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1.
Marina Tarasenko Nikolay Duderin Tatyana Sharonova Sergey Baykov Anton Shetnev Alexey V. Smirnov 《Tetrahedron letters》2017,58(37):3672-3677
An efficient and mild one-pot protocol has been developed for the synthesis of 1,2,4-oxadiazoles via the reaction of amidoximes with dicarboxylic acid anhydrides in a NaOH/DMSO medium. The method allows the synthesis of diversely substituted carboxylic acids bearing the 1,2,4-oxadiazole motif, – a popular building block for pharmaceutical research, in moderate to excellent yields. The reaction scope includes aromatic and heteroaromatic amidoximes as well as five-, six- and seven-membered anhydrides. The advantages of this procedure are proven gram-scalability and the use of inexpensive starting materials, which from a process chemistry point of view are essential for future industrial applications. 相似文献
2.
Sofia I. Presnukhina Marina V. Tarasenko Kirill K. Geyl Svetlana O. Baykova Sergey V. Baykov Anton A. Shetnev Vadim P. Boyarskiy 《Molecules (Basel, Switzerland)》2022,27(21)
We have developed a simple and convenient method for the synthesis of 3-aryl- and 3-hetaryl-1,2,4-oxadiazin-5-ones bearing an easily functionalizable (methoxycarbonyl)methyl group at position 6 via the reaction of aryl or hetaryl amidoximes with maleates or fumarates. The conditions for this reaction were optimized. Different products can be synthesized selectively in good yields depending on the base used and the ratio of reactants: substituted (1,2,4-oxadiazin-6-yl)acetic acids, corresponding methyl esters, or hybrid 3-(aryl)-6-((3-(aryl)-1,2,4-oxadiazol-5-yl)methyl)-4H-1,2,4-oxadiazin-5(6H)-ones. The reaction is tolerant to substituents’ electronic and steric effects in amidoximes. As a result, a series of 2-(5-oxo-3-(p-tolyl)-5,6-dihydro-4H-1,2,4-oxadiazin-6-yl)acetic acids, their methyl esters, and 1,2,4-oxadiazoles based on them were prepared and characterized by HRMS, 1H, and 13C NMR spectroscopy. The structures of three of them were elucidated with X-ray diffraction. 相似文献
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Mikherdov A. S. Baikov S. V. Proskurina I. K. Shetnev A. A. Kotov A. D. 《Russian Journal of General Chemistry》2019,89(10):2062-2068
Russian Journal of General Chemistry - The reaction of bis(cyclohexylisocyanide) complex of Pd(II) with substituted benzo[d]thiazole-2-amines in the presence of triethanolamine as the base has lead... 相似文献
5.
Shetnev A. A. Vasilieva E. A. Proskurina I. K. Forostyanko A. S. Presnukhina S. I. Tarasenko M. V. Lebedev A. S. Ivanovskii S. A. Kotov A. D. 《Russian Journal of Organic Chemistry》2022,58(3):306-314
Russian Journal of Organic Chemistry - A preparative procedure has been developed for the synthesis of a series of new medicinally relevant 3-aryl-5-(aryloxymethyl)-1,2,4-oxadiazoles in... 相似文献
6.
Tarasenko M. V. Kotlyarova V. D. Baykov S. V. Shetnev A. A. 《Russian Journal of General Chemistry》2021,91(5):768-778
Russian Journal of General Chemistry - An efficient one-pot method was developed for the synthesis of 2-(1,2,4-oxadiazol-5-yl)anilines via the reaction of amidoximes with isatoic anhydrides in a... 相似文献
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Makarova E. S. Kabanova M. V. Filimonov S. I. Shetnev A. A. Suponitsky K. Yu. 《Russian Chemical Bulletin》2022,71(5):1034-1042
Russian Chemical Bulletin - We proposed an approach for the preparation of substituted hexahydro-2H-chromeno-[4,3-d]pyrimidine-2,5-diones and studied their selective acylation and alkylation at the... 相似文献
8.
Sergey V. Baykov Artem V. Semenov Eugene A. Katlenok Anton A. Shetnev Nadezhda A. Bokach 《Molecules (Basel, Switzerland)》2021,26(11)
Structures of three tetrahalophthalic anhydrides (TXPA: halogen = Cl (TCPA), Br (TBPA), I (TIPA)) were studied by X-ray diffraction, and several types of halogen bonds (HaB) and lone pair···π-hole (lp···πh) contacts were revealed in their structures. HaBs involving the central oxygen atom of anhydride group (further X···O(anhydride) were recognized in the structures of TCPA and TBPA. In contrast, for the O(anhydride) atom of TIPA, only interactions with the π system (π-hole) of the anhydride ring (further lp(O)···πh) were observed. Computational studies by a number of theoretical methods (molecular electrostatic potentials, the quantum theory of atoms in molecules, the independent gradient model, natural bond orbital analyses, the electron density difference, and symmetry-adapted perturbation theory) demonstrated that the X···O(anhydride) contacts in TCPA and TBPA and lp(O)···πh in TIPA are caused by the packing effect. The supramolecular architecture of isostructural TCPA and TBPA was mainly affected by X···O(acyl) and X···X HaBs, and, for TIPA, the main contribution provided I···I HaBs. 相似文献
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Shetnev A. A. Pankratieva V. E. Kunichkina A. S. Vlasov A. S. Proskurina I. K. Kotov A. D. Korsakov M. K. 《Russian Journal of Organic Chemistry》2020,56(7):1181-1186
Russian Journal of Organic Chemistry - A new procedure has been proposed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with aldehydes in the superbasic system... 相似文献
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