Synthesis of a Novel Pyrrole Family as Potential Anti-Cancer Agents

Abstract

A one-step selective reaction was developed to synthesize a novel pyrrole family (20 different members) from a keto-epoxide and several aromatic amines at room temperature in 3h. When substituting aromatic amine with aliphatic amines or inorganic bases, furan derivatives were produced selectively. The kinetic behavior of the reactions and structure of the products were characterized by nuclear magnetic resonance spectroscopy. The results showed that our reaction is selective with high yields (> 85%). To understand the selective formation of pyrrole and furan, we conducted computational experiences to study the mechanisms of the primary reaction and its competitor using Density Functional Theory with B3LYP methods and LACVP basis set. Our main contribution was to develop a simple yet selective reaction to synthesize pyrrole derivatives with a strong potential for pharmaceutical application.