Abstract
Effect of the molar ratio between reagents, temperature, and synthesis duration on the yield of 3-pyridylsubstituted 5-amino-1,2,4-triazoles in the reaction of aminoguanidine hydrochloride with pyridinecarboxylic acids under acid catalysis conditions was studied. A single-reactor method for synthesis of 3-pyridyl-substituted 5-amino-1,2,4-triazoles and their hydrochlorides was developed.
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Patent Appl. WO2008/117943A1.
Lipinski, C.A., J. Med. Chem., 1983, vol. 26, no. 1, pp. 1–6.
Ouyang, X., Chen, X., Piatnitski, E.L., et al., Bioorg. Med. Chem. Lett., 2005, vol. 15, no. 23, pp. 5154–5159.
Mishra, L., Ram, V.J., and Kushwaha, D.S., Transition Met. Chem., 1989, vol. 14, no. 5, pp. 384–386.
Ferrer, S., Ballesteros, R., Sambartolome, A., et al., J. Inorg. Biochem., 2004, vol. 98, no. 8, pp. 1436–1446.
Castineiras, A., Tan, B.J., and Garcia-Santos, I., Z. Anorg. allgem. Chem., 2008, vol. 634, no. 15, pp. 2907–2916.
Biemann, K. and Bretschneider, H., Monatsh. Chem., 1958, vol. 89, nos. 4–5, pp. 603–610.
Grinshtein, V.Ya. and Chipen, G.I., Zh. Obshch. Khim., 1961, vol. 31, no. 3, pp. 886–890.
Dolzhenko, A.V., Dolzhenko, A.V., and Chui, W.-K., Heterocycles, 2007, vol. 71, no. 2, pp. 429–436.
Dolzhenko, A.V., Pastorin, G., Dolzhenko, A.V., and Chui, W.-K., Tetrahedron Lett., 2009, vol. 50, no. 18, pp. 2124–2128.
Atkinson, M.R., Komzak, A.A., Parkes, E.A., and Polya, J.B., J. Chem. Soc., 1954, no. 12, pp. 4508–4510.
Chernysheva, A.V., Chernyshev, V.M., Korolenko, P.V., and Taranushich, V.A., Zh. Prikl. Khim., 2008, vol. 81, no. 10, pp. 1690–1695.
Chernyshev, V.M., Chernysheva, A.V., and Taranushich, V.A., Zh. Prikl. Khim., 2009, vol. 82, no. 2, pp. 282–287.
Tarasova, E.V., Chernyshev, V.M., Chernysheva, A.V., and Abagyan, R.S., Zh. Prikl. Khim., 2011, vol. 84, no. 3, pp. 408–414.
Chernyshev, V.M., Chernysheva, A.V., and Starikova, Z.A., Heterocycles, 2010, vol. 81, no. 10, pp. 2291–2311.
Anders, E., Wermann, K., Wiedel, B., and Vanden Eynde, J.-J., Liebigs. Ann., 1997, no. 4, pp. 745–752.
Chernyshev, V.M., Tarasova, E.V., Chernysheva, A.V., and Rybakov, V.B., Acta Crystallogr. Sect. E, 2011, vol. 67, no. 2, pp. o466–o467.
Dvortsak, P., Reiter, J., Somorai, T., and Sohar, P., Magn. Reson. Chem., 1985, vol. 23, no. 3, pp. 194–197.
Pretsch, E., Buhlmann, Ph., and Badertscher, M., Structure Determination of Organic Compounds, Berlin: Springer, 2009.
Claramunt, R.M., Lopez, C., Santa Maria, M.D., et al., Prog. Nucl. Magn. Reson. Spectrosc., 2006, vol. 49, nos. 3–4, pp. 169–206.
Voronkov, M.G., Kashik, T.V., Makarskii, V.V., et al., Doklady Akad. Nauk SSSR, 1976, vol. 227, no. 5, pp. 1116–1119.
Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases, London: Methuen, New York: Wiley, 1962.
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Original Russian Text © V.M. Chernyshev, E.V. Tarasova, A.V. Chernysheva, V.A. Taranushich, 2011, published in Zhurnal Prikladnoi Khimii, 2011, Vol. 84, No. 11, pp. 1804–1810.
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Chernyshev, V.M., Tarasova, E.V., Chernysheva, A.V. et al. Synthesis of 3-pyridyl-substituted 5-amino-1,2,4-triazoles from aminoguanidine and pyridinecarboxylic acids. Russ J Appl Chem 84, 1890–1896 (2011). https://doi.org/10.1134/S1070427211110097
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DOI: https://doi.org/10.1134/S1070427211110097