An Efficient One-Pot Two-Step Three-Component Process for the Synthesis of Trifluoromethylated Hydrochromenes

Abstract

A one-pot two-step three-component process for the synthesis of trifluoromethylated 2-hydroxy-5-oxo-3,4,5,6,7,8-hexahydro-2H-chromenes has been developed. The three-component reaction of dimedone, substituted benzaldehydes, and methyl 4,4,4-trifluorobut-2-ynoate gave the desired products in moderate to good yields. Excellent regioselectivity and diastereoselectivity were observed. Furthermore, refluxing the product chromenes with p-toluenesulfonic acid in toluene gave the corresponding dehydrated products – trifluoromethylated 5-oxo-5,6,7,8-tetrahydro-4H-chromenes.

Key words

hexahydro-2H-chromene - tetrahydro-4H-chromene - 4,4,4-trifluorobut-2-ynoate - multicomponent reaction - one-pot synthesis

• References

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