Condensation of 2-hydroxyacetophenones with trichloroacetonitrile as a route to 2-trichloromethylchromones and 4-hydroxycoumarins

Article abstract of DOI:10.1007/BF02494778

Condensation of 2-hydroxyacetophenones with trichloroacetonitrile in the presence of N-methylanilinomagnesium bromide affords hydroxyaryl β-amino-β-trichloromethylvinyl ketones, which are converted into 2-trichloromethylchromones upon treatment with concentrated HCl. The resulting compounds react with alcoholic solutions of NH₃ or KOH to form 3-amino-1-(2-hydroxyaryl)-4,4,4-trichlorobut-2-en-1-ones and 4-hydroxycoumarins, respectively.