185557-63-5Relevant articles and documents
Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts
Soldatova, Natalia S.,Semenov, Artem V.,Geyl, Kirill K.,Baykov, Sergey V.,Shetnev, Anton A.,Konstantinova, Anna S.,Korsakov, Mikhail M.,Yusubov, Mekhman S.,Postnikov, Pavel S.
supporting information, p. 3566 - 3576 (2021/06/16)
Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).
SUBSTITUENT-INCLUDING UREA COMPOUND
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Paragraph 0561; 0571-0573, (2021/12/03)
An object of the present invention is to provide a compound that has a specific chemical structure having an activation effect on SIRT6 and is useful as an active component for preventing and treating inflammatory diseases. The present invention relates to a compound represented by Formula (1) or a pharmaceutically acceptable salt thereof. (Each symbol in Formula (1) has the same definition as that described in the specification.)
Green synthesis method of oxadiazole derivatives
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Paragraph 0018-0019; 0035-0038, (2019/01/08)
The invention relates to the field of organic chemistry, overcomes disadvantages in the synthesis of oxadiazole derivatives in the prior art, and provides a green synthesis method of the oxadiazole derivatives. The method comprises the following specific steps: (1) adding a basic reagent, dropwise adding a carbonylation reagent, stirring evenly, and back-flowing at 100 DEG C, wherein water is usedas a solvent, N-hydroxybenzamidine or substituted N-hydroxybenzamidine is used as a raw material, the reaction time is 1-5 hours; and (2) after the reaction is finished, cooling, standing, adjustingpH to 3-4 with 1 mol/L diluted HCl acidification reaction solution, performing suction filtration, collecting filter cakes, washing the filter cakes with water, and performing vacuum drying to finallyobtain the oxadiazole derivative. N-hydroxybenzamidine or substituted N-hydroxybenzamidine and a carbonylation reagent are used as the raw materials, under the action of the basic reagent, the oxadiazole derivatives can be synthesized in one step in water, and the two steps of esterification and cyclization are simplified to one step, thus greatly shortening the reaction time and increasing the reaction yield. The method has the advantages of being mild in reaction conditions, convenient to separate and purify, green and environmentally friendly.