Synthesis of 2,4-diketo-5-phenyl-.DELTA.5-7oxa-1,3-diazabicyclo[4.4.0]decane and 2,4-diketo-3-phenyl-.DELTA.5-7-oxa-1,5-diazabicyclo[4.4.0]decane

Abstract

nium) cobalt (II) decachloride hydrate, 35616-92-3; dipyridinium 1,1'-[ethylenebis (thioethylene) [diperchlorate, 35624-16-9; V-[3,6-bis(thia)-7-octenyl]pyridinium perchlorate, 35624-17-0; dipyridinium , '-ethylenediperchlorate, 6601-41-8. Acknowledgments.-Funds for this work were provided by ARPA and by a Du Pont Young Faculty Grant. The author is grateful to Dr. Ernst Habicht, Jr., for originally bringing the disulfonium ion to his attention, as well as to Dr.

Chemistry of Bridged Lactams and Related Heterocycles

“…Toshimitsu reported the use of intramolecular amidoselenation reaction toward the synthesis of bridged lactams; however, the originally assigned bridged structure 254 was later found to be incorrect (Scheme ). , A similar tendency of amides to cyclize via an oxygen atom rather than a nitrogen atom was also described by Smissman and co-workers in the context of their work on bridged barbituric acid derivatives (see section 6.2.2). − …”

“…In a 1964 report, in analogy to known drugs containing planar imide bonds, Smissman proposed bridged bicyclic imides 307 – 310 as potential anticonvulsant agents (Figure ) . However, over the next 20 years, Smissman and co-workers found that synthesis of the proposed bridged imides 307 – 310 was more difficult than initially expected. − Attempts to prepare bridged barbituric acids, bridged amides, or bridged imides via intramolecular alkylation approaches (Scheme ) − or via intramolecular condensation methods (Scheme ) were unsuccessful due to the propensity of the tested precursors to react with electrophiles at the oxygen rather than nitrogen atom. Moreover, Smissman found that structures of bridged imides reported in the literature by other groups were incorrect (Scheme ). , …”