2- Aza-3-cyano-l,4-quinones

A quite different approach was utilized for the synthesis of 2-aza-3-cyano-l,4-quinones (Scheme 4). Thermal rearrangement of 2,3-bisazido-... 

The observed ring expansion of 2-azido-2-phenylindandione (129) and 2,2-diazido-l,3-indandione (130), along with the established propensity of 2,6-diazido- and 2,5-diazido-l,4-quinones to undergo easy, thermally induced ring contractions to 2-cyano-4-azido-l,3-cyclopentene-diones suggested a unique synthetic route to 2-aza-3-cyano-l,4-quinones (75JA6181). 

---