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

Teslenko F.E., Churakov A.I., Larin A.A., Ananyev I.V., Fershtat L.L., Makhova N.N.
Тип документаJournal Article
Дата публикации2020-03-26
Название журналаTetrahedron Letters
ИздательElsevier
КвартильQ2
ISSN00404039, 18733581
  • Organic Chemistry
  • Drug Discovery
  • Biochemistry
Краткое описание
Abstract 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.
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1. Teslenko F.E. и др. Route to 1,2,4- and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol // Tetrahedron Letters. 2020. Т. 61. № 13. С. 151678.
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TY - JOUR

DO - 10.1016/j.tetlet.2020.151678

UR - http://dx.doi.org/10.1016/j.tetlet.2020.151678

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

T2 - Tetrahedron Letters

AU - Teslenko, Fedor E.

AU - Churakov, Artem I.

AU - Larin, Alexander A.

AU - Ananyev, Ivan V.

AU - Fershtat, Leonid L.

AU - Makhova, Nina N.

PY - 2020

DA - 2020/03

PB - Elsevier BV

SP - 151678

IS - 13

VL - 61

SN - 0040-4039

ER -

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@article{2020,

doi = {10.1016/j.tetlet.2020.151678},

url = {https://doi.org/10.1016%2Fj.tetlet.2020.151678},

year = 2020,

month = {mar},

publisher = {Elsevier {BV}},

volume = {61},

number = {13},

pages = {151678},

author = {Fedor E. Teslenko and Artem I. Churakov and Alexander A. Larin and Ivan V. Ananyev and Leonid L. Fershtat and Nina N. Makhova},

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

}

MLA
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Teslenko, Fedor E. et al. “Route to 1,2,4- and 1,2,5-Oxadiazole Ring Assemblies via a One-Pot Condensation/oxidation Protocol.” Tetrahedron Letters 61.13 (2020): 151678. Crossref. Web.