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 language | English |
|---|---|
| Journal | Advanced Synthesis and Catalysis |
| DOIs | |
| Publication status | Accepted/In press - 2018 Jan 1 |
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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 journal › Article
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TY - JOUR
T1 - Iodine-Promoted One-pot Synthesis of Highly Substituted 4-Aminopyrroles and Bis-4-aminopyrrole from Aryl Methyl Ketones, Arylamines, and Enamines
AU - Jalani, Hitesh B.
AU - Mali, Jyotirling R.
AU - Park, Hyejun
AU - Lee, Jae Kyun
AU - Lee, Kiho
AU - Lee, Kyeong
AU - Choi, Yongseok
PY - 2018/1/1
Y1 - 2018/1/1
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.
KW - 4-Aminopyrroles
KW - Enamines
KW - Hantzsch-type one-pot approach
KW - Kornblum oxidation
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UR - http://www.scopus.com/inward/citedby.url?scp=85053623083&partnerID=8YFLogxK
U2 - 10.1002/adsc.201800899
DO - 10.1002/adsc.201800899
M3 - Article
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
ER -