath, D., J. Med. Chem., 1997, vol. 40, p. 2412.
Shakirov, R.R., Yarmukhamedov, N.N., Vlasova, L.I., Baibulatova, N.Z., Khisamutdinova, R.Yu., Gabdrakhmanova, S.F., Karachurina, L.T., and Baschenko, N.Zh., Khim.-Farm. Zh., 2006, vol. 40, no. 1, p. 29.
Drandarov, K., Guggusbtrg, A., and Hesse, M., Helv. Chim. Acta, 1999, vol. 82, p. 229.
Evans, R.F., Aust. J. Chem., 1967, vol. 20, p. 1643.
Katritzky, A.R., Singh, S.K., and He, H.-Y., J. Org. Chem., 2002, vol. 67, p. 3115.
Bisceglia, J.A., Diaz, J.E., Torres, R.A., and Orelli, L.R., Tetrahedron Lett., 2011, vol. 52, p. 5238.
The Chemistry of the Nitro and Nitroso Groups, Feuer, H., Ed., New York: Interscience, 1970, vol. 2. Translated under the title Khimiya nitro-i nitrozogrupp, Moscow: Mir, 1973, vol. 2, p. 95.
Novikov, S.S., Shvekhgeimer, G.A., Sevost’yanova, V.V., and Shlyapochnikov, V.A., Khimiya alifaticheskikh i alitsiklicheskikh nirosoedinenii (Chemistry of Aliphatic and Alicyclic Nitro Compounds), Moscow: Khimiya, 1974.
Shakirov, R.R., Vlasova, L.I., Shishkin, D.V., Yarmukhamedov, N.N., Baibulatova, N.Z., Semes’ko, D.G., Dokichev, V.A., and Tomilov, Yu.V., Izv. Akad. Nauk, Ser. Khim., 2005, p. 1687.
Shakirov, R.R., Dokichev, T.V., Biglova, R.Z., Vlasova, N.M., Baibulatova, N.Z., and Talipov, R.F., Khim. Geterotsikl. Soedin., 2008, p. 53.
Badamshin, A.G., Baibylatova, N.Z., and Dokichev, V.A., Kinetics, Catalysis and Mechanism of Chemical Reactions. From Pure to Applied Science, Hauppauge, NY: Nova Science, 2011, vol. 1, p. 249.
Cardillo, G. and Tomasini, C., Chem. Soc. Rev., 1996, vol. 25, p. 117.
Fukawa, H., Terao, Y., Achiwa, K., and Sekiya, M., Chem. Pharm. Bull., 1983, vol. 31, p. 94.
Mukhopadhyay, C., Rana, S., and Butcher, R.J., Tetrahedron Lett., 2011, vol. 52, p. 4153.
Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 1. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1982, vol. 2, p. 632.
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Original Russian Text © D.R. Latypova, A.G. Badamshin, A.N. Lobov, V.A. Dokichev, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 6, pp. 860–865.
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Latypova, D.R., Badamshin, A.G., Lobov, A.N. et al. Reaction of ethyl acetoacetate with formaldehyde and primary amines. Russ J Org Chem 49, 843–848 (2013). https://doi.org/10.1134/S1070428013060079
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DOI: https://doi.org/10.1134/S1070428013060079