Nonionic superbase-promoted synthesis of oxazoles and pyrroles: facile synthesis of porphyrins and alpha-C-acyl amino acid esters

A nonionic superbase P(MeNCH2CH2)3N catalyzes the reaction of isocyanoacetates with acyl chlorides or acid anhydrides producing oxazoles, which react with HCl-MeOh to generate alpha-C-acyl amino acid esters. The superbase catalyzes the reaction of nitroalkene with isocyanoacetates producing pyrroles, which help synthesize porphyrins. Strong basicity and nucleophilicity of the superbase make the base as an efficient nonionic deprotonating agent, and the deprotonation occurs even at low temperatures.