N-protected 1,2-oxazetidines as a source of electrophilic oxygen: straightforward access to benzomorpholines and
Tomas Javorskis1, Simona Sriubaitė1, Gintautas Bagdžiūnas2
1Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225, Vilnius (Lithuania).
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.
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