Abstract
Reactions of 1,3-bis(bromopentyl)-5(6)-substituted uracyls with a series of five-membered heterocycles containing in the ring N, S, or O atoms and a mercapto group as a substituent at the carbon atom of the ring afforded uracyl derivatives of acyclic and macrocyclic structure with 2-thiobenzoxazole, 2-thio-5-methyl-1,3,4-thiadiazole, 2-thiobenzimidazole, and 2,5-dithio-1,3,4-thiadiazole fragments. N atoms of benzoxazole and imidazole fragments of compounds obtained undergo alkylation and quaternization with alkyl iodides and alkyl tosylates.
Similar content being viewed by others
References
Andrzejewska, M., Yepez-Mulia, L., Tapia, A., Cedillo-Rivera, R., Laudy, A.E., Starosciak, B.J., and Kazimierczuk, Z., Eur. J. Pharm. Sci., 2004, vol. 21, p. 323.
Yang, Y.-H., Cheng, M.-S., Wang, Q.-H., Nie, H., Liao, N., Wang, J., and Chen, H., Eur. J. Med. Chem., 2009, vol. 44, p. 1808.
Ryu, C.-K., Lee, R.-Y., Kim, N.Y., Kim, Y.H., and Song, A.L., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 5924.
McKee, M.L. and Kerwin, S.M., Bioorg. Med. Chem., 2008, vol. 16, p. 1775.
Mirzaei, J., Siavoshi, F., Emami, S., Safari, F., Khoshayand, M.R., Shafiee, A., and Foroumadi, A., Eur. J. Med. Chem., 2008, vol. 43, p. 1575.
Jazayeri, S., Moshafi, M.H., Firoozpour, L., Emami, S., Rajaba-lian, S., Haddad, M., Pahlavanzadeh, F., Esnaashari, M., Shafiee, A., and Foroumadi, A., Eur. J. Med. Chem., 2009, vol. 44, p. 1205.
Reznik, V.S., Anikienko, K.A., Kurochkin, V.K., Akamsin, V.D., Galyametdinova, I.V., and Bychikhin, E.A., Dokl. Akad. Nauk, 1998, vol. 362, p. 68.
Semenov, V.E., Voloshina, A.D., Toroptzova, E.M., Kulik, N.V., Zobov, V.V., Giniyatullin, R.Kh., Mikhailov, A.S., Nikolaev, A.E., Akamsin, V.D., and Reznik, V.S., Eur. J. Med. Chem., 2006, vol. 41, p. 1093.
Anikienko, K.A., Bychikhin, E.A., Reznik, V.S., Akamsin, V.D., Galyametdinova, I.V. Chem.-biol. interact., 2008, vol. 175, p. 286.
Semenov, V.E., Akamsin, V.D., and Reznik, V.S., Zh. Obshch. Khim., 2007, vol. 77, p. 1353.
Giniyatullin, R.Kh., Mikhailov, A.S., Semenov, V.E., Akamsin, V.D., Reznik, V.S., Chernova, A.V., Doroshkina, G.M., Nafikova, A.A., Latypov, Sh.K., Efremov, Yu.Ya., Sharafutdinova, D.R., Gubaidullin, A.T., and Litvinov, I.A. Izv. AN. Ser. Khim., 2003, vol. 52, p. p. 1511.
Semenov, V., Gubaidullin, A., Kataeva, O., Lodochnikova, O., Timosheva, A., Kataev, V., Giniyatullin, R., Nikolaev, A., Chernova, A., Shagidullin, R., Nafikova, A., and Reznik, V., Struct. Chem., 2006, vol. 17, p. 409.
Sandstrom, J., Adv. Heterocycl. Chem., 1968, vol. 9, p. 165.
McClellan, L., Tables of Experimental Dipole Moments, San-Francisko: Freeman & Co., 1963, vol. 1.
Minkin, V.I., Osipov, O.A., and Zhdanov, Yu.A., Dipol’nye momenty v organicheskoi khimii (Dipole Moments in Organic Chemistry), Leningrad: Khimiya, 1968.
Semenov, V.E., Nikolaev, A.E., Kozlov, A.V., Efremov, Yu Ya., Latypov, Sh.K., and Reznik, V.S., Zh. Org. Khim., 2008, vol. 44, p. 890.
Nikolaev, A.E., Semenov, V.E., Sharafutdinova, D.R., Efremov, Y.Y., and Reznik, V.S., Tetrahedron Lett., 2008, vol. 49, p. 5994.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © E.S. Krylova, V.E. Semenov, I.V. Galyametdinova, V.D. Akamsin, D.R. Sharafutdinova, V.S. Reznik, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 741–747.
Rights and permissions
About this article
Cite this article
Krylova, E.S., Semenov, V.E., Galyametdinova, I.V. et al. Uracyl derivatives functionalized with N-, S-, O-heterocycles. Russ J Org Chem 47, 746–752 (2011). https://doi.org/10.1134/S1070428011050149
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428011050149