Abstract
The cyclization of (2-bromophenyl)thioacetic acid morpholide to 2-(morpholin-4-yl)-1-benzothiophene in the presence of copper(II) chloride has been found to involve intermediate formation of a complex consisting of two thioamide molecules and one copper cation. The complex has been isolated, and its molecular structure parameters have been determined by quantum chemical calculations.
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Antipin, I.S., Kazymova, M.A., Kuznetsov, M.A., Vasilyev, A.V., Ishchenko, M.A., Kiryushkin, A.A., Kuznetsova, L.M., Makarenko, S.V., Ostrovskii, V.A., Petrov, M.L., Solod, O.V., Trishin, Yu.G., Yakovlev, I.P., Nenaidenko, V.G., Beloglazkina, E.K., Beletskaya, I.P., Ustynyuk, Yu.A., Solov’ev, P.A., Ivanov, I.V., Malina, E.V., Sivova, N.V., Negrebetskii, V.V., Baukov, Yu.I., Pozharskaya, N.A., Traven’, V.F., Shchekotikhin, A.E., Varlamov, A.V., Borisova, T.N., Lesina, Yu.A., Krasnokutskaya, E.A., Rogozhnikov, S.I., Shurov, S.N., Kustova, T.P., Klyuev, M.V., Khelevina, O.G., Stuzhin, P.A., Fedorov, A.Yu., Gushchin, A.V., Dodonov, V.A., Kolobov, A.V., Plakhtinskii, V.V., Orlov, V.Yu., Kriven’ko, A.P., Fedotova, O.V., Pchelintseva, N.V., Charushin, V.N., Chupakhin, O.N., Kliochkin, Yu.N., Klimochkina, A.Yu., Kuryatnikov, V.N., Malinovskaya, Yu.A., Levina, A.S., Zhuravlev, O.E., Voronchikhina, L.I., Fisyuk, A.S., Aksenov, A.V., Aksenov, N.A., and Aksenova, I.V., Russ. J. Org. Chem., 2017, vol. 53, no. 9, p. 1275. https://doi.org/10.1134/S1070428017090019
Androsov, D.A., Popova, E.A., Petrov, M.L., and Ponyaev, A.I.,Russ. J. Gen. Chem., 2014, vol. 84, no. 12, p. 2405. https://doi.org/10.1134/S1070363214120093
Grese, T.A., Pennington, L.D., Sluka, J.P., Adrian, M.D., Cole, H.W., Fuson, T.R., Magee, D.E., Phillips, D.L., Rowley, E.R., Shetler, P.K., Short, L.L., Venugopalan, M., Yang, N.N., Sato, M., Glasebrook, A.L., and Bryant, H.U., J. Med. Chem., 1998, vol. 41, no. 8, p. 1272. https://doi.org/10.1021/jm970688z
Lee, K.C., Moon, B.C., Lee, J.H., Chung, K.-H., Katzenellenbogen, J.A., and Chi, D.Y., Bioorg. Med. Chem., 2003, vol. 11, no. 17, p. 3649. https://doi.org/10.1016/S0968-0896(03)00362-6
Petrov, M.L., Popova, E.A., and Androsov, D.A., Russ. J. Org. Chem., 2015, vol. 51, no. 7, p. 1040. https://doi.org/10.1134/S1070428015070283
Garipov, R.R., Cand. Sci. (Phys.-Math.) Dissertation, Kazan, 2005.
Vijayan, P., Viswanathamurthi, P., Velmurugan, K., Nandhakumar, R., Balakumaran, M.D., Kalaichelvan, P.T., and Malecki, J.G., RSC Adv., 2015, vol. 5, p. 103321. https://doi.org/10.1039/C5RA18568H
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A.Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Coslowski, J., and Fox, D.J., Gaussian 09, Revision A.01, Wallingford CT: Gaussian, 2009.
Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648. https://doi.org/10.1063/1.464913
Funding
This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 785.00X6019) using the facilities of the Chemical Analysis and Materials Research Centre at the St. Petersburg State University.
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Petrov, M.L., Popova, E.A., Krivchun, M.N. et al. Synthesis and Structure of the Copper(II) Chloride Complex with (2-Bromophenyl)thioacetic Acid Morpholide. Russ J Gen Chem 90, 858–862 (2020). https://doi.org/10.1134/S1070363220050163
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DOI: https://doi.org/10.1134/S1070363220050163