Synthesis of diverse aryl‐substituted amino propanes

Abstract

Amines bearing diverse aryl substituents for potential utilities as energy and new materials have been synthesized from aziridine‐2‐carboxaldehyde and diverse aryl‐containing substrates. At first two aryl groups were to yield (aziridine‐2‐yl)‐1,1‐diaryl‐methane which was converted to 5‐diarylmethyl oxazolidin‐2‐one as a synthetic intermediate. They were further reacted with another aryl group in the presence of methanesulfonic acid to yield 2,3,3‐triarylpropylamine with the possible carbenium ion intermediate. In addition, this reaction with a second additional phenolic aryl group gave rise to the diversely substituted 3‐(4‐methoxyphenyl)‐(2,3‐dihydrobenzofuran‐2‐yl)methanamine derived from the intramolecular aziridine ring‐opening reaction by hydroxy group at phenol.