Nov 2016 - Article in Synlett Published

Olga Bodero's procedure for making 2-aryl-1,4-benzoxazin-3-ones is published

Olga Bodero, Alan C. Spivey 'An Expedient Synthesis of 2-Aryl-1,4-benzoxazin-3-ones via Tandem Anionic Cyclisation/Alkylation Reactions of N-Boc-O-benzyl-2-aminophenols’, Synlett 2016, 28(4), 471-474. DOI: 10.1055/s-0036-1588348

A one-pot, tandem anionic cyclization/alkylation reaction of N-Boc-O-benzylated-2-aminophenols to give 2-aryl-1,4-benzoxazin-3-ones is described. The Boc protecting group plays a crucial role in the process, as the tert-butoxide liberated in the cyclisation step facilitates the benzylic deprotonation necessary for the subsequent alkylation. The reaction gives expedient access to a range of substitution patterns in 1,4-benzoxazin-3-ones of potential biological relevance.