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

Hitesh B. Jalani, Aneesh Sivaraman, Kyoung ho Min, Hwa Young Lee, Na Kyoung Oh, Hyeseul Kang, Gyochang Keum, Yongseok Choi, Kyeong Lee

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

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.

Original languageEnglish
Pages (from-to)6501-6510
Number of pages10
JournalGreen Chemistry
Volume24
Issue number17
DOIs
Publication statusPublished - 2022 Jul 22

Bibliographical note

Funding Information:
This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIT) (NRF 2018R1A5A2023127), and the BK21 FOUR Team and Integrated Research Institute for Drug Development, College of Pharmacy, Dongguk University-Seoul, Goyang, 10326, Republic of Korea.

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

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