Abstract
Thiocyanation of secondary enamines of the 3,3-dialkyl-1,2,3,4-tetrahydroisoquinoline series and their benzo[f]-fused analogs (esters, amides, ketones, and nitriles) with thiocyanogen generated in situ afforded thiazolo[4,3-a]isoquinoline derivatives. Analogous reaction with a tertiary enamino ketone gave product of hydrogen substitution at the β-carbon atom of the enamine fragment.
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Vnutrimolekulyarnoe vzaimodeistvie nitril’noi i aminogrupp (Intramolecular Interaction of Cyano and Amino Groups), Babichev, F.S., Ed., Kiev: Naukova Dumka 1987, p. 74.
Shklyaev, V.S., Aleksandrov, B.B., Legotkina, G.I., Vakhrin, M.I., Gavrilov, M.S., and Mikhailovskii, A.G., Chem. Heterocycl. Compd. 1983, vol. 19, p. 1242.
Aleksandrov, B.B., Gavrilov, M.S., Vakhrin, M.I., and Shklyaev, V.S., Chem. Heterocycl. Compd. 1985, vol. 21, p. 1038.
Shklyaev, V.S., Aleksandrov, B.B., Mikhailovskii, A.G., and Vakhrin, M.I., Chem. Heterocycl. Compd. 1989, vol. 25, p. 1038.
Aleksandrov, B.B., Shklyaev, V.S., and Shklyaev, Yu.V., Chem. Heterocycl. Compd. 1992, vol. 28, p. 314.
Surikova, O.V. and Mikhailovskii, A.G., Russ. J. Org. Chem. 2014, vol. 50, p. 1306.
Mikhailovskii, A.G., Yusov, A.S., and Gashkova, O.V., Russ. J. Org. Chem. 2015, vol. 51, p. 1818.
Mikhailovskii, A.G., Yusov, A.S., and Gashkova, O.V., Russ. J. Org. Chem. 2016, vol. 52, p. 223.
Mikhailovskii, A.G., Korchagin, D.V., Gashkova, O.V., and Yusov, A.S., Russ. J. Org. Chem. 2016, vol. 52, p. 1339.
Mikhailovskii, A.G., Korchagin, D.V., Yusov, A.S., and Gashkova, O.V., Chem. Heterocycl. Compd. 2016, vol. 52, p. 852.
Mikhailovskii, A.G., Yusov, A.S., Korchagin, D.V., and Gashkova, O.V., Russ. J. Org. Chem. 2017, vol. 53, p. 790.
Becker, H.G.O., et al., Organikum. Organischchemisches Grundpraktikum, Weinheim: Wiley, 2004, 22nd edn. Translated under the title Organikum, Moscow: Mir 2008, vol. 1, p. 448.
Mikhailovskii, A.G., Polygalova, N.N., Limanskii, E.S., Ismailova, N.G., Syropyatov, B.Ya., and Vakhrin, M.I., Pharm. Chem. J. 2008, vol. 42, no. 2, p. 68.
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Original Russian Text © A.G. Mikhailovskii, D.A. Peretyagin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 12, pp. 1801–1804.
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Mikhailovskii, A.G., Peretyagin, D.A. Thiocyanation of Enamines of the 3,3-Dialkyl-1,2,3,4-tetrahydroisoquinoline Series. Russ J Org Chem 54, 1815–1818 (2018). https://doi.org/10.1134/S1070428018120138
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DOI: https://doi.org/10.1134/S1070428018120138