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Iodine‐Promoted One‐pot Synthesis of Highly Substituted 4‐Aminopyrroles and Bis‐4‐aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines
Author(s) -
Jalani Hitesh B.,
Mali Jyotirling R.,
Park Hyejun,
Lee Jae Kyun,
Lee Kiho,
Lee Kyeong,
Choi Yongseok
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800899
Subject(s) - chemistry , enamine , aryl , imine , annulation , ketone , aniline , glyoxal , organic chemistry , methyl ketone , nucleophilic addition , medicinal chemistry , iodine , catalysis , alkyl
An 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.