Functionalization of Chromones through an Aza-Baylis–Hillman-Type Reaction

Abstract

The synthesis of (N,N′-bisalkoxycarbonyl)hydrazinochromones via the aza-Baylis–Hillman reaction of formylchromones and azodicarboxylates is reported. A plausible mechanistic scheme for the formation of these compounds, involving the chromone formyl group elimination, is proposed. Conformational analysis was performed by DFT calculations. The structure of one example was confirmed by XRD investigation. Full assignment of all ¹H and ¹³C NMR chemical shifts has been unambiguously achieved.

Key words

azodicarboxylates - formylchromones - DABCO - aza-Baylis–Hillman reaction

• References

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