A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2H-1-benzopyran-2-ones

Abstract

Halogen acid-catalysed deprotection and cyclisation of Baylis-Hillman products obtained using O-benzylated salicylaldehyde precursors has been shown to afford 3-(halomethyl)coumarins (3-halomethyl-2H-1-benzopyran-2-ones) chemoselectively and in good yield.

heterocycles - synthesis - coumarins - 2H-1-benzopyran-2-ones - Baylis-Hillman reaction

References

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Athough an allylic displacement (S_N′) pathway cannot be excluded, there are some precedents for the addition-elimination sequence outlined in Scheme [2] . See Ref. [15] for further comment.