41125-75-1Relevant academic research and scientific papers
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.).
5-Phenyl-1,3,4-oxadiazol-2(3 H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit
Mahy, William,Willis, Nicky J.,Zhao, Yuguang,Woodward, Hannah L.,Svensson, Fredrik,Sipthorp, James,Vecchia, Luca,Ruza, Reinis R.,Hillier, James,Kj?r, Svend,Frew, Sarah,Monaghan, Amy,Bictash, Magda,Salinas, Patricia C.,Whiting, Paul,Vincent, Jean-Paul,Jones, E. Yvonne,Fish, Paul V.
, p. 12942 - 12956 (2020/11/13)
Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-Triazole 7 as an attractive starting point for a structure-based drug design hit-To-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with drug-like chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.
Synthesizing method for medical intermediate oxazolone compound
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Paragraph 0037; 0038; 0039; 0040; 0041, (2016/10/10)
The invention relates to a synthesizing method for a compound shown in a formula (III). The method comprises the steps that in organic solvent, a compound shown in a formula (I) reacts with formaldehyde shown in a formula (II) on the condition that a catalyst, an oxidizing agent, a nitrogen source compound and an activating agent exist, aftertreatment is performed after reacting is finished, and then the compound shown in the formula (III) is obtained, wherein R is selected from H or C1-C6 alkyl or C1-C6 alkoxy or halogen. According to the method, through comprehensive selection and cooperation of the catalyst, the oxidizing agent, the nitrogen source compound, the activating agent and the solvent, the target product can be obtained at a high yield, and the good application prospect and industrialized production potential are achieved in the field of medical intermediate synthesizing.
Palladium-catalyzed oxidative O-H/N-H carbonylation of hydrazides: Access to substituted 1,3,4-oxadiazole-2(3 H)-ones
Ji, Fanghua,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
, p. 5713 - 5718 (2015/06/16)
A novel palladium-catalyzed oxidative annulation reaction for the C-O, C-N bond formations is developed. The intramolecular cyclocarbonylation provides an efficient and direct approach for the construction of valuable 1,3,4-oxadiazole-2(3H)-ones and their
Synthesis of 5-substituted-3H-[1,3,4]-oxadiazol-2-one derivatives: A carbon dioxide route (CDR)
Brahmayya,Dai, Shenghong A.,Suen
, p. 65351 - 65357 (2015/08/18)
A carbon dioxide route (CDR) for making biologically important 5-substituted-3H-[1,3,4]-oxadiazol-2-ones (SHOs) has been accomplished through synthesis and cyclization of a variety of hydrazides as the key intermediates. All of these hydrazides were prepared readily in 89-97% yields by reacting acid chlorides with a hydrazine monohydrate in the initial step. Then, SHOs were obtained in high yields from hydrazides by reacting them with carbon dioxide under basic conditions. More notable than the high yields, is that the present CDR process for the first time has succeeded in providing a straightforward cyclization reaction leading to SHO formation with simple reagents in ethanol solution.
Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl- methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition
Debnath, Kamalesh,Pathak, Sudipta,Pramanik, Animesh
, p. 896 - 899 (2013/02/25)
The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N′-(chloro-aryl- methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity.
Room-temperature copper-catalyzed oxidation of electron-deficient arenes and heteroarenes using air
Liu, Qiang,Wu, Pan,Yang, Yuhong,Zeng, Ziqi,Liu, Jie,Yi, Hong,Lei, Aiwen
, p. 4666 - 4670 (2012/06/30)
No pressure: The oxidation of aromatic C-H bonds at room temperature was realized through a copper-catalyzed "oxygenase-type" oxidation of arenes and heteroarenes in the presence of air (see scheme). The reaction involves an oxygen-atom transfer from O2 in the air onto the substrates. Copyright
Propylene oxide assisted one-pot, tandem synthesis of substituted-1,3,4- oxadiazole-2(3H)-ones in water
Yan, Xu,Zhou, Shuo,Wang, Yuanqiang,Ge, Zemei,Cheng, Tieming,Li, Runtao
, p. 7978 - 7983 (2012/09/21)
It has been developed for the synthesis of substituted-1,3,4-oxadiazole- 2(3H)-one derivatives via a novel one-pot, tandem procedure assisted by propylene oxide. The 5-substitued-1,3,4-oxadiazole-2(3H)-ones and 3,5-disubstitued-1,3,4-oxadiazole-2(3H)-ones were, respectively, obtained from three-component reaction of acylhydrazines, carbon disulfide, and propylene oxide, and four-component reaction of acylhydarazines, carbon disulfide, propylene oxide, and organic halides. The reactions were carried out using water as solvent in the presence of potassium phosphate to afford the expected products in good to excellent yields.
Efficient phosphonium-mediated synthesis of 2-amino-1,3,4-oxadiazoles
Levins, Christopher G.,Wan, Zhao-Kui
supporting information; experimental part, p. 1755 - 1758 (2009/04/12)
We present an efficient, room temperature procedure for the preparation of 2-amino-1,3,4-oxadiazoles. Oxadiazol-2-ones can be activated for SnAr substitution using phosphonium reagents (e.g., BOP). This approach provides convenient access to N,
