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
N1 - Funding Information:
This work was supported by grants from the National Research Foundation of Korea, Ministry of Science and ICT (2018R1 A5 A2023127) and the Korea Health Technology R & D Project, Ministry of Health & Welfare, Republic of Korea (HI15C0789). We are thankful to Prof. Hongjian Lu of ICBMS, Nanjing University, China for generously providing the enamines used in this study.
PY - 2018/11/5
Y1 - 2018/11/5
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. (Figure presented.).
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. (Figure presented.).
KW - 4-Aminopyrroles
KW - Enamines
KW - Hantzsch-type one-pot approach
KW - Kornblum oxidation
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U2 - 10.1002/adsc.201800899
DO - 10.1002/adsc.201800899
M3 - Article
AN - SCOPUS:85053623083
VL - 360
SP - 4073
EP - 4079
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 21
ER -