MeONH₂·HCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonyl o-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones

Abstract

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o-hydroxyacetophenones with methyl sulfoxides via a MeONH₂·HCl-mediated sequential methylenation/ conjugate­ addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.

Key words

chroman-4-ones - o-hydroxyacetophenones - methylenation - methyl sulfoxides - sulfonyl compounds

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