TDAE Strategy in the Benzoxazolone Series: Synthesis and Reactivity of a New Benzoxazolinonic Anion

International audienceWe describe an original pathway to produce new 5-substituted 3-methyl-6-nitro-benzoxazolones by the reaction of aromatic carbonyl and α-carbonyl ester derivatives with a benzoxazolinonic anion formed exclusively via the TDAE strategy

Original TDAE reactivity in benzoxa- and benzothiazolone series

We present herein an extension of the TDAE strategy using original heterocyclic carbaldehyde as electrophiles. We also evaluate the influence of the presence of nitro group on the reactivity. The TDAE-initiated reactions of various halomethyl and gem-dihalomethyl derivatives with nonnitrated carbaldehyde 1 or 2 formed the expected products accompagnied by original rearranged products while the presence of a nitro group just like the carbaldehyde 21 furnished only the expected products in good yields