Citation: Yanhui Guo, Yunyun Liu, Jie-Ping Wan. Amine-catalyzed synthesis of N²-sulfonyl 1, 2, 3-triazole in water and the tunable N²-H 1, 2, 3-triazole synthesis in DMSO via metal-free enamine annulation[J]. Chinese Chemical Letters, ;2022, 33(2): 855-858. doi: 10.1016/j.cclet.2021.08.003 shu

Amine-catalyzed synthesis of N²-sulfonyl 1, 2, 3-triazole in water and the tunable N²-H 1, 2, 3-triazole synthesis in DMSO via metal-free enamine annulation

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China

wanjieping@jxnu.edu.cn

Received Date: 30 May 2021
Revised Date: 30 July 2021
Accepted Date: 2 August 2021
Available Online: 8 August 2021

Figures(5)

The selective synthesis of N²-sulfonyl and N²-H 1, 2, 3-triazoles via organocatalytic annulation of enaminone/enaminoester with sulfonyl azide has been realized. The unconventional selectivity providing N²-sulfoyl 1, 2, 3-triazoles takes place in pure water, wherein the hydrogen bond effect between water and the intermediate resulting from enamine-azide corporation accounts for the novel reaction selectivity. On the other hand, the reactions conducted in DMSO specifically afford N²-H 1, 2, 3-triazoles in the absence of such hydrogen bond effect.
- Enaminone,
- Annulation,
- N²-sulfonyl 1, 2, 3-triazole,
- Selectivity,
- Green synthesis,
- Sulfonyl azide
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沈阳化工大学材料科学与工程学院沈阳 110142

Amine-catalyzed synthesis of N2-sulfonyl 1, 2, 3-triazole in water and the tunable N2-H 1, 2, 3-triazole synthesis in DMSO via metal-free enamine annulation

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通讯作者: 陈斌, bchen63@163.com

Amine-catalyzed synthesis of N²-sulfonyl 1, 2, 3-triazole in water and the tunable N²-H 1, 2, 3-triazole synthesis in DMSO via metal-free enamine annulation