title: N-protected 1,2-oxazetidines as a source of electrophilic oxygen: straightforward access to benzomorpholines and related heterocycles by using a reactive tether.
abstract: A hitherto unknown reactivity of a strained four-membered heterocycle, 1,2-oxazetidine, is reported. When reacted with organometallic compounds, this reagent provides electrophilic oxygen with a nitrogen-terminated two-carbon-atom tether. The synthetic versatility of the products obtained was demonstrated in various transformations, leading to efficient synthesis of six-, seven-, and eight-membered heterocyclic systems of pharmaceutical importance.
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225, Vilnius (Lithuania).
authors.forename: Tomas
authors.initials: T
authors.lastname: Javorskis
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225, Vilnius (Lithuania).
authors.forename: Simona
authors.initials: S
authors.lastname: Sriubaitė
authors.affiliation: Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilėnų pl. 19, 50254 Kaunas (Lithuania).
authors.forename: Gintautas
authors.initials: G
authors.lastname: Bagdžiūnas
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225, Vilnius (Lithuania). edvinas.orentas@chf.vu.lt.
authors.forename: Edvinas
authors.initials: E
authors.lastname: Orentas
keywords: 1,2-oxazetidines; heterocycles; oxygen; radicals; synthesis design