Piperazine-2,3,5-triones in the synthesis of constrained peptides

Patrick D. Bailey, Andrew N. Boa, S. Richard Baker, Joanne Clayson, Ernest J. Murray, Georgina M. Rosair

Research output: Contribution to journalArticle

4 Citations (Scopus)


Amino acid amides react with diethyl oxalate and sodium ethoxide to yield 6-substituted piperazine-2,3,5-triones, which can be mono-alkylated at N4, bis-alkylated at N4 and C6, or tris-alkylated at N4, N1, and C6 under mild basic conditions; this provides access to i) a,a-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(a)-N bond formation; iii) DKP analogues.

Original languageEnglish
Pages (from-to)7557-7560
Number of pages4
JournalTetrahedron Letters
Issue number42
Publication statusPublished - 15 Oct 1999


  • Amino acids and derivatives
  • Peptide analogues/mimetics
  • Piperazines/piperazinones

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    Bailey, P. D., Boa, A. N., Baker, S. R., Clayson, J., Murray, E. J., & Rosair, G. M. (1999). Piperazine-2,3,5-triones in the synthesis of constrained peptides. Tetrahedron Letters, 40(42), 7557-7560. https://doi.org/10.1016/S0040-4039(99)01602-0