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Mannich reaction in a number of six-membered heterocyclic γ-ketones. XI. Aminomethylation of 2, 2, 5-trimethyl-4-oxotetrahydropyran and 2, 2, 5-trimethyl-4-oxotetrahydrothiapyran and reduction of the resulting amino ketones

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Abstract

The structural specificity of the aminomethylation of 2,2,5-trimethyl-substituted 4-oxotetrahydropyran and 4-oxotetrahydrothiapyran was investigated by a study of the structures of the resulting amino ketones by PMR spectroscopy and mass spectrometry. It is shown that the reaction is directed exclusively to the tertiary carbon atom adjacent to the carbonyl group and leads to the corresponding 5-(dimethylaminomethyl)-substituted derivatives. Reduction of the products with lithium aluminum hydride and aluminum isopropoxide in both cases also gives only one spatial isomer of the amino alcohols, the structure of which was established by means of the PMR and IR spectra.

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Literature cited

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Authors and Affiliations

  1. M. V. Lomonosov Moscow Institute of Fine Chemical Technology, USSR

    E. T. Golovin, B. M. Glukhov & B. V. Unkovskii

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  1. E. T. Golovin
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  2. B. M. Glukhov
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  3. B. V. Unkovskii
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Additional information

See [1] for communication X.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 617–620, May, 1976.

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Golovin, E.T., Glukhov, B.M. & Unkovskii, B.V. Mannich reaction in a number of six-membered heterocyclic γ-ketones. XI. Aminomethylation of 2, 2, 5-trimethyl-4-oxotetrahydropyran and 2, 2, 5-trimethyl-4-oxotetrahydrothiapyran and reduction of the resulting amino ketones. Chem Heterocycl Compd 12, 517–520 (1976). https://doi.org/10.1007/BF00470102

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  • DOI: https://doi.org/10.1007/BF00470102

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