Abstract
Nucleophilic addition of secondary heterocyclic amines (morpholine, piperidine, and piperazine) to the double or triple bond of (E)-1,5-diarylpent-2-en-4-yn-1-ones is controlled by the kinetic and thermodynamic factor, respectively. The regioselectivity of the addition of piperazine to these enynones is determined by the substituent nature in the benzene rings. Conjugated ketones with electron-donating substituents take up piperazine molecule at the double bond, and those with electron-withdrawing groups, at the triple bond.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Soldatenkov, A.T., Kolyadina, N.M., and Shendrik, I.V., Osnovy organicheskoi khimii lekarstvennykh veshchestv (Basic Principles of Organic Chemistry of Medicines), Moscow: Khimiya, 2001, p. 75.
Möhrle, H. and Azodi, K., Pharmazie, 2006, vol. 61. no. 10. p. 815.
Boisse, T., Rigo, B., Millet, R., and Hénichart, J.-P., Tetrahedron, 2007, vol. 63. p. 10511.
Bararjanian, M., Balalaie, S., Rominger, F., Movassagh, B., and Bijanzadeh, H.R., J. Org. Chem., 2010, vol. 75. p. 2806.
Tarasenko, K.V., Manoylenko, O.V., Kukhar, V.P., Röschenthaler, G.-V., and Gerus, I.I., Tetrahedron Lett., 2010, vol. 51. p. 4623.
Golovanov, A.A., Odin, I.S., Vologzhanina, A.V., Bekin, V.V., and Nebritova, A.E., Russ. J. Org. Chem., 2014, vol. 50. p. 943.
Shustrova, T.A., Belyaev, N.N., and Stadnichuk, M.D., Zh. Obshch. Khim., 1988, vol. 58. p. 374.
Golovanov, A.A., Gusev, D.M., Vologzhanina, A.V., Bekin, V.V., and Pisareva, V.S., Russ. J. Org. Chem., 2014, vol. 50. p. 13.
Structure Determination of Organic Compounds: Tables of Spectral Data, Pretsch, E., Bühlmann, P., and Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed. Translated under the title Opredelenie stroeniya organicheskikh soedinenii, Moscow: Mir, 2006, p. 295.
Shustrova, T.A., Belyaev, N.N., and Stadnichuk, M.D., Zh. Obshch. Khim., 1985, vol. 55. p. 1777.
Krause, N. and Zelder, C., The Chemistry of Dienes and Polyenes, Rappoport, Z., Ed., Chichester: Wiley, 2000, vol. 2. p. 677.
Bekin, V.V., Pisareva, V.S., and Golovanov, A.A., Bashk. Khim. Zh., 2012, vol. 19. p. 130.
Golovanov, A.A., Latypova, D.R., Bekin, V.V., Pisareva, V.S., Vologzhanina, A.V., and Dokichev, V.A., Russ. J. Org. Chem., 2013, vol. 49. p. 1264.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.A. Golovanov, V.V. Bekin, I.S. Odin, A.Yu. Chertov, O.B. Grigor’eva, V.S. Pisareva, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1723–1727.
Rights and permissions
About this article
Cite this article
Golovanov, A.A., Bekin, V.V., Odin, I.S. et al. Nucleophilic addition of heterocyclic amines to conjugated enyne ketones. Russ J Org Chem 51, 1688–1692 (2015). https://doi.org/10.1134/S1070428015120039
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428015120039