Abstract
The alkylation of methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate with methyl iodide and allyl, propargyl, and benzyl bromides in the presence of sodium hydride in THF afforded the corresponding N-substituted derivatives. Some reactions of the alkylation products were studied.
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Hemetsberger, H. and Knittel, D., Monatsh. Chem., 1972, vol. 103, p. 194.
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.
Ching, K.-Ch., Kam, Y.-W., Merits, A., Ng, L.F.P., and Chai, Ch.L.L., J. Med. Chem., 2015, vol. 58, p. 9196.
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.
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.
Ashok, D., Goud, P., Shravani, D., Rajaiah, J., Sarasija, M., and Bhaskar, K., Indian J. Heterocycl. Chem., 2010, 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.
Sindac, J.A., Yestrepsky, B.D., Barraza, S.J., Bolduc, K.L., Blakely, P.K., Keep, R.F., Irani, D.N., Miller, D.J., and Larsen, S.D., J. Med. Chem., 2012, vol. 55, p. 3535.
Verbitskiy, E.V., Slepukhin, P.A., Valova, M.S., Cheprakova, E.M., Schepochkin, A.V., Rusinov, G.L., and Charushin, V.N., Eur. J. Org. Chem., 2014, p. 8133.
Krayushkin, M.M., Yarovenko, V.N., Semenov, S.L., Zavarzin, I.V., Ignatenko, A.V., Martynkin, A.Yu., and Uzhinov, B.M., Org. Lett., 2002, vol. 4, p. 3879.
Jones, C., Boudinet, D., Xia, Y., Denti, M., Das, A., Facchetti, A., and Driver, T.G., Chem. Eur. J., 2014, vol. 20, p. 5938.
Jiang, X.-D., Zhang, H., Zhang, Y., and Zhao, W., Tetrahedron, 2012, vol. 68, p. 9795.
De Mico, A., Margarita, R., Parlanti, L., Vescovi, A., and Piancatelli, G., J. Org. Chem., 1997, vol. 62, p. 6974.
Li, J.J., Name reactions: A Collection of Detailed Reaction Mechanisms, New York: Springer, 2003, 2nd ed. Translated under the title Mekhanizmy organicheskikh reaktsii, Moscow: BINOM, 2006, p. 101.
Vostrikov, N.S., Abutkov, A.V., and Miftakhov, M.S., Russ. Chem. Bull., Int. Ed., 2001, vol. 50, p. 1238.
Lotz, S., Landman, M., Goerls, H., Crause, Ch., Nienaber, H., and Olivier, A., Z. Naturforsch. B: Chem. Sci., 2007, vol. 62, no. 3, p. 419.
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Original Russian Text © S.A. Torosyan, F.A. Gimalova, V.V. Zagitov, A.S. Erastov, M.S. Miftakhov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 909–913.
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Torosyan, S.A., Gimalova, F.A., Zagitov, V.V. et al. Synthesis of N-Substituted Methyl 4H-Thieno[3,2-b]pyrrole-5-carboxylates. Russ J Org Chem 54, 912–917 (2018). https://doi.org/10.1134/S1070428018060131
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DOI: https://doi.org/10.1134/S1070428018060131