Synthesis of 1,2,4-Trisubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Aromatization Reaction

doi:10.6023/cjoc202306022

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 525-532.DOI: 10.6023/cjoc202306022 Previous Articles Next Articles

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利用串联的Staudinger/aza-Wittig/芳构化反应合成1,2,4-三取代咪唑衍生物

解海^*(), 张雅丽, 秦秀婷, 谷永新^*()

山西大同大学化学与化工学院化学传感山西省重点实验室山西大同 037009

收稿日期:2023-06-26 修回日期:2023-09-25 发布日期:2023-11-07
基金资助:
大同市应用基础研究项目基金(02030710)

Synthesis of 1,2,4-Trisubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Aromatization Reaction

Hai Xie(), Yali Zhang, Xiuting Qin, Yongxin Gu()

College of Chemistry and Chemical Engineering, Shanxi Provincial Key Laboratory of Chemical Biosensing, Shanxi Datong University, Datong, Shanxi 037009

Received:2023-06-26 Revised:2023-09-25 Published:2023-11-07
Contact: * xiehai10@126.com; guyongxin515@126.com
Supported by:
Datong Applied Basic Research Project Fund(02030710)

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Abstract

An efficient and convenient route for the synthesis of 1,2,4-trisubstituted imidazole derivatives was described. Benzamide derivatives containing alkenylazide as the basic raw materials were treated with triphenyl phosphorus, and subsequently 1,2,4-trisubstituted imidazole derivatives were synthesized by a sequential Staudinger/aza-Wittig/aromatization reaction. The reaction is characterized by cheap and easy to obtain starting materials, mild reaction conditions, metal-free catalysts, and simple operation. It is an ideal and efficient synthesis strategy of 1,2,4-trisubstituted imidazole heterocyclic compounds.

Key words: Staudinger reaction, aza-Wittig reaction, aromatization reaction, 1,2,4-trisubstituted imidazole

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Hai Xie, Yali Zhang, Xiuting Qin, Yongxin Gu. Synthesis of 1,2,4-Trisubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Aromatization Reaction[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 525-532.

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Compd.	R¹	R²	R³	Yield^a/%
3a	C₆H₅	C₆H₅	C₆H₅	88
3b	C₆H₅	C₆H₅	4-MeC₆H₄	84
3c	C₆H₅	C₆H₅	4-ClC₆H₄	89
3d	C₆H₅	C₆H₅	4-BrC₆H₄	81
3e	C₆H₅	C₆H₅	4-FC₆H₄	90
3f	C₆H₅	C₆H₅	4-NO₂C₆H₄	80
3g	C₆H₅	4-ClC₆H₄	C₆H₅	86
3h	C₆H₅	4-MeC₆H₄	C₆H₅	85
3i	C₆H₅	2-ClC₆H₄	C₆H₅	84
3j	C₆H₅	4-ClC₆H₄	4-MeOC₆H₄	83
3k	C₆H₅	2-Furyl	C₆H₅	80
3l	4-FC₆H₄	C₆H₅	4-MeC₆H₄	86
3m	Me	C₆H₅	C₆H₅	79

Compd.	R¹	R²	R³	Yield^a/%
3a	C₆H₅	C₆H₅	C₆H₅	88
3b	C₆H₅	C₆H₅	4-MeC₆H₄	84
3c	C₆H₅	C₆H₅	4-ClC₆H₄	89
3d	C₆H₅	C₆H₅	4-BrC₆H₄	81
3e	C₆H₅	C₆H₅	4-FC₆H₄	90
3f	C₆H₅	C₆H₅	4-NO₂C₆H₄	80
3g	C₆H₅	4-ClC₆H₄	C₆H₅	86
3h	C₆H₅	4-MeC₆H₄	C₆H₅	85
3i	C₆H₅	2-ClC₆H₄	C₆H₅	84
3j	C₆H₅	4-ClC₆H₄	4-MeOC₆H₄	83
3k	C₆H₅	2-Furyl	C₆H₅	80
3l	4-FC₆H₄	C₆H₅	4-MeC₆H₄	86
3m	Me	C₆H₅	C₆H₅	79

利用串联的Staudinger/aza-Wittig/芳构化反应合成1,2,4-三取代咪唑衍生物

Synthesis of 1,2,4-Trisubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Aromatization Reaction

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