Amino acid derived 1,4-dialkyl substituted imidazolones.
A general method for synthesis of 1,4-substituted imidazolones from amino acids on solid support or in solution has been developed. Amino acid derived 3-Boc-(1,3)-oxazinane (Box) protected amino aldehyde building blocks were coupled through urea bonds to the amino terminal of dipeptides or amino acids. Upon acidic release, the aldehyde instantaneously formed the cyclic N-carbamyliminium ion, which rearranged to the corresponding imidazolone. Under strongly acidic conditions the imidazolones acted as nuclophiles in the Pictet-Spengler reaction.
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, Copenhagen DK-2100, Denmark. fdi@farma.ku.dk
Frederik
F
Diness
Morten
M
Meldal
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure
D000596:Amino Acids; D007093:Imidazoles; C117197:imidazolone; D003300:Copper