Synthesis of novel 2-alkyl and 2-aryl 4-phosphorylated oxazolines from dimethyl (±)-phosphoserinate

Abstract

Herein, we report the synthesis of novel 2-alkyl and 2-aryl substituted 4-phosphorylated oxazolines. The synthesis involves a one-pot cyclization reaction between dimethyl (±)-phosphoserinate and several imidate derivatives, prepared under Pinner reaction conditions. This approach produced 2-phenyl and 2-(p-methoxyphenyl) phosphorylated oxazolines and 2-alkyl substituted oxazolines, including a cyclopropyl derivative in good yields. Oxidation of the 2-phenyl phosphorylated oxazoline using DDQ led to the formation of the corresponding phosphorylated oxazole. This method can be easily extended to a wide variety of imidates with different substituents and also offers a practical and versatile approach for advancing research in azaheterocyclic phosphonates.