The Synthesis of 2,4-Diketo-5-phenyl-δ5-7-oxa-1,3-diazabicyclo[4.4.0]decane and 2,4-Diketo-3-phenyl-δ5-7-oxa-1,5-diazabicyclo[4.4.0]decane

Edward E. Smissman, James W. Ayres, Peter J. Wirth, Darrell R. Abernethy

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


In an attempt to secure 5-phenyl bioyclo barbiturates, N-(haloalkyl)-5-phenylbarbituric acids were prepared and converted to their corresponding thallous salts. Nitrourea and alkanolamines were allowed to react to produce N-(hydroxyalkyl)ureas, which were converted to the corresponding N-(hydroxyalkyl)-5-phenylbarbituric acids and via these alcohols to the halides. When cyclization of the thallous salts of the N-(halopropyl)-5-phenylbarbituric acids was attempted in benzene-water, no intramolecular C-alkylation occurred and the only product isolated was 2,4-diketo-3-phenyl-δ5-7-oxa-1,5-diazabicyclo[4.4.0]decane. Utilizing anhydrous benzene as the solvent for the cyclization reaction, the product obtained was 2,4-diketo-5-phenyl-δ5-7-oxa-1,3-diazabicyclo-[4.4.0] decane.

Original languageEnglish (US)
Pages (from-to)3486-3488
Number of pages3
JournalJournal of Organic Chemistry
Issue number22
StatePublished - Nov 1 1972

ASJC Scopus subject areas

  • Organic Chemistry


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