74877-19-3Relevant articles and documents
Synthesis of 2,4-Diazabicyclooctane-3,7-diones and 3-Thioxo-2,4-diazabicyclooctan-7-one by an Intramolecular Michael-type Reaction. Stability of 2,4 Diaza-, 4-Oxa-2-aza-, and 4-Thia-2-aza-bicyclooctane-3,7-diones
Harris, C. John
, p. 2497 - 2502 (2007/10/02)
Novel 2,4-diazabicyclooctane-3,7-diones (10) have been prepared by an intramolecular Micael-type cyclisation.The analogous 3-thioxo-2,4-diazabicyclooctan-7-one system (20) is obtained by base-catalysed retro-Michael reaction of the less stable 3-arylimino-2-thia-4-azabicyclooctan-7-one isomer (19).The 2-aza-4-oxabicyclooctane-3,7-dione system (17) is shown to be very unstable to base, fragmenting via the carbamic acid to give carbon dioxide and a 4-N-substituted cyclopent-2-enone (11).The relative stability to base of these bicyclic systems is correlated with their structure.
