89804-66-0Relevant academic research and scientific papers
Electrochemical synthesis of 1,2,4-oxadiazoles from amidoximes through dehydrogenative cyclization
Hu, Aixi,Jiang, chan,Li, mingfang,Xu, Leitao,Ye, Jiao,Yi, Yangjie
, p. 10611 - 10616 (2021/12/27)
A convenient and efficient method for the generation of the iminoxy radical through anodic oxidation was developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles fromN-benzyl amidoximes. The transformation proceeds through 1.5-Hydrogen Atom Transfer (1,5-HAT) and intramolecular cyclization. The process features simple operation, mild conditions, broad substrate scope and high functional group compatibility, and provides a facile and practical way for the preparation of 1,2,4-oxadiazoles.
One-pot synthesis of 3,5-diaryl substituted-1,2,4-oxadiazoles using gem -dibromomethylarenes
Vinaya, Kambappa,Chandrashekara, Ganganahalli K.,Shivaramu, Prasanna D.
, p. 690 - 696 (2019/09/06)
1,2,4-Oxadiazole is one of the most promising heterocyclic ring systems in medicinal chemistry. In the present paper, we report the method for an efficient one-pot synthesis of 3,5-diaryl substituted 1,2,4-oxadiazoles using a two-component reaction of gem-dibromomethylarenes with amidoximes in good yields. In this method, gem-dibromomethylarenes are used as benzoic acid equivalents for the efficient synthesis of aryl-substituted 1,2,4-oxadiazoles. It is anticipated that this methodology will have versatile applications in the practical syntheses of various molecules of both medicinal and material chemistry importance.
Facile room-temperature assembly of the 1,2,4-oxadiazole core from readily available amidoximes and carboxylic acids
Sharonova, Tatyana,Pankrat'eva, Vitalina,Savko, Polyna,Baykov, Sergey,Shetnev, Anton
supporting information, p. 2824 - 2827 (2018/06/13)
A one-pot ambient-temperature procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from amidoximes and carboxylic acids under superbase-promoted conditions is reported.
The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters
Baykov, Sergey,Sharonova, Tatyana,Shetnev, Anton,Rozhkov, Sergey,Kalinin, Stanislav,Smirnov, Alexey V.
, p. 945 - 951 (2017/01/25)
The first one-pot room-temperature protocol for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via the condensation between amidoximes and carboxylic acid esters in superbase medium MOH/DMSO is reported. A broad spectrum of alkyl, aryl and hetaryl amidoximes and esters was examined. This reaction route provides convenient access to 1,2,4-oxadiazoles, which is highly desirable because in the light of this privileged scaffold is recognized as an important core in the design of novel therapeutic agents and high-tech materials.
Synthesis of 1,2,4-Oxadiazoles via DDQ-Mediated Oxidative Cyclization of Amidoximes
Parker, Patrick D.,Pierce, Joshua G.
, p. 1902 - 1909 (2016/06/15)
An oxidative cyclization of amidoximes to form 1,2,4-oxadiazoles, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), is described. A range of alkyl, aryl, and heteroaryl substrates are tolerated under these conditions. This reaction serves as an alternate approach for the synthesis of functionally diverse oxadiazoles via a rapid and straightforward synthetic procedure.
A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes
Guo, Wei,Huang, Kunbo,Ji, Fanghua,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 8857 - 8860 (2015/05/20)
Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with inexpensive copper catalysts and green oxidants. It has the advantages of atom- and step-economy, good functional group tolerance, as well as operational simplicity.
Synthesis of 1,2,4-Triazoles and 1,2,4-Oxadiazoles
Lin, Yang-i,Hlavka, Joseph J.,Bitha, Panayoto,Lang, S. A.
, p. 1693 - 1695 (2007/10/02)
Monothiodiacylamines reacted regiospecifically with hydrazines and hydroxylamine to give substituted 1,2,4-triazoles and 1,2,4-oxadiazoles in excellent yields.
