One-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles containing an alkenyl moiety

Sidneva, Vera V.; Tarasenko, M. V.; Кофанов, Е. Р.

doi:10.1007/s10593-022-03096-5

Cited by 2 publications

(2 citation statements)

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“…Finally, a few reports indicated that DMSO can be replaced by DMF or DMA [ 125 , 126 , 127 , 128 ]. Straniero et al obtained two new 1,2,4-oxadiazole-based inhibitors of filamentous temperature-sensitive protein Z (FtsZ) for the treatment of drug-resistant bacterial infections ( Scheme 25 A) [ 125 ].…”

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

“…The resulting anthranilic diamides bearing the incorporated 1,2,4-oxadiazole moiety were obtained in moderate to good yields. Recently, Sidneva et al developed the one-pot protocol for the synthesis of 1,2,4-oxadiazole at room temperature via the reaction of cinnamic acids activated by ethyl chloroformate with amidoximes in the presence of KOH in dimethylacetamide (DMA) ( Scheme 25 C) [ 127 ]. In this case, yields of final heterocycles were comparable with previously reported data for reactions in DMSO.…”

Section: Base-induced Cyclodehydration Of O -Acyla...mentioning

confidence: 99%

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Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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1,2,4-Oxadiazole is an essential motif in drug discovery represented in many experimental, investigational, and marketed drugs. This review covers synthetic methods that allow the conversion of different types of organic compounds into 1,2,4-oxadiazole at ambient temperature and the practical application of the latter approaches for the preparation of pharmaceutically important molecules. The discussed methods are divided into three groups. The first combines two-stage protocols requiring the preliminary preparation of O-acylamidoximes followed by cyclization under the action of organic bases. The advantages of this route are its swiftness, high efficiency of the cyclization process, and uncomplicated work--up. However, it requires the preparation and isolation of O-acylamidoximes as a separate preliminary step. The second route is a one-pot synthesis of 1,2,4-oxadiazoles directly from amidoximes and various carboxyl derivatives or aldehydes in aprotic bipolar solvents (primarily DMSO) in the presence of inorganic bases. This recently proposed pathway proved to be highly efficient in the field of medicinal chemistry. The third group of methods consists of diverse oxidative cyclizations, and these reactions have found modest application in drug design thus far. It is noteworthy that the reviewed methods allow for obtaining 1,2,4-oxadiazoles with thermosensitive functions and expand the prospects of using the oxadiazole core as an amide- or ester-like linker in the design of bioactive compounds.

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