DABCO-Assisted Coupling of Some Activated Olefins and 2,3-Dihalo-1,4-naphthoquinones and Conversion to the Anthraquinone Derivatives

Abstract

A new synthesis of mono- and di-α-vinylnaphthoquinones based on stepwise or one-pot substitution of the halogens in 2,3-dihalo-1,4-naphthoquinones by DABCO-assisted enolate ion is described. Di-α-vinylnaphthoquinones undergo thermal 6π electrocyclization to yield 1,4-disubstituted anthraquinones readily.

Baylis-Hillman reaction - DABCO - 2,3-dihalo-1,4-naphthoquinone - activated olefin - anthraquinone

References

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