Route to 1,2,4- and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol

[Display omitted] •A new method for the synthesis of (1,2,4-oxadiazolyl)-1,2,5-oxadiazoles was developed.•The process involves a one-pot condensation/oxidation sequence.•Previously unknown rearrangement in a furoxan series was found. A novel one-pot approach for the synthesis of 1,2,4- and 1,2,5-oxa...

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Bibliographic Details
Published in:Tetrahedron letters 2020-03, Vol.61 (13), p.151678, Article 151678
Main Authors: Teslenko, Fedor E., Churakov, Artem I., Larin, Alexander A., Ananyev, Ivan V., Fershtat, Leonid L., Makhova, Nina N.
Format: Article
Language:English
Subjects:
Condensation
Methods
Nitrogen heterocycles
Oxadiazoles
Synthetic
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Summary:[Display omitted] •A new method for the synthesis of (1,2,4-oxadiazolyl)-1,2,5-oxadiazoles was developed.•The process involves a one-pot condensation/oxidation sequence.•Previously unknown rearrangement in a furoxan series was found. A novel one-pot approach for the synthesis of 1,2,4- and 1,2,5-oxadiazole ring assemblies has been developed. The synthetic strategy involves the condensation of furoxanyl amidoximes with aldehydes and subsequent iodine-mediated oxidation of the intermediate 1,2,4-oxadiazolines. The analogous reaction of 4-aminofuroxanyl-3-carboxamidoxime results not only in formation of the 1,2,4-oxadiazole subunit, but also rearrangement of the furoxan ring to the furazan one, which is the first example of a Lewis acid-promoted rearrangement in a furoxan series.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151678