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2-Aminovinyl ketones Communication 2. Some reactions of alkyl 2-dialkylaminovinyl ketones

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

Summary

  1. 1.

    When alkyl 2-dialkylaminovinyl ketones are hydrogenated, hydrogenolysis of the nitzogen-carbon bond occurs, resulting in the formation of a saturated ketone and a secondary amine.

  2. 2.

    When alkyl 2-dialkylaminovinyl ketones react with hydroxylamine, 5-alkylisozaaoles are formed; this provides a convenient method for the synthesis of these compounds.

  3. 3.

    When alkyl 2-dialkylaminovinyl ketones react with 2-cyanoacetamide, 6-alkyl-2-hydroxynicotinonitriles are formed.

  4. 4.

    When 4-dimethylaminoamino-3-buten-2-one reacts with methylmagnesium iodide, 3-penten-2-one is formed.

  5. 5.

    The reaction of 4-dimethylamino:3-buten:2-one goes with transfer of reaction center, and, as a result, 4-hydroxy-3-methyl-3-buten-2-otie is formed.

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Literature cited

  1. N. K. Kochetkov, Bull Acad. Sci. USSR, Div. Chem. Sci., 1953, No. 6, 991.

  2. R. Backer, A. Schlesinger, J. Am. Chem. Soc., 68, 2009 (1946).

    Google Scholar 

  3. K. Bowden, E. Braude, E. Jones, B. Weedon, J. Chem. Soc., 1946, 45.

  4. K. Mannich, W. Lammering, Ber., 55, 3510 (1922).

    Google Scholar 

  5. A. F. Plate and T. A. Meerovich, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1940, No. 2, 219.

  6. A. N. Nesmeyanov, N. K. Kochetkov, M. Ya. Karpeisky, and G. V. Aleksandrova, Proc. Acad. Sci. USSR, 82, 409 (1952).

    Google Scholar 

  7. N. K. Kochetkov and G. V. Aleksandrova, Proc. Acad. Sci. USSR, 85, 1033 (1952).

    Google Scholar 

  8. E. Andre, Ann. chim., (8), 29, 513 (1913).

    Google Scholar 

  9. A. N. Nesmeyanov, N. K Kochetkov, and M. 1. Rybinskaya, Bull Acad. Sci. USSR. Div. Chem. Sci., 1950. No. 1, 350.

  10. N. K. Kochetkov, A. N. Nesmeyanov, and N. A. Semenov, Bull. Acad. Sci. USSR. Div. Chem. Sci., 1951, No. 1, 67.

  11. L. Claisen, Ber., 36, 3673 (1903).

    Google Scholar 

  12. N. K. Kochetkov, Proc. Acad. Sci. USSR, 84, 289 (1952).

    Google Scholar 

  13. J. Bardhan, J. Chem. Soc., 1929. 2223.

  14. R. Mariella, J. Am. Chem. Soc., 69, 2670 (1947); 73, 1368 (1951).

    Google Scholar 

  15. M. Julia, Ann. chim., (10), 5, 595 (1950).

    Google Scholar 

  16. A. N. Nesmeyanov, Sci. Mem. Moscow State Univ., 132, 5 (1950).

    Google Scholar 

  17. R. Robinson, J. Chem. Soc., 109, 1038 (1916).

    Google Scholar 

  18. W. Lauer, G. Lones, J. Am. Chem. Soc., 59, 232 (1937).

    Google Scholar 

  19. L. Claisen, Ber., 42, 59 (1909).

    Google Scholar 

  20. K. A uwers, F. Eisenlohr, J. prak. Chem., (2), 82, 124 (1910).

    Google Scholar 

  21. O. Diels, K. Ilberg, Ber., 49, 160 (1916).

    Google Scholar 

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Kochetkov, N.K. 2-Aminovinyl ketones Communication 2. Some reactions of alkyl 2-dialkylaminovinyl ketones. Russ Chem Bull 3, 37–43 (1954). https://doi.org/10.1007/BF01195423

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  • DOI: https://doi.org/10.1007/BF01195423

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