4340-77-6Relevant articles and documents
Hydrogen peroxide based oxidation of hydrazines using HBr catalyst
Du, Wanting,Ma, Zichao,Shao, Liming,Wang, Jian
, (2021/11/18)
Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.
Synthesis of Unsymmetrical Azoxyarenes via Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling of Anilines with Nitrosoarenes
Shi, Chongyang,Xu, Boxia,Fang, Xiaolan,Yu, Xiaochun,Jin, Huile,Wang, Shun
supporting information, p. 1963 - 1967 (2021/03/04)
A copper-catalyzed oxidative dehydrogenative coupling of nitrosobenzenes with anilines for the synthesis of unsymmetrical azoxybenzenes was developed. This approach uses O2 as the oxidant. The reaction products are diverse unsymmetrical azoxybe
Photosensitive and Photoswitchable TRPA1 Agonists Optically Control Pain through Channel Desensitization
Luo, Jiajie,Qi, Hang,Qiao, Zhen,Tang, Xiaowen,Tang, Yi-Quan,Wang, KeWei,Wei, Ningning,Yin, Zhengji,Zhang, Yanru,Zhou, Qiqi,Zhu, Wei
supporting information, p. 16282 - 16292 (2021/11/12)
Transient receptor potential ankyrin 1 (TRPA1) channel, as a nonselective ligand-gated cation channel robustly in dorsal root ganglion sensory neurons, is implicated in sensing noxious stimuli and nociceptive signaling. However, small-molecule tools targeting TRPA1 lack temporal and spatial resolution, limiting their use for validation of TRPA1 as a therapeutic target for pain. In our previous work, we found that 4,4′-(diazene-1,2-diyl)dianiline (AB1) is a photoswitchable TRPA1 agonist, but the poor water solubility and activity hinder its further development. Here, we report a series of specific and potent azobenzene-derived photoswitchable TRPA1 agonists (series 1 and 2) that enable optical control of the TRPA1 channel. Two representative compounds 1g and 2c can alleviate capsaicin-induced pain in the cheek model of mice through channel desensitization but not in TRPA1 knockout mice. Taken together, our findings demonstrate that photoswitchable TRPA1 agonists can be used as pharmacological tools for study of pain signaling.