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Acetylene derivatives

Communication 149. Synthesis of β-amino ketones by the action of secondary amines on β-methoxy ketones and α,β-unsaturated ketones

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Under the influence of mercuric sulfate in methanol solution, tetrahydro-2-methyl-4-(vinylethynyl) pyran-4-ol (I) isomerizes into the divinyl ketone (II). The latter, under the conditions of the reaction unites with methanol and gives the methoxy ketone (III), which on hydrogenation, absorbs one molecule of hydrogen, yielding the saturated methoxy ketone (IV).

  2. 2.

    When methanol is caused to split from the unsaturated methoxy ketone (III, the divinyl ketone (II) is obtained in good yield.

  3. 3.

    By the action of aqueous solutions of dimethylamine and piperidine on the methoxy ketone (III), the amino ketones (V) and (VI) respectively are obtained.

  4. 4.

    By the action of diethylamine (or dibutylamine) on the ketone (VII) or the ketone (VIII), the amino ketone (IX) or (X) is formed.

  5. 5.

    By the action of diethylamine (or dibutylamine) on the ketones (XI), (XII), or (XIII), the diamino ketone (XIV) or (XV) is formed.

  6. 6.

    By the action of dibutylamine on the ketone (XVI) or the ketone (XVII), the amino ketone (XVIII) is obtained, and this, on being hydrogenated, absorbs one molecule of hydrogen and forms the saturated amino ketone (XIX), which is obtained also by the action of dibutylamine on the saturated methoxy ketone (XX).

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Authors and Affiliations

  1. Chemical Institute of the USSR, Academy of Sciences, USSR

    I. N. Nazarov & S. A. Vartanyan

Authors
  1. I. N. Nazarov
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  2. S. A. Vartanyan
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Nazarov, I.N., Vartanyan, S.A. Acetylene derivatives. Russ Chem Bull 2, 287–292 (1953). https://doi.org/10.1007/BF01171000

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  • DOI: https://doi.org/10.1007/BF01171000

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