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

Hitesh B. Jalani, Jyotirling R. Mali, Hyejun Park, Jae Kyun Lee, Kiho Lee, Kyeong Lee, Yongseok Choi

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 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.

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusAccepted/In press - 2018 Jan 1

Fingerprint

Ketones
Iodine
Glyoxal
Imines
Cyclization
Aniline
Amines
Oxidation
diphenyl
aniline

Keywords

  • 4-Aminopyrroles
  • Enamines
  • Hantzsch-type one-pot approach
  • Kornblum oxidation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Iodine-Promoted One-pot Synthesis of Highly Substituted 4-Aminopyrroles and Bis-4-aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines. / Jalani, Hitesh B.; Mali, Jyotirling R.; Park, Hyejun; Lee, Jae Kyun; Lee, Kiho; Lee, Kyeong; Choi, Yongseok.

In: Advanced Synthesis and Catalysis, 01.01.2018.

Research output: Contribution to journalArticle

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AU - Mali, Jyotirling R.

AU - Park, Hyejun

AU - Lee, Jae Kyun

AU - Lee, Kiho

AU - Lee, Kyeong

AU - Choi, Yongseok

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N2 - 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.

AB - 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.

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