54122-73-5Relevant academic research and scientific papers
2-Amino-substituted oxadiazole derivatives and pharmaceutical composition comprising the same
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Paragraph 0074; 0076; 0083; 0084, (2016/11/21)
The present invention provides: a novel 2-amino-substituted oxadiazole derivative represented by Chemical Formula 1 and having an excellent Wnt gene expression controlling activity; a pharmaceutically allowable salt of the same; a method for producing the
Regioselective synthesis of 2-amino-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives via reagent-based cyclization of thiosemicarbazide intermediate
Yang, Seung-Ju,Lee, Seok-Hyeong,Kwak, Hyun-Jung,Gong, Young-Dae
, p. 438 - 444 (2013/04/10)
A regioselective, reagent-based method for the cyclization reaction of 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole core skeletons is described. The thiosemicarbazide intermediate 3 was reacted with EDC·HCl in DMSO or p-TsCl, triethylamine in N-
Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles
Piatnitski Chekler, Eugene L.,Elokdah, Hassan M.,Butera, John
supporting information; scheme or table, p. 6709 - 6711 (2009/04/07)
A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R1 and R2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented.
15N NMR study of substituted 2-(phenylamino)-5-phenyl-1,3,4- oxadiazoles
Gierczyk, Blazej,Nowak-Wydra, Barbara,Grajewski, Jakub,Zalas, Maciej
, p. 123 - 127 (2007/10/03)
Substituted 2-(phenylamino)-5-phenyl-1,3,4-oxadiazoles were studied by 15N NMR spectroscopy. All signals were assigned on the basis of HMQC and HMBC experiments. Chemical shifts values were correlated with empirical Hammett parameters as well a
Fragmentation and skeletal rearrangements of 2-arylylamino-5-aryl-1,3,4- oxadiazoles and their noncovalent complexes with cobalt cation and cyclodextrin studied by mass spectrometry
Franski, Rafal,Gierczyk, Blazej,Schroeder, Grzegorz
, p. 312 - 322 (2007/10/03)
Mass spectrometric fragmentation pathways of title compounds were studied by electron ionization (EI) and electrospray ionization (ESI) as methods of ion generation. To explain the observed complex skeletal rearrangements, tandem mass spectrometry, accurate mass measurement and isotope labeling (compounds containing one 13C atom in oxadiazole ring) were used. Loss of CO, N2 and H atoms under EI conditions led to the formation of 9,10-dihydroacridine-type ions, loss of NH3 under ESI conditions yielded the 4-phenylphthalazinone-type ions and the loss of HNCO under ESI conditions produced N-arylamino-benzonitrilium ions; however, this process can be affected by the electron-donor/electron-withdrawing properties of groups substituted at the phenyl rings. The ESI was used to study the complexes of the compounds with cobalt as well as with cyclodextrin. It was found that the compounds studied tend to form inclusion complexes with cyclodextrin of stoichiometry 1:1 and complexes of different stoichiometries with cobalt, although those of stoichiometry 6:1 and 4:1 are favored and the attachment of counter ion may stabilize the complexes 3:1 and 2:1. Copyright
A SYNTHESIS OF 1,3,4-OXADIAZOLES VIA THE AZA-WITTIG REACTION OF N-ACYLAMINO IMINOTRIPHENYLPHOSPHORANES
Froeyen, Paul
, p. 11 - 15 (2007/10/02)
The aza-Wittig reaction of N-acylamino iminotriphenylphosphoranes with carbon disulfide, isocyanates and isothiocyanates, lead to the very reactive heterocumulenic systems (5) and (2) which undergo spontaneous cyclization to 5-substituted 2-mercapto-1,3,4-oxadiazoles (6) and 2-amino-1,3,4-oxadiazoles (3), respectively.
