Abstract
Co-oligomerization of N-vinylpyrroles (N-vinyl-2,3-dimethylpyrrole, N-vinyl-2-phenylpyrrole, N-vinyl-2,3-diphenylpyrrole, N-vinyl-2-(2-thienyl)pyrrole, and N-vinyl-2-[1-(4,5,6,7-tetrahydroindolyl) ethyl]-4,5,6,7-tetrahydroidole) with N-vinylpyrrolidone in the presence of a radical initiator (AIBN) gives co-oligomers with molecular masses of 1600–5200 in up to 87% yield. The products are readily soluble in organic solvents (benzene, 1,4_dioxane, and chloroform), and in the case of high N-vinylpyrrolidone content, also in ethanol and in water. The co-oligomers are non-toxic or have low toxicity (the lethal dose LD50 = 1300–2000) and possess biological activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., eds., London: Pergamon, 1979, vol. 4. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1985, vol. 8.
Gur’yanov, I.D., Karamova, N.S., Yusupova, D.V., Gnezdilov, O.I., and Koshkarova, L.A., Bioorg. Khim. 2013, vol. 39, no. 1, pp. 121–128.
Montaner, B., Navarro, S., Pique, M., Vilaseca, M., Martinell, M., Giralt, E., Gil, J., and Perez-Tomas, R., J. Pharmacol., 2000, vol. 131, pp. 585–593.
Llagostera, E., Soto-Cerrato, V., Joshi, R., Montaner, B., Gimenez-Bonafe, P., and Perez-Tomas, R., Anticancer Drugs, 2005, vol. 16, no. 4, pp. 393–399.
Azuma, T., Watanabe, N., Yagisawa, H., Hirata, H., Iwamura, M., and Kobayashi, Y., Immunopharmacology, 2000, vol. 46, pp. 29–37.
Mikhaleva, A.I., Markova, M.V., Tatarinova, I.V., Morozova, L.V., and Trofimov, B.A., Vysokomol. Soedin., Ser. B, 2014, vol. 56, no. 4, pp. 401–422.
The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, Rappoport, Z. and Liebman, J.F., eds., Chichester: Wiley, 2008.
Comprehensive Organic Name Reactions and Reagents, Wang, Z., ed., London: Wiley, 2009, Part 3, pp. 2793–2796.
Trofimov, B.A., Mikhleva, A.I., Shmidt, E.Yu., and Sobenina, L.N., Khimiya pirrola. Novye stranitsy (The Chemistry of Pyrrole. New Pages), Novosibirsk: Nauka, 2012.
Soldatenkov, A.T., Le Tuan An, Kolyadina, N.M., Il’in, A.P., and Chyong Hong Chieu, Lekarstva. Prikladnoi tonkii organicheskii sintez (Drugs. Applied Fine Organic Synthesis), Khanoi: Znanie, 2014.
Sidel’kovskaya, F.P., Khimiya N-vinilpirrolidona i ego polimerov (The Chemistry of N-Vinylpyrrolidone and Its Polymers), Moscow: Nauka, 1970.
Trofimov, B.A. and Mikhaleva, A.I., N-Vinilpirroly (N-Vinylpyrroles), Novosibirsk: Nauka, 1984.
Shostakovskii, M.F., Sidel’kovskaya, F.I., Atavin, A.S., et al., Vysokomol. Soedin., Ser. B, 1971, vol. 13, no. 11, pp. 847–850.
Rabek, J.F., Experimental Methods in Polymer Chemistry, New York: Wiley, 1980. Translated under the title Eksperimental’nye metody v khimii polimerov, Moscow: Mir, 1983.
Zil’berman, E.N., Vysokomol. Soedin., Ser. B, 1979, vol. 21, no. 1, pp. 33–36.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © M.V. Markova, A.V. Ivanov, B.A. Trofimov, 2018, published in Doklady Akademii Nauk, 2018, Vol. 482, No. 6.
Rights and permissions
About this article
Cite this article
Markova, M.V., Ivanov, A.V. & Trofimov, B.A. Free-Radical Co-Oligomerization of N-Vinylpyrroles with N-Vinylpyrrolidone: A Route to New Bioactive Oligomers. Dokl Chem 482, 237–241 (2018). https://doi.org/10.1134/S0012500818100075
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0012500818100075