Tin (IV) Chloride-promoted Reactions of a-Hydroxy Nitriles with b-Dicarbonyl Compounds Synthesis of 4-Amino-2,5-dihydro-2-furanones and Their Conversion into Tetronic Acid Derivatives

Abstract

β-Keto esters and β-diesters react with α-hydroxy nitriles in the presence of stoichiometric amounts of tin(IV) chloride to give 3-acyl-4-amino-2(5H)-furanones(2) and ethyl 4-amino-2,5-dihydro-2-oxofuran-3-carboxylates (3). The acyldihydrofuranones (2) can be converted into acyltetronic acid derivatives (6) while the ethyl furan-3-carboxylates (3) can be converted into tetronic acids (8)