A Convenient Access to Functionalized Oxazol-2-One-5-Carboxylates from β-Aminoalcohols Through NBS-Light Mediated Oxidation of Cis- or Trans-N-Alkyloxazolidinones

Abstract

An efficient methodology is developed involving a metal-free oxidation of cis or trans-trisubstituted oxazolidin-2-ones in the presence of NBS under light irradiation for the synthesis of N-alkyl oxazol-2-one-5-carboxylates. The mild conditions employed enable the efficient and rapid synthesis of a variety of those compounds in satisfactory yields.

A simple and general synthetic route to N-alkylazetidines from 1,2-amino alcohols

“…In our previous work, we reported on the transformation of erythro-1,2-amino alcohols 1 into a range of nitrogen heterocyclic compounds including 1,4-oxazin-2-ones, aziridine-2-carboxylates, 1,3-oxazolidin-2-ones, functionalized cyclic sulfamidates and oxazol-2-one-5-carboxylates. 41 These successful results motivated us to further explore the potential of compounds 1 to yield other types of azaheterocycles. Amino alcohols 1 were prepared, through controlled ring opening of ethyl trans--phenylglycidate with amines, as described previously.…”