Abstract
1,3,3-Trimethyl-3,4-dihydroisoquinolines, which exist in the imine form, undergo C- hydroxyalkylation upon reaction with hexafluoroacetone and esters of trifluoropyruvic acid at the C1 CH3 group at 20°C. The products with the ketoesters are converted upon heating to γ-lactams. Derivatives of 1,3,3-trimethyl-3,4-dihydroisoquinoline substituted at C1 CH3 group and existing in the enamine form, react with esters of trifluoropyruvic acid at 20°C to give exclusively γ-lactams and do not give reaction products with hexafluoroacetone.
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N. D. Chkanikov, V. D. Sviridov, A. E. Zelenin, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 383 (1990).
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A. E. Zelenin, N. D. Chkanikov, A. M. Umnov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 2074 (1986).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1405–1410, June, 1990.
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Sviridov, V.D., Chkanikov, N.D., Galakhov, M.V. et al. Reactions of polyfluorocarbonyl compounds with 1,3,3-trimethyl-3,4-dihydroisoquinoline and its derivatives. Russ Chem Bull 39, 1268–1272 (1990). https://doi.org/10.1007/BF00962396
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DOI: https://doi.org/10.1007/BF00962396