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

Title
Iodine-Promoted One-pot Synthesis of Highly Substituted 4-Aminopyrroles and Bis-4-aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines
Authors
이재균Hitesh B. JalaniaJyotirling R. Malib박혜준이기호이경최용석
Keywords
one-pot synthesis; X-ray single crystal structure; [1+1+3] annulation approach.; medicinal/material chemistry.
Issue Date
2018-11
Publisher
Advanced synthesis & catalysis
Citation
VOL 360, NO 21-4079
Abstract
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 CN bonds and one CC 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.
URI
http://pubs.kist.re.kr/handle/201004/68492
ISSN
1615-4150
Appears in Collections:
KIST Publication > Article
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