Abstract
A procedure has been developed for the synthesis of (5-alkenyl-1,2,4-oxadiazol-3-yl)anilines by selective reduction of the nitro group in 5-alkenyl-3-(nitrophenyl)-1,2,4-oxadiazoles. The resulting amines are promising monomers for oxidative and radical polymerizations.
Similar content being viewed by others
References
Heeger, A.J., Angew. Chem., Int. Ed., 2001, vol. 40, no. 14, p. 2591.
Tarasevich, M.R., Orlov, S.B., and Shkol’nikov, E.I., Elektrokhimiya polimerov (Electrochemistry of Polymers), Moscow Nauka, 1990.
Bhadra, S., Khastgir, D., Singha, N.K., and Lee, J.H., Prog. Polym. Sci., 2009, vol. 34, no. 8, p. 783.
Gospodinova, N. and Terlemezyan, L., Prog. Polym. Sci., 1998, vol. 23, no. 8, p. 1443.
Inzelt, G., Conducting Polymers: A New Era in Electrochemistry, Berlin Springer, 2008.
Handbook of Conducting Polymers. Conjugated Polymers: Processing and Applications, Skotheim, T.A. and Reynolds, J.R., Eds., Boca Raton: CRC, 2007, 3rd ed.
Shulga, Y.M., Baskakov, S.A., Abalyaeva, V.V., Efimov, O.N., Shulga, N.Y., Michtchenko, A., Lartundo-Rojas, L., Moreno-R, L.A., Cabañas-Moreno, J.G., and Vasilets, V.N., J. Power Sources, 2013, vol. 224, p. 195.
Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 5, p. 258.
Toth, M., Kun, S., Bokor, E., Benltifa, M., Tallec, G., Vidal, S., Docsa, T., Gergely, P., Somsak, L., and Praly, J.P., Bioorg. Med. Chem., 2009, vol. 17, p. 4773.
Versiani dos Anjos, J., Sinou, D., Srivastava, R.M., Carneiro do Nascimento, S., and de Melo, S.J., J. Carbohydr. Chem., 2008, vol. 27, p. 258.
Schmid, E. and Arndt, F., US Patent no. 4 243 409, 1981.
Conole, D., Beck, T.M., Jay-Smith, M., Tingle, M.D., Eason, C.T., Brimble, M.A., and Rennison, D., Bioorg. Med. Chem., 2014, vol. 22, p. 2220.
Patil, R.D. and Sassona, Y., Org. Chem.: Curr. Res., 2015, vol. 4, no. 4, article ID1000154.
Karunnaya, M.V., Kurbatov, V.G., and Kofanov, E.R., Materialy IVVserossiiskoi konferentsii po organicheskoi khimii. XVII molodezhnaya shkola-konferentsiya po organicheskoi khimii (Proc. IVth All-Russian Conf. on Organic Chemistry. XVIIth Youth School–Conf. on Organic Chemistry), Moscow, 2015, p. 160.
Baykov, S., Sharonova, T., Osipyan, A., Rozhkov, S., Shetnev, A., and Smirnov, A., Tetrahedron Lett., 2016, vol. 57, no. 26, p. 2898. doi: 10.1016/ j.tetlet.2016.05.071
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © M.V. Tarasenko, E.R. Kofanov, S.V. Baikov, G.G. Krasovskaya, A.S. Danilova, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 7, pp. 1072–1076.
Rights and permissions
About this article
Cite this article
Tarasenko, M.V., Kofanov, E.R., Baikov, S.V. et al. Selective reduction of 5-alkenyl-3-(nitrophenyl)-1,2,4-oxadiazoles to 5-alkenyl-3-(aminophenyl)-1,2,4-oxadiazoles. Russ J Org Chem 53, 1085–1089 (2017). https://doi.org/10.1134/S1070428017070211
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428017070211