Iodine‐Promoted One‐pot Synthesis of Highly Substituted 4‐Aminopyrroles and Bis‐4‐aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines

Abstract

AbstractAn iodine‐promoted one‐pot synthesis of functionally diverse and highly substituted 4‐aminopyrroles directly from aryl methyl ketones, arylamines, and enamines was developed. The reaction involves in‐situ oxidation of aryl methyl ketone to glyoxal, subsequent imine formation by aniline, followed by nucleophilic addition of enamine, and cyclization to afford highly substituted 4‐aminopyrroles. This reaction involved the formation of two C−N bonds and one C−C bond by a formal [1+1+3] annulation approach. The present method provides an interesting framework of two 4‐aminopyrrole units directly attached to a biphenyl core by the reaction of 4,4′‐diacyl biphenyl, amine, and enamine groups. This Hantzsch‐type one‐pot reaction provides diverse 4‐aminopyrroles, which could be useful in medicinal/material chemistry.magnified image