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Metal/catalyst-free sequential C-N bond forming cascades at room temperature: environment-friendly one-pot synthesis of 5-aminoimidazoles from aryl glyoxals, anilines, and amidines

Authors
Jalani, Hitesh B.Sivaraman, AneeshMin, Kyoung HoLee, Hwa YoungOh, Na KyoungKang, HyeseulKeum, GyochangChoi, YongseokLee, Kyeong
Issue Date
Aug-2022
Publisher
ROYAL SOC CHEMISTRY
Citation
GREEN CHEMISTRY, v.24, no.17, pp 6501 - 6510
Pages
10
Indexed
SCIE
SCOPUS
Journal Title
GREEN CHEMISTRY
Volume
24
Number
17
Start Page
6501
End Page
6510
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/143598
DOI
10.1039/d2gc01407f
ISSN
1463-9262
1463-9270
Abstract
An expeditious one-pot method for the synthesis of highly substituted 5-aminoimidazoles from glyoxals, anilines, and amidines was evaluated under metal/catalyst-free conditions operative at room temperature. The present protocol constitutes an environmentally friendly approach for the synthesis of highly substituted 5-aminoimidazoles, which are important building blocks of several bioactive and medicinal compounds. The readily and commercially available starting materials can be quickly assembled into imidazoles using this protocol and scaling up this process does not require chromatographic purification. Additionally, the reaction of 5-aminoimidazole with 2-bromobenzoyl chloride can provide a novel imidazo[5,1-b]quinazolin-9(4H)-one, thus showcasing the applicability of this protocol.
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