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- W2605514076 abstract "Acylation of δ-aminovaleric acid is difficult either by the Schotten-Baumann reaction with acetic anhydride and fatty acid chloride or with ketene but aliphatic acylated compound of this amino acid was finally prepared by the Schotten-Baumann reaction with acid chloride after esterification. Dry distillation of this acylated derivatives with equal amount of soda lime gives 2-alkyl-Δ1(or Δ2)-tetrahydropyridine containing γ-coniceine in comparatively high yield. It was doubtful whether the base formed corresponded to formula (I) or (II). Various properties of the compound, such as its ring cleavage to the amino-ketone compound with acid chloride agreed with the α, β-enamine type (II), reported in past literature, but infrared and ultraviolet spectral data indicate that compounds with a substituent with -I effect, such as methyl, in α-position preferentially take the azomethine type (I), while those with electron-withdrawal group, such as phenyl, completely form the azomethine type.Suitable dehydrogenation of the base (I or II) thereby formed gives pyridine compound, such as α-picoline, while catalytic reduction over palladium-carbon gives piperidine derivative, such as dl-coniine." @default.
- W2605514076 created "2017-04-28" @default.
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- W2605514076 date "1959-01-01" @default.
- W2605514076 modified "2023-10-18" @default.
- W2605514076 title "Studies on the Syntheses of Cyclic Nitrogenous Compounds from Amino Acids. IX" @default.
- W2605514076 doi "https://doi.org/10.1248/yakushi1947.79.1_76" @default.
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