Journal of Organic Chemistry, volume 85, issue 23, pages 15466-15475
Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade
Publication type: Journal Article
Publication date: 2020-11-13
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
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.
Citations by journals
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1
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Synthesis
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Synthesis
1 publication, 20%
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Russian Journal of Organic Chemistry
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Russian Journal of Organic Chemistry
1 publication, 20%
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MolBank
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MolBank
1 publication, 20%
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Progress in Heterocyclic Chemistry
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Progress in Heterocyclic Chemistry
1 publication, 20%
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Russian Journal of General Chemistry
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Russian Journal of General Chemistry
1 publication, 20%
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1
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Citations by publishers
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1
2
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Pleiades Publishing
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Pleiades Publishing
2 publications, 40%
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Thieme
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Thieme
1 publication, 20%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 20%
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Elsevier
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Elsevier
1 publication, 20%
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1
2
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Bystrov D. M. et al. Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade // Journal of Organic Chemistry. 2020. Vol. 85. No. 23. pp. 15466-15475.
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Bystrov D. M., Ananyev I. V., Fershtat L. L., Makhova N. N. Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade // Journal of Organic Chemistry. 2020. Vol. 85. No. 23. pp. 15466-15475.
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TY - JOUR
DO - 10.1021/acs.joc.0c02243
UR - https://doi.org/10.1021%2Facs.joc.0c02243
TI - Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade
T2 - Journal of Organic Chemistry
AU - Bystrov, Dmitry M.
AU - Ananyev, Ivan V
AU - Fershtat, Leonid L.
AU - Makhova, Nina N.
PY - 2020
DA - 2020/11/13 00:00:00
PB - American Chemical Society (ACS)
SP - 15466-15475
IS - 23
VL - 85
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2020_Bystrov,
author = {Dmitry M. Bystrov and Ivan V Ananyev and Leonid L. Fershtat and Nina N. Makhova},
title = {Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade},
journal = {Journal of Organic Chemistry},
year = {2020},
volume = {85},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021%2Facs.joc.0c02243},
number = {23},
pages = {15466--15475},
doi = {10.1021/acs.joc.0c02243}
}
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Bystrov, Dmitry M., et al. “Direct Synthesis of N-(1,2,5-Oxadiazolyl)hydrazones through a Diazotization/Reduction/Condensation Cascade.” Journal of Organic Chemistry, vol. 85, no. 23, Nov. 2020, pp. 15466-15475. https://doi.org/10.1021%2Facs.joc.0c02243.
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