1400663-74-2Relevant academic research and scientific papers
Preparation method of 2-aryl benzotriazole compound
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Paragraph 0057-0064, (2020/05/14)
The invention relates to a synthesis method of a 2-aryl benzotriazole compound. In an organic solvent, under a nitrogen condition, an o-phenylenediamine compound with a structure shown as a formula (I) in the structural formula and an aryl nitrogen source with a structure shown as a formula (II) in the structural formula are used as reaction substrates to be successively subjected to intermolecular N-N coupling and intramolecular N-N bond coupling condensation by using a cheap copper-containing catalyst in a strong alkali environment so as to obtain a 2-aryl benzotriazole compound. According to the method, o-phenylenediamine and nitrobenzene raw materials are commercialized, cheap and easily available, the reaction substrate range is wide, the functional group tolerance is good, the reaction conditions are simple, the yield and purity of the product are high, a new synthesis route and a method are developed for the 2-aryl benzotriazole compound, and the method has good application potential and research value.
Cu(I)/KOH-Promoted Condensation between o-Arylenediamines and Nitroarenes to Access 2-Aryl-2H-Benzotriazoles
Li, Hong-Chen,Gao, Wen-Xia,Huang, Xiao-Bo,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
supporting information, p. 2847 - 2851 (2020/06/02)
Reported is the condensation between o-arylenediamines and nitroarenes enabled by a cooperative action of acid and base, providing a direct entry to 2-aryl-2H-benzotriazoles. The potential practicability of this methodology was demonstrated by 100 mmol-scale reactions and the synthesis of serotonin/dopamine receptor ligand and human growth hormone. (Figure presented.).
Reactivity-based detection of copper(II) ion in water: Oxidative cyclization of azoaromatics as fluorescence turn-on signaling mechanism
Jo, Junyong,Lee, Ho Yong,Liu, Wenjun,Olasz, Andras,Chen, Chun-Hsing,Lee, Dongwhan
, p. 16000 - 16007 (2012/10/30)
An oxidative cyclization reaction transforms nonemissive azoanilines into highly fluorescent benzotriazoles. We have found that introduction of multiple electron-donating amino groups onto a simple o-(phenylazo)aniline platform dramatically accelerates its conversion to the emissive polycyclic product. Notably, this chemistry can be effected by μM-level concentrations of copper(II) ion in water (pH = 6-8) at room temperature to elicit >80-fold enhancement in the green emission at λem = 530 nm. Comparative kinetic and electrochemical studies on a series of structural analogues have established that the accelerated reaction rates correlate directly with a systematic cathodic shift in the oxidation onset potential of the azo precursors. In addition, single-crystal X-ray crystallographic analysis on the most reactive derivative revealed the presence of a five-membered ring intramolecular hydrogen-bonding network. An enhanced contribution of the quinoid-type resonance in such conformation apparently facilitates the mechanistically required proton transfer step, which, in conjunction with electron transfer at lower oxidation potential, contributes to a rapid cyclization reaction triggered by copper(II) ion in water.
