N-protected 1,2-oxazetidines as a source of electrophilic oxygen: straightforward access to benzomorpholines and related heterocycles by using a reactive tether

Tomas Javorskis; Simona Sriubaitė; Gintautas Bagdžiūnas; Edvinas Orentas

doi:10.1002/chem.201500731

N-protected 1,2-oxazetidines as a source of electrophilic oxygen: straightforward access to benzomorpholines and related heterocycles by using a reactive tether

Chemistry. 2015 Jun 15;21(25):9157-64. doi: 10.1002/chem.201500731. Epub 2015 May 8.

Authors

Tomas Javorskis¹, Simona Sriubaitė¹, Gintautas Bagdžiūnas², Edvinas Orentas³

Affiliations

¹ Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225, Vilnius (Lithuania).
² Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilėnų pl. 19, 50254 Kaunas (Lithuania).
³ Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225, Vilnius (Lithuania). edvinas.orentas@chf.vu.lt.

PMID: 25959630
DOI: 10.1002/chem.201500731

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.

Keywords: 1,2-oxazetidines; heterocycles; oxygen; radicals; synthesis design.