Abstract
Nucleophilic addition of morpholine and piperidine to 1,5-diarylpent-2-en-4-yn-1-ones involves the triple bond in the latter, regardless of the substituents in the aryl rings, to produce the corresponding (E,E)-5-(morpholin-4-yl or piperidin-1-yl)-1,5-diarylpenta-2,4-dien-1-ones in up to 93% yield. According to the X-ray diffraction data, the synthesized compounds in crystal have s-cis and s-trans conformations of the enone and dienone fragments, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Moiseev, I.K., Makarova, N.V., and Zemtsova, M.N., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 2007, vol. 50, p. 3.
Granik, V.G. and Kadushkin, A.V., Enaminy v organicheskom sinteze (Enamines in Organic Synthesis), Shklyaev, V.S., Ed., Yekaterinburg: Ural. Otd. Ross. Akad. Nauk, 1996, p. 3.
Maretina, I.A., Astranyan, G.V., and Ostroumov, I.G., Chem. Heterocycl. Compd., 1992, vol. 28, no. 7, p. 717.
Makarova, N.V., Borenko, E.I., Moiseev, I.K., Pavlova, N.I., Zemtsova, M.N., Nikolaeva, S.N., and Vladyko, G.V., Khim.-Farm. Zh., 2001, vol. 35, no. 9, p. 17.
Prodanchuk, N.G., Megera, I.V., and Patratii, V.K., Khim.-Farm. Zh., 1984, vol. 18, no. 2, p. 173.
Turanova, O.A. and Galyametdinov, Yu.G., Russ. J. Gen. Chem., 2006, vol. 76, p. 1095.
Pashkevich, K.I., Filyakova, V.I., Postovskii, I.Ya., Kechina, A.G., Krukovskii, S.P., Yarosh, A.A., and Ponomarenko, V.A., USSR Inventor’s Certificate no. 763 346, 1978; Byull. Izobret., 1980, no. 34.
Smirnova, Yu.V. and Krasnaya, Zh.A., Russ. Chem. Rev., 2000, vol. 69, no. 12, p. 1021.
Guvingny, T. and Normant, H., Bull. Soc. Chim. Fr., 1960, p. 515.
Bowden, K., Braude, E.A., Jones, E.R.H., and Bedon, B.C.L., J. Chem. Soc., 1946, p. 45.
Utekhina, N.V., Cand. Sci. (Chem.) Dissertation, Togliatti, 1987.
Shustrova, T.A., Belyaev, N.N., and Stadnichuk, M.D., Zh. Obshch. Khim., 1988, vol. 58, p. 374.
Casey, C.P. and Strotman, N.A., J. Org. Chem., 2005, vol. 70, p. 2576.
Bekin, V.V., Pisareva, V.S., and Golovanov, A.A., Bashkir. Khim. Zh., 2012, vol. 19, p. 130.
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.
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.
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.A. Golovanov, I.S. Odin, A.V. Vologzhanina, V.V. Bekin, A.E. Nebritova, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 7, pp. 963–967.
Rights and permissions
About this article
Cite this article
Golovanov, A.A., Odin, I.S., Vologzhanina, A.V. et al. Synthesis of 5-amino-1,5-diarylpenta-2,4-dien-1-ones. Russ J Org Chem 50, 943–947 (2014). https://doi.org/10.1134/S1070428014070045
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428014070045