Abstract
The condensation of naphthalen-2-amine with furan-2-carbonyl chloride in propan-2-ol gave N-(naphthalen-2-yl)furan-2-carboxamide which was treated with excess P2S5 in anhydrous toluene to obtain the corresponding thioamide. The oxidation of the latter with potassium hexacyanoferrate(III) in alkaline medium afforded 2-(furan-2-yl)naphtho[2,1-d][1,3]thiazole. A probable mechanism of its formation was proposed, and the ring closure involving C1 of the naphthalene fragment was substantiated by quantum chemical calculations. Electrophilic substitution reactions of 2-(furan-2-yl)naphtho[2,1-d][1,3]thiazole (nitration, bromination, formylation, and acylation) involved exclusively the 5-position of the furan ring.
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Aleksandrov, A.A., El’chaninov, M.M., Makarova, N.I., and Luk’yanov, B.S., Chem. Heterocycl. Compd., 2011, vol. 47, p.690.
Sherman, W.R. and Dickson, D.E., J. Org. Chem., 1962, vol. 27, p. 1351.
Jacobson, P., Ber., 1886, vol. 19, p. 1067; ibid., p. 1811.
Farcasan, V. and Makkay, C., Acad. Repub. Pop. Rom., Fil. Cluj, Stud. Cercet. Chim., 1959, vol. 10, p.145.
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., 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., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Wallingford CT: Gaussian, 2003.
El’chaninov, M.M., Oleinikova, L.Ya., and Simonov, A.M., Chem. Heterocycl. Compd., 1979, vol. 15, p.856.
Dorofeenko, G.N., Zh. Obshch. Khim., 1961, vol. 31, p.994.
Pozharskii, A.F., Teoreticheskie osnovy khimii geterotsiklov (Theoretical Foundations of the Chemistry of Heterocycles), Moscow: Khimiya, 1985, p. 126.
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Original Russian Text © A.A. Aleksandrov, M.M. El’chaninov, V.F. Stepanov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 7, pp. 1011–1014.
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Aleksandrov, A.A., El’chaninov, M.M. & Stepanov, V.F. Synthesis, Structure, and Reactivity of Naphtho-Fused 2-(Furan-2-yl)-1,3-thiazole. Russ J Org Chem 54, 1014–1017 (2018). https://doi.org/10.1134/S1070428018070072
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DOI: https://doi.org/10.1134/S1070428018070072