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. (Figure presented.).
Original language | English |
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Pages (from-to) | 4073-4079 |
Number of pages | 7 |
Journal | Advanced Synthesis and Catalysis |
Volume | 360 |
Issue number | 21 |
DOIs | |
Publication status | Published - 2018 Nov 5 |
Bibliographical note
Publisher Copyright:© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords
- 4-Aminopyrroles
- Enamines
- Hantzsch-type one-pot approach
- Kornblum oxidation
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry