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Oxidation of anabasine with hydrogen peroxide

Summary

  1. 1.

    When anabasine is treated with 30% hydrogen peroxide in acetic acid, both the pyridine and piperidine parts of the molecule of this alkaloid are oxidized with formation of δ-(hydroxyimino)-3-pyridinevaleric acid 1-oxide, whose structure was established by studying its reactions and comparing it with a synthetic sample.

  2. 2.

    Reduction of δ-(hydroxyimino)-3-pyridinevaleric acid 1-oxide gives (±)-δ-amino-3-pyridinevaleric acid lactam.

  3. 3.

    The action of 10% aqueous hydrogen peroxide is directed at the piperidine nitrogen atom of the anabasine molecule; as a result of the subsequent transformations the piperidine nucleus undergoes cleavage with formation of δ-(hydroxyimino)-3-pyridinevaleric acid.

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Literature cited

  1. 1.

    V. K. Zvorykina, F. D. Alashev, and Ya. L. Gol'dfarb, Izv. AN SSSR. Otd. khim. n. 788 (1958).

  2. 2.

    A. G. Davies, Organic Peroxides, London, Butterworth, p. 55 (1961).

  3. 3.

    K. Kahr and C. Berther, Chem. Ber.93, 132 (1960); O. L. Lebedev and S. N. Kazarnovskii, Zh. obshch. khimii30, 1631 (1960).

  4. 4.

    E. Ochiai, J. Organ. Chem.18, 534 (1953).

  5. 5. a)

    G. Men'shikov, I. Losik, and A. Orekhov, Khim.-farm. prom.7 (1934)

  6. 5. b)

    G. Menschikoff, J. Lossik, and A. Orechoff, Ber.67, 1157 (1934).

  7. 6.

    J. C. Shivers, M. L. Dillon, and C. R. Hauser, J. Amer. Chem. Soc.69, 119 (1947).

  8. 7.

    M. Ferles and J. Jizba, Chemie Pyridinu, Praha, str. 440 (1957).

  9. 8.

    A. S. Sadykov and R. K. Karimov, Uch. zap. Leninabadskogo gos. ped. instituta, No. 10, p. 119 (1958).

  10. 9.

    A. S. Sadykov and O. S. Otroshchenko, Chemistry, Technology, and Application of Pyridine and Quinoline [in Russian], Riga, p. 89 (1957).

  11. 10.

    F. Späth and L. Mamoli, Ber.69, 1082 (1936).

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Additional information

The authors find it a pleasant duty to thank J. Kovar (Prague) for the sample of 6-oxo-3-pyridinevaleric acid and for describing the method by which it was prepared.

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Gol'dfarb, Y.L., Alashev, F.D. & Zvorykina, V.K. Oxidation of anabasine with hydrogen peroxide. Russ Chem Bull 11, 2112–2117 (1962). https://doi.org/10.1007/BF00911374

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Keywords

  • Hydrogen
  • Nitrogen
  • Acetic
  • Hydrogen Peroxide
  • Acetic Acid