Straightforward ring expansion of pyroglutamates to perhydro-1,3-diazepine-2,4-diones.
[reaction: see text] Perhydro-1,3-diazepine-2,4-diones are rare and can only be prepared, up to now, by special methods. A new one-step protocol was developed, comprising N-carbamoylation using an isocyanate followed by intramolecular ring expansion. This new methodology provides a straightforward access to this interesting seven-membered skeleton.
Stevens
Christian V
CV
Research group SynBioC, Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Gent, Belgium. chris.stevens@ugent.be
Dieltiens
Nicolai
N
Claeys
Diederica D
DD
D001381:Azepines / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D017879:Isothiocyanates / Q000737:chemistry; D015394:Molecular Structure; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry*
D001381:Azepines; D017879:Isothiocyanates; C037152:isothiocyanic acid; D011761:Pyrrolidonecarboxylic Acid