Abstract
5-(1H-Pyrrol-2-ylmethyl)-4H-thieno[3,2-b]pyrroles were synthesized by condensation of N-substituted (4H-thieno[3,2-b]pyrrol-5-yl)methanols with pyrrole in the presence of Amberlyst 15 as catalyst. Treatment of the products with N-bromosuccinimide led to the formation of dark blue polymers insoluble in organic solvents.
Similar content being viewed by others
References
Hemetsberger, H. and Knittel, D., Monatsh. Chem., 1972, vol. 103, p. 194. https://doi.org/10.1007/BF00912944
Yarovenko, V.N., Semenov, S.L., Zavarzin, I.V., Ignatenko, A.V., and Krayushkin, M.M., Russ. Chem. Bull., Int. Ed., 2003, vol. 52, p. 451. https://doi.org/10.1023/A:1023435605723
Ashok, D., Gold, P., Sravan, D., Rajach, J., Sarasja, M., and Bhaskar, K., Indian J. Heterocycl. Chem., 2011, vol. 20, p. 81.
Ilyin, A.P., Dmitrieva, I.G., Kustova, V.A., Manaev, A.V., and Ivachtchenko, A.V., J. Comb. Chem., 2007, vol. 9, p. 96. https://doi.org/10.1021/cc060091h
Sartori, L., Mercurio, C., Amigoni, F., Cappa, A., Faga, G., Fattori, R., Legnaghi, E., Ciossani, G., Mattevi, A., Meroni, G., Moretti, L., Cecatiello, V., Pasqualato, S., Romussi, A., Thaler, F., Trifiro, P., Villa, M., Vultaggio, S., Botrugno, O.A., Dessanti, P., Minucci, S., Zagarri, E., Carettoni, D., Iuzzolino, L., Varasi, M., and Vianello, P., J. Med. Chem., 2017, vol. 60, p. 1673. https://doi.org/10.1021/acs.jmedchem.6b01018
Ching, K.-Ch., Tran, T.N.Q., Amrun, S.N., Kam, Y.-W., Ng, L.F.P., and Chai, Ch.L.L., J. Med. Chem., 2017, vol. 60, p. 3165. https://doi.org/10.1021/acs.jmedchem.7b00180
Jones, C., Boudinet, D., Xia, Y., Denti, M., Das, A., Facchetti, A., and Driver, T.G., Chem. Eur. J., 2014, vol. 20, p. 5938. https://doi.org/10.1002/chem.201304914
Torosyan, S.A., Zagitov, V.V., Gimalova, F.A., Biglova, R.Z., and Miftakhov, M.S., Mendeleev Commun., 2018, vol. 28, p. 192. https://doi.org/10.1016/j.mencom.2018.03.028
Oechsle, P. and Paradies, J., Org. Lett., 2014, vol. 16, p. 4086. https://doi.org/10.1021/ol501752f
Nakanishi, H., Sumi, N., Aso, Y., and Otsubo, T., J. Org. Chem., 1998, vol. 63, p. 8632. https://doi.org/10.1021/jo981541y
Yamamoto, T., Morita, A., Miyazaki, Y., Maruyama, T., Wakayama, H., Zhou, Z.H., Nakamura, Y., Kanbara, T., Sasaki, S., and Kubota, K., Macromolecules, 1992, vol. 25, p. 1214. https://doi.org/10.1021/ma00030a003
Acknowledgments
The spectral and analytical data were obtained using the equipment of the Chemistry Joint Center (Ufa Institute of Chemistry, Russian Academy of Sciences) and Agidel Regional Joint Center (Ufa Research Center, Russian Academy of Sciences).
Funding
This study was performed in the framework of state assignment (project no. AAAA-A17-117011910032-4) and under financial support by the Russian Foundation for Basic Research (project no. 19-33-90113).
Author information
Authors and Affiliations
Corresponding author
Additional information
Conflict of Interests
The authors declare the absence of conflict of interests.
Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1921–1925.
Rights and permissions
About this article
Cite this article
Torosyan, S.A., Nuriakhmetova, Z.F., Gimalova, F.A. et al. New 4-Substituted 5-(1H-Pyrrol-2-ylmethyl)-4H-thieno[3,2-b]pyrroles and Their Reactions with N-Bromosuccinimide. Russ J Org Chem 55, 1907–1911 (2019). https://doi.org/10.1134/S1070428019120169
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428019120169