Synthesis of Isomeric Aminomethyl Derivatives of Furylmethanephosphonates

Abstract

By chloromethylation of diethyl 2- and 3-furylmethanephosphonates 5-chloromethylfur-2(3)-ylmethanephosphonates were synthesized. The other four isomers of chloromethyl derivatives of furylmethanephosphonates were prepared by substitution of hydroxy groups in the corresponding phosphorylated furylmethanols via the reaction with thionyl chloride in the presence of pyridine. Thermal stability of these chlorides was sufficiently high, and they were involved in nucleophilic substitution of chlorine with azido group by treating with sodium azide in boiling acetonitrile in the presence of potassium iodide. No decomposition of substrates was observed. The azides obtained were reduced to amines with triphenylphosphine in ethanol.