Abstract
β,γ-Unsaturated ketones (such as cyclohexylideneacetophenone) are formylated with dichloromethyl butyl ether in the presence of anhydrous aluminum chloride. A method has been developed for the synthesis of 3-aryl-substituted 5,6,7,8-tetrahydro-2-benzopyrilium salts unsubstituted in 1 position. The thus-synthesized salts are converted into the corresponding 5,6,7,8-tetrahydroisoquinolines.
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G. N. Dorofeenko and V. I. Dulenko, DAN, 157, 361, 1964.
L. V. Dulenko, V. I. Dulenko, and G. N. Dorofeenko, ZhOKh, 34, 3588, 1964.
G. N. Dorofeenko, G. P. Safaryan, and V. I. Dulenko, ZhOKh, 36, 811, 1966.
A. Rieche, H. Gross, and E. Höft, Chem. Ber. 93, 88, 1960.
V. V. Moiseev and L. P. Zalukaev, Izvestiya Vuz. ser. khim., 8, 945, 1967.
A. D. Semenov, G. N. Dorofeenko, and V. I. Dulenko, KhGS [Chemistry of Heterocyclic Compounds], 14, 1966.
A. T. Balaban, G. D. Mateescu, and M. Elian, Tetrah., 18, 1053, 1962.
A. Cross, Introduction to Practical Infrared Spectroscopy [Russian translation], IL, Moscow, 106, 1961.
L. Bellamy, The Infrared Spectra of Complex Molecules, Methuen, 1958.
A. R. Katritzky, ed., Physical Methods in Heterocyclic Chemistry [Russian translation], Khimiya, Moscow, 506, 1966.
R. Grew, Naturwiss., 33, 333, 1946; Ber., 81, 279, 1948.
M. D. Jarrow and G. A. R. Kon, J. Chem. Soc., 128, 2188, 1926.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 585–587, May, 1970.
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Dorofeenko, G.N., Safaryan, G.P. Synthesis of 3-aryl-5,6,7,8-tetrahydro-2-benzopyrilium salts and corresponding isoquinolines. Chem Heterocycl Compd 6, 538–540 (1970). https://doi.org/10.1007/BF00500665
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DOI: https://doi.org/10.1007/BF00500665