851402-72-7Relevant academic research and scientific papers
6-Spiro-1,4-diazepane-2,5-diones by head-to-tail N1/C2 amide bond formation
Van Berkom, Leon W. A.,De Gelder, Rene,Scheeren, Hans W.
, p. 907 - 917 (2007/10/03)
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.
