124573-86-0Relevant 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.
Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells
Deng, Jiajie,Guo, Guiling,Wu, Xueting,Yu, Zhipeng,Zhao, Xiaohu
supporting information, p. 5602 - 5607 (2020/08/21)
A photo-induced 1,3-dipolar cycloaddition between nitrile imine and highly ring-strained NN double bond as a dipolarophile was discovered. The photo-isomerization of carbon-bridged octocyclic azobenzene (CBOA) into its trans-configuration accelerates the ligation reaction at a very rapid rate (28 400 M-1 s-1). The CBOA-based photo-click reaction was proved to be bioorthogonal. In addition, the NoxaB peptide was successfully cross-linked by a CBOA stapler which plays a dual role: Photo-control of the conformation of the peptide and photo-conjugation of probes in live cells.
An easy direct arylation of 3-arylsydnones
Yang, Yiwen,Gong, Hao,Kuang, Chunxiang
supporting information, p. 1469 - 1474 (2013/06/27)
An easy one-step synthesis of 3,4-diarylsydnones from 3-arylsydnones and arylboronic acids by Pd-catalyzed C-H bond activation is described. Georg Thieme Verlag Stuttgart New York.
Synthesis of Some New 3,4-Diarylsydnones
Csongar, Ch.,Mueller, I.,Slezak, H.,Klebsch, H.-J.,Tomaschewski, G.
, p. 1006 - 1014 (2007/10/02)
The synthesis of some new sydnones 4 is described.Their characteristic absorption maxima, mass spectroscopic fragmentation and C=O-valence vibrations are given.The sydnones 4 are synthezid by nitrosation of C,N-diarylglycines 3 (from strecker synthesis) a
