One-pot synthesis of a new class of alkynyl anionic synthons: the 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones

Abstract

An efficient approach for the synthesis of a new class of anionic synthons: the 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones employing a one-pot three-component reaction is reported. Reaction of trimethylsilylacetylene, o-iodophenol and nine different bromomethylcoumarins in THF solvent at 80 °C under sealed tube conditions gave nine novel 4-(2',2-trimethylsilylethynylphenoxymethyl)-2H-chromen-2-ones in greater than 90% isolated yields. All compounds were spectroscopically characterized by elemental analysis, FT-IR, MS, ¹H-, and ¹³C-NMR techniques.