4266-86-8Relevant academic research and scientific papers
Water-Involved Ring-Opening of 4-Phenyl-1,2,4-triazoline-3,5-dione for “Photo-Clicked” Access to Carbamoyl Formazan Photoswitches In Situ
Zheng, Yuanqin,Zhou, Yuqiao,Zhang, Yan,Deng, Pengchi,Zhao, Xiaohu,Jiang, Shichao,Du, Guangxi,Shen, Xin,Xie, Xinyu,Su, Zhishan,Yu, Zhipeng
, (2021/12/22)
Cyclic azodicarbonyl derivatives, particularly 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), commonly serve as arenophile, dienophile, enophile and electrophile. Perplexed by its instability in aqueous environment, there are few studies focused on the transient intermediate produced by hydrolysis of PTAD to achieve synthetic significance. Herein, we describe a “photo-click” method that involves nitrile imine (NI) from diarylsydnone to capture the diazenecarbonyl-phenyl-carbamic acid (DACPA) generated by water-promoted ring-opening of PTAD. DFT calculation reveal that H-bonding interactions between PTAD and water are vital to form DACPA which exhibited an umpolung effect during ligation by nature bond orbit (NBO) analysis. The ultra-fast ligation resulted in carbamoyl formazans, as a unique Z?E photo-switchable linker on target molecules, including peptide and drugs, with excellent anti-fatigue performance. This strategy is showcased to construct highly functionalized carbamoyl formazans in situ for photo-pharmacology and material studies, which also expands the chemistry of PTAD in aqueous media.
Photo-accelerated "click" reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation
Zhang, Xiaocui,Wu, Xueting,Jiang, Shichao,Gao, Jingshuo,Yao, Zhuojun,Deng, Jiajie,Zhang, Linmeng,Yu, Zhipeng
supporting information, p. 7187 - 7190 (2019/07/02)
We constructed a library of diarylsydnone (DASyd) candidates in search of a photoclickable reaction toward alkynes, enabling an ultra-accelerated reactivity, while suppressing the background cycloaddition in the dark. The in vitro and in vivo protein labe
Synthesis of 2 H-indazoles by the [3 + 2] dipolar cycloaddition of sydnones with arynes
Fang, Yuesi,Wu, Chunrui,Larock, Richard C.,Shi, Feng
experimental part, p. 8840 - 8851 (2012/01/02)
A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields using this protocol, and subsequent Pd-catalyzed coupl
Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones
Wu, Chunrui,Fang, Yuesi,Larock, Richard C.,Shi, Feng
supporting information; experimental part, p. 2234 - 2237 (2010/08/04)
A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.
