Premium
6‐Spiro‐1,4‐diazepane‐2,5‐diones by Head‐to‐Tail N1/C2 Amide Bond Formation
Author(s) -
Van Berkom Leon W. A.,
de Gelder René,
Scheeren Hans W.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400782
Subject(s) - chemistry , amide , peptide bond , dipeptide , ring (chemistry) , moiety , stereochemistry , amine gas treating , peptide , organic chemistry , biochemistry
The synthesis of a series of 6‐spiro‐1,4‐diazepane‐2,5‐diones containing an arylpropylamide moiety via head‐to‐tail cyclisation of a terminal amine and a terminal carboxylate ester is described. To induce ring closure of the dipeptide precursor, both lactamisation of the N4/C5 amide bond and N1/C2 amide bond were investigated. Whereas ring closure of the N4/C5 amide bond proved unsuccessful, ring closure of the N1/C2 amide bond was more viable. Furthermore, it was discovered that incorporation of a N , N ‐disubstituted amide bond in the peptide sequence was essential for cyclisation to occur. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)