Abstract
4-Phenyl derivatives of spinaceamine and spinacine undergo mild catalytic hydrogenation under atmospheric pressure with cleavage of the C4ÄN5 bond to give 5-benzyl-substituted histamines and histidines. The process is likely to be facilitated by the double benzylic effect on the CÄN bond of the imidazole and benzene rings.
Similar content being viewed by others
REFERENCES
Stocker, F.B., Fordice, M.W., Larson, J.K., and Thorstenson, J.H., J. Org. Chem., 1966, vol. 31, no. 7, pp. 2380-2383.
Vitali, T., Mossini, F., and Bertassini, G., Farmaco, Ed. Sci., 1967, vol. 22, no. 10, pp. 821-845.
Emmett, J.C., Durant, G.J., Ganellin, C.R., Koe, A., and Turner, J.L., J. Med. Chem., 1982, vol. 25, no. 1, pp. 1168-1174.
Yutilov, Yu.M., Abramyants, M.G., and Smolyar, N.N., Russ. J. Org. Chem., 1995, vol. 31, no. 10, pp. 1429-1430.
Aldrich Library of NMR Spectra, 2nd ed., vol. 2, C, p. 486.
Heyl, D., Harris, S.A., and Folkers, K., J. Am. Chem. Soc., 1948, vol. 70, no. 10, pp. 3429-3431.
Casella, L. and Gullotti, M., J. Am. Chem. Soc., 1981, vol. 103, no. 21, pp. 6338-6347.
Black, J.W., Duncan, W.A.M., Durant, C.J., Ganellin, C.R., and Parsons, E.M., Nature, 1972, vol. 239, no. 4, pp. 385-390.
Grechishkin, L.L., Gol'dfarb, V.L., Gavrovskaya, L.K., and Brovtsina, N.B., Farmakol. Toksikol., 1973, no. 3, pp. 197-203.
Shlevkov, B.A., Agafonova, N.A., and Pryanishnikov, A.S., Med. Pom., 1995, no. 4, pp. 44-46.
Gushchin, I.S., Terapevt. Arkhiv, 1997, no. 10, pp. 27-34.
Uspenskii, V.I., Gistamin (Histamine), Moscow: Gos. Izd. Med. Lit., 1963.
Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Khar'kov: Torsing, 1998, vol. 1, p. 273.
Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon Press, 1979, vol. 5. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1986, vol. 10, p. 382.
Mashkovskii, M.D., Lekarstvennye sredstva (Drugs), Khar'kov: Torsing, 1998, vol. 2, p. 130.
Cain, M., Guzman, F., Cook, J.M., Rice, K.C., and Skolnick, Ph., Heterocycles, 1982, vol. 19, no. 6, pp. 1003-1007.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Yutilov, Y.M., Abramyants, M.G. & Smolyar, N.N. Hydrogenation of 4-Phenylspinaceamines and Synthesis of 5-Benzylhistamines. Russian Journal of Organic Chemistry 37, 119–124 (2001). https://doi.org/10.1023/A:1012346021943
Issue Date:
DOI: https://doi.org/10.1023/A:1012346021943