Skip to main content
SpringerLink
Log in

Acyl iodides in organic synthesis: VIII. Reactions with amino acids

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Reactions of acyl iodides RCOI (R=Me, Ph) with glycine, β-alanine, and γ-aminobutyric acid were investigated. The reaction proceeded easily at room temperature without solvent involving both functional groups H2N and COOH. The prevalence of one of the reaction directions depends on the acidity of the amino acid. The more acidic glycine (pКa 2.4) reacts with RCOI affording mainly N-acylated product, whereas β-alanine (pК a 3.60) and especially γ-aminobutyric acid (pКa 4.06) are predominantly involved into exchange iodination furnishing the corresponding aminoacyl iodides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Zh. Org. Khim., 2002, vol. 38, p. 1630.

    Google Scholar 

  2. Voronkov, M.G. and Shagun, V.A., Zh. Org. Khim., 2003, vol. 39, p. 363.

    Google Scholar 

  3. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Zh. Org. Khim., 2002, vol. 38, p. 1633.

    Google Scholar 

  4. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Zh. Org. Khim., 2004, vol. 40, p. 387.

    Google Scholar 

  5. Voronkov, M.G., Trukhina, A.A., and Vlasova, N.N., Zh. Org. Khim., 2004, vol. 40, p. 498.

    Google Scholar 

  6. Voronkov, M.G., Belousova, L.I., Trukhina, A.A., and Vlasova, N.N., Zh. Org. Khim., 2003, vol. 39, p. 1774.

    Google Scholar 

  7. Ronwin, E., J. Org. Chem., 1953, vol. 18, p. 127.

    CAS  Google Scholar 

  8. Ronwin, E., J. Org. Chem., 1953, vol. 18, p. 1546.

    CAS  Google Scholar 

  9. Teobald, D.W. and Smith, J.C., Chem. Ind., 1958, vol. 32, p. 1007.

    Google Scholar 

  10. Spravochnik khimika (Handbook of Chemist), Nikol’skii, B.P., Ed., Moscow: Khimiya, 1963, vol. 2, p. 398.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    M. G. Voronkov, L. I. Belousova, A. A. Trukhina & N. L. Vlasova

Authors
  1. M. G. Voronkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. I. Belousova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Trukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. L. Vlasova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. G. Voronkov.

Additional information

Original Russian Text © M.G. Voronkov, L.I. Belousova, A.A. Trukhina, N.L. Vlasova, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, no. 2, pp. 189–191.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Voronkov, M.G., Belousova, L.I., Trukhina, A.A. et al. Acyl iodides in organic synthesis: VIII. Reactions with amino acids. Russ J Org Chem 42, 172–174 (2006). https://doi.org/10.1134/S1070428002120023

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428002120023

Keywords

Search

Navigation