Synthesis of pyrroles from N-sub stitutedα-amino ketones

  • S. I. Zav'yalov
  • I. F. Mustafaeva
  • N. I. Aronova
  • N. N. Makhova
Organic and Biological Chemistry
  • 30 Downloads

Conclusions

  1. 1.

    The reaction of 2-phenyl-4-acetyl-2-oxazolinone with piperidine and methylamine respectively gave the piperidide of α-benzamidoacetoacetic acid and 2-phenyl-4-(α-methylaminoethylidene)-5-oxazolinone.

     
  2. 2.

    Reaction of the enamines, obtained by the reaction of the K salts of glycine and α-alanine with 2-formylcyclohexanone, with acetic anhydride leads to the formation of l-acetyl-3, 4-tetramethylenepyrrole and its 2-methyl derivative.

     
  3. 3.

    The reaction of piperidinoacetone with benzylamine and piperidine hydrobromide in benzene gives l-benzyl-2-(piperidinomethyl)-4-methylpyrrole.

     
  4. 4.

    The quaternary salt of 3-keto-2, 3,1, 6-tetrahydropyridine is converted to l-benzyl-2, 4-dimethyl-pyrrole under the influence of benzylamine.

     

Keywords

Acetic Benzene Glycine Ketone Anhydride 

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Literature cited

  1. 1.
    J. J. Scott, Biochem. J.,62, 6 (1956).Google Scholar
  2. 2.
    G. Nominé, L. Pénasse, and V. Delaroff, Ann. Pharm. Franc.,16, 436 (1958).Google Scholar
  3. 3.
    Heterocyclic Compounds [Russian translation], Vol. 6, IL (1960), p. 312.Google Scholar
  4. 4.
    S. I. Zav'yalova, N. I. Aronova, and N. N. Makhova, RIMIOS, “Khimiya”,22, 19 (1971).Google Scholar
  5. 5.
    O. Wallach, Ann. Chem.,329, 114 (1903).Google Scholar
  6. 6.
    L. P. Vinogradova, G. A. Kogan, and S. I. Zav'yalov, Izv. Akad. Nauk SSSR, Ser. Khim.,1964, 1054.Google Scholar
  7. 7.
    S. Hauptmann, M. Weifenfels, E. M. Werner, and J. Weisflog, Z. Chem.,9, 22 (1969).Google Scholar
  8. 8.
    S. Attenburrow, D. F. Elliot, and E. F. Penny, J. Chem. Soc.,1948, 310.Google Scholar
  9. 9.
    M. Bockmuhl and G. Ehrhart, Ann. Chem.,561, 52 (1948).Google Scholar
  10. 10.
    É. A. Mistryukov and G. G. Katvalyan, Izv. Akad. Nauk SSSR, Ser. Khim.,1969, 2800.Google Scholar
  11. 11.
    H. Fischer and B. Wallach, Ann. Chen.,447, 41 (1926).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • S. I. Zav'yalov
    • 1
  • I. F. Mustafaeva
    • 1
  • N. I. Aronova
    • 1
  • N. N. Makhova
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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