Synthesis of 4-Hydroxy-5-phenylaminoimidazoles through a Three-Component Reaction of Sulfur Ylides, Nitrosobenzenes, and Amidines

A novel annulation reaction of amidines with sulfur ylides and nitrobenzenes has been developed, affording various novel 4-hydroxy-5-phenylaminoimidazoles in moderate to excellent yields. The 4-hydroxy-5-phenylaminoimidazoles have been further converted into α-ketoamide and imidazol-4-imine derivatives. Moreover, a plausible mechanism for this multicomponent reaction is proposed.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-27
DOI
https://doi.org/10.1021/acs.joc.4c02079
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.25

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article

Synthesis of 4-Hydroxy-5-phenylaminoimidazoles through a Three-Component Reaction of Sulfur Ylides, Nitrosobenzenes, and Amidines

Huajian Zhu, Jiaan Shao, Yifeng Hao, Linghui Zeng et al.
1 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.25
article

Synthesis of 4-Hydroxy-5-phenylaminoimidazoles through a Three-Component Reaction of Sulfur Ylides, Nitrosobenzenes, and Amidines

Huajian Zhu, Jiaan Shao, Yifeng Hao, Linghui Zeng, Gongruixue Zeng, Chaowei Xiang, Yunlong Pan, Jiankang Zhang, Chong Zhang
article en
1 citations

Abstract

A novel annulation reaction of amidines with sulfur ylides and nitrobenzenes has been developed, affording various novel 4-hydroxy-5-phenylaminoimidazoles in moderate to excellent yields. The 4-hydroxy-5-phenylaminoimidazoles have been further converted into α-ketoamide and imidazol-4-imine derivatives. Moreover, a plausible mechanism for this multicomponent reaction is proposed.

The Journal of Organic ChemistryVol. 89(24)
Hangzhou City University, Zhejiang University (CN)
Natural Science Foundation of Zhejiang Province
Clean water and sanitation
Openalex Percentile: Top 46%
Sulfur-Based Synthesis Techniques
0.25
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Synthesis of 4-Hydroxy-5-phenylaminoimidazoles through a Three-Component Reaction of Sulfur Ylides, Nitrosobenzenes, and Amidines — Huajian Zhu, Jiaan Shao, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS