Chemistry of Heterocyclic Compounds, volume 51, issue 2, pages 176-186
Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives
Publication type: Journal Article
Publication date: 2015-02-01
Journal:
Chemistry of Heterocyclic Compounds
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.5
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
We report a general method for the synthesis of previously unknown heterocyclic systems containing furoxan and heterocyclic fragments linked by S- and О-bridges, based on nucleophilic substitution of nitro group in 4-nitrofuroxans with HetS and HetO groups introduced by reactions with hetarylthiols and hydroxy heterocycles in 1,8-diazabicyclo[5.4.0]undec-7-ene/МеCN system at room temperature. We showed that hetarylthiols reacted with 4-nitrofuroxans containing aliphatic, benzyl, and aromatic substituents at the ring С-3 atom, allowing to obtain a library of previously unknown hetarylsulfanylfuroxans, while the reaction with hydroxy heterocycles was successful only in the case of 4-nitro-3-phenylfuroxan, the rest of the nitrofuroxans showing low reactivity, and substitution products could be obtained only in certain cases. 4-Nitrofuroxans with electron-withdrawing substituents (NO2, CONH2) acted as oxidants, forming 1,2-di(hetaryl)disulfides.
Citations by journals
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8
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Mendeleev Communications
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Mendeleev Communications
8 publications, 26.67%
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7 publications, 23.33%
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Tetrahedron Letters
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RSC Advances
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3 publications, 10%
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2 publications, 6.67%
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Russian Chemical Reviews
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2 publications, 6.67%
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Tetrahedron
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1 publication, 3.33%
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ChemMedChem
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ChemMedChem
1 publication, 3.33%
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European Journal of Organic Chemistry
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European Journal of Organic Chemistry
1 publication, 3.33%
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ChemistrySelect
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ChemistrySelect
1 publication, 3.33%
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Comprehensive Heterocyclic Chemistry IV
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Comprehensive Heterocyclic Chemistry IV
1 publication, 3.33%
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Citations by publishers
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Elsevier
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Elsevier
13 publications, 43.33%
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Springer Nature
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Springer Nature
9 publications, 30%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
3 publications, 10%
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Wiley
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Wiley
3 publications, 10%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
2 publications, 6.67%
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4
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14
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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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Fershtat L. L. et al. Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives // Chemistry of Heterocyclic Compounds. 2015. Vol. 51. No. 2. pp. 176-186.
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Fershtat L. L., Epishina M. A., Kulikov A. S., Struchkova M. I., Makhova N. N. Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives // Chemistry of Heterocyclic Compounds. 2015. Vol. 51. No. 2. pp. 176-186.
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TY - JOUR
DO - 10.1007/s10593-015-1678-5
UR - https://doi.org/10.1007%2Fs10593-015-1678-5
TI - Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives
T2 - Chemistry of Heterocyclic Compounds
AU - Fershtat, Leonid L
AU - Epishina, Margarita A.
AU - Kulikov, Alexander S.
AU - Struchkova, Marina I.
AU - Makhova, Nina N
PY - 2015
DA - 2015/02/01 00:00:00
PB - Springer Nature
SP - 176-186
IS - 2
VL - 51
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2015_Fershtat,
author = {Leonid L Fershtat and Margarita A. Epishina and Alexander S. Kulikov and Marina I. Struchkova and Nina N Makhova},
title = {Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives},
journal = {Chemistry of Heterocyclic Compounds},
year = {2015},
volume = {51},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007%2Fs10593-015-1678-5},
number = {2},
pages = {176--186},
doi = {10.1007/s10593-015-1678-5}
}
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Fershtat, Leonid L., et al. “Synthesis of hetarylsulfanyl- and hetaryloxyfuroxans by nucleophilic substitution of nitro group in nitrofuroxans with heterocyclic thiol and hydroxy derivatives.” Chemistry of Heterocyclic Compounds, vol. 51, no. 2, Feb. 2015, pp. 176-186. https://doi.org/10.1007%2Fs10593-015-1678-5.