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

Authors
Bailey, PD Boa, AN Baker, SR Clayson, J Murray, EJ Rosair, GM
Citation
Pd. Bailey et al., Piperazine-2,3,5-triones in the synthesis of constrained peptides, TETRAHEDR L, 40(42), 1999, pp. 7557-7560
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
42
Year of publication
1999
Pages
7557 - 7560
Database
ISI
SICI code
0040-4039(19991015)40:42<7557:PITSOC>2.0.ZU;2-X
Abstract
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 N-4, bis-alkylated at N-4 and C-6, or tris-alkylated at N-4, N-1, and C-6 under mild basic conditions; this provides access to i) alpha,alpha-disubstituted cyclic peptide derivatives; ii) constrained peptides via C(alpha)-N bond f ormation; iii) DKP analogues. (C) 1999 Elsevier Science Ltd. All rights res erved.