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.
Abstract:We describe an original pathway to produce new 5-substituted 3-methyl-6-nitrobenzoxazolones by the reaction of aromatic carbonyl and α-carbonyl ester derivatives with a benzoxazolinonic anion formed exclusively via the TDAE strategy.
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