Straightforward Ring Expansion of Pyroglutamates to Perhydro-1,3-diazepine-2,4-diones

C.V. Stevens, N. Dieltiens, D.D. Claeys
Organic Letters
7 (6), 1117–1119


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.

(Additions and corrections: Org. Lett., 2005, 7, 5347), 2005