Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 23, Pages 15466-15475Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02243
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Funding
- Russian Foundation for Basic Research [19-03-00069]
- Russian Science Foundation [19-13-00238]
- Ministry of Science and Higher Education of the Russian Federation
- Russian Science Foundation [19-13-00238] Funding Source: Russian Science Foundation
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A straightforward synthesis of a series of previously unknown N-(1,2,5-oxadiazolyl)hydrazones through the diazotization/reduction/condensation cascade of amino-1,2,5-oxadiazoles was accomplished. The described protocol was suitable for a wide array of target hydrazones, which were prepared in good to high yields under smooth reaction conditions with very good functional group tolerance. Importantly, the presented approach unveils a direct route to in situ generation of previously inaccessible (1,2,5-oxadiazolyl)hydrazines. In addition, a first example of the ionic structure incorporating a protonated hydrazone motif linked to the 1,2,5-oxadiazole 2-oxide subunit was synthesized, indicating the stability of prepared compounds toward acid-promoted hydrolysis. Overall, this method provides a direct access to the isosteric analogues of drug candidates for treatment of various neglected diseases, thus enabling their potential application in medicinal chemistry and drug design.
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