23589-80-2Relevant 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.).
Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles
Strelnikova, Julia O.,Rostovskii, Nikolai V.,Starova, Galina L.,Khlebnikov, Alexander F.,Novikov, Mikhail S.
, p. 11232 - 11244 (2018/09/06)
An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.
Studies of the cyclocondensation of o-aminophenyl-substituted ketoximes and amidoximes with carbonyl compounds giving quinazoline derivatives
Lessel
, p. 397 - 402 (2007/10/02)
Heating of o-amino-substituted ketoximes and amidoximes 3 with aldehydes and ketones gives the heterocyclic amidine- or quinazoline-N-oxides 5, respectively, from anthranilic acid amidoxime (3c) and diethyl carbonate the oxadiazolone 12 is formed. Thermol
1,2,4-Oxadiazolonylacetyl penicillins
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, (2008/06/13)
1,2,4-Oxadiazolonylacetyl penicillins and cephalosporins of the general formula SPC1 Wherein A is either SPC2 R1 is hydrogen, lower alkyl or phenyl-lower alkyl; R2 is hydrogen, lower alkyl, phenyl, hydroxyphenyl, thienyl, furyl, or p
