55151-97-8Relevant academic research and scientific papers
One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate
Amarasinghe, Kande K.D.,Maier, Matthew B.,Srivastava, Anil,Gray, Jeffrey L.
, p. 3629 - 3631 (2007/10/03)
A convenient one-pot synthesis of 1,2,4-oxadiazoles is described. The condensation of carboxylic acid esters and amidoximes in the presence of potassium carbonate was employed to synthesize a variety of mono-, bis- and tris-oxadiazoles in moderate to exce
Synthesis of 3,5-disubstituted-1,2,4-oxadiazoles using tetrabutylammonium fluoride as a mild and efficient catalyst
Gangloff, Anthony R.,Litvak, Joane,Shelton, Emma J.,Sperandio, David,Wang, Vivian R.,Rice, Kenneth D.
, p. 1441 - 1443 (2007/10/03)
Tetrabutylammonium fluoride (TBAF) was found to be a mild and efficient catalyst for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles. Using 0.1 - 1.0 equivalents of TBAF in THF for 1 - 24 h at room temperature, alkanoyl- and aroyloxyamidines were converted in high yield to the corresponding 3,5-disubstituted-1,2,4-oxadiazoles. A variety of R and R′ substituents were investigated.
THE PHOTOELIMINATION OF N-NITROSO-N-ACETYL-α-AMINO-ACIDS; A NEW SYNTHESIS OF 1,2,4-OXADIAZOLES
Chow, Yuan L.,Polo, Joel S.
, p. 727 - 734 (2007/10/02)
The excitation of N-nitroso-N-acetyl-α-aminoacids, nitrosopeptide model compounds, under neutral and weakly basic conditions, caused the homolysis of the N-N bond followed by decarboxylation to give hyponitrous acid (HNO) and N-acetylimines which were susceptible to nucleophilic addition.While weak bases caused the carboxylate group to assist intramolecular rearrangement to a small extent, they functioned primarily to provide nucleophilic NO-, which initiated nucleophilic attack leading to the C-nitroso derivatives.These C-nitroso derivatives spontaneously cyclized to 1,2,4-oxadiazoles much more rapidly than tautomerism to the corresponding oximes; the latter oximes failed to cyclize under the basic conditions.
