Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety
Vladislava V Matveevskaya
1
,
Nikolay Duderin
2
,
Tatyana Sharonova
2
,
Sergey V Baykov
2
,
Anton A Shetnev
3
,
ALEXEY V. SMIRNOV
2
Publication type: Journal Article
Publication date: 2017-09-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
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.
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35
Total citations:
35
Citations from 2024:
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(11%)
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GOST
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Matveevskaya V. V. et al. Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety // Tetrahedron Letters. 2017. Vol. 58. No. 37. pp. 3672-3677.
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Matveevskaya V. V., Duderin N., Sharonova T., Baykov S. V., Shetnev A. A., SMIRNOV A. V. Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety // Tetrahedron Letters. 2017. Vol. 58. No. 37. pp. 3672-3677.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/j.tetlet.2017.08.020
UR - https://doi.org/10.1016/j.tetlet.2017.08.020
TI - Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety
T2 - Tetrahedron Letters
AU - Matveevskaya, Vladislava V
AU - Duderin, Nikolay
AU - Sharonova, Tatyana
AU - Baykov, Sergey V
AU - Shetnev, Anton A
AU - SMIRNOV, ALEXEY V.
PY - 2017
DA - 2017/09/01
PB - Elsevier
SP - 3672-3677
IS - 37
VL - 58
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2017_Matveevskaya,
author = {Vladislava V Matveevskaya and Nikolay Duderin and Tatyana Sharonova and Sergey V Baykov and Anton A Shetnev and ALEXEY V. SMIRNOV},
title = {Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety},
journal = {Tetrahedron Letters},
year = {2017},
volume = {58},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.tetlet.2017.08.020},
number = {37},
pages = {3672--3677},
doi = {10.1016/j.tetlet.2017.08.020}
}
Cite this
MLA
Copy
Matveevskaya, Vladislava V., et al. “Room-temperature synthesis of pharmaceutically important carboxylic acids bearing the 1,2,4-oxadiazole moiety.” Tetrahedron Letters, vol. 58, no. 37, Sep. 2017, pp. 3672-3677. https://doi.org/10.1016/j.tetlet.2017.08.020.
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