Tetrahedron Letters, volume 57, issue 50, pages 5685-5689
Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions
Ovchinnikov I.V.
1
,
Struchkova Marina I.
1
,
Romanova Anna A
2, 3
,
Ananyev Ivan V
2, 3
,
Makhova Nina N.
1
3
Higher Chemical College, Russian Academy of Sciences, 125047 Moscow, Russian Federation
|
Publication type: Journal Article
Publication date: 2016-12-01
Journal:
Tetrahedron Letters
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.8
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A general and simple method for the preparation of under explored 3-aryl-4-hydroxyfuroxans by nucleophilic substitution of the nitro group in 3-aryl-4-nitrofuroxans using NaOH in H2O-THF has been developed. The methylation of 3-aryl-4-hydroxyfuroxans was studied with various methylating reagents (CH2N2, MeI, (MeO)2SO2) which showed for the first time that 3-aryl-4-hydroxyfuroxans are prone to side-chain prototropic tautomerism. Furoxan derivatives of a novel type, N(5)-alkylation products (3-aryl-5-methyl-1,2,5-oxadiazol-4(2H)-one 2-oxides), were synthesized under mild conditions, along with regioselective formation of the O-alkylation products (3-aryl-4-methoxyfuroxans).
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2
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12
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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. Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions // Tetrahedron Letters. 2016. Vol. 57. No. 50. pp. 5685-5689.
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Fershtat L. L., Epishina M. A., Ovchinnikov I., Struchkova M. I., Romanova A. A., Ananyev I. V., Makhova N. N. Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions // Tetrahedron Letters. 2016. Vol. 57. No. 50. pp. 5685-5689.
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TY - JOUR
DO - 10.1016/j.tetlet.2016.11.023
UR - https://doi.org/10.1016%2Fj.tetlet.2016.11.023
TI - Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions
T2 - Tetrahedron Letters
AU - Epishina, Margarita A.
AU - Struchkova, Marina I.
AU - Romanova, Anna A
AU - Fershtat, Leonid L.
AU - Ovchinnikov, I.V.
AU - Ananyev, Ivan V
AU - Makhova, Nina N.
PY - 2016
DA - 2016/12/01 00:00:00
PB - Elsevier
SP - 5685-5689
IS - 50
VL - 57
SN - 0040-4039
SN - 1873-3581
ER -
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@article{2016_Fershtat,
author = {Margarita A. Epishina and Marina I. Struchkova and Anna A Romanova and Leonid L. Fershtat and I.V. Ovchinnikov and Ivan V Ananyev and Nina N. Makhova},
title = {Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions},
journal = {Tetrahedron Letters},
year = {2016},
volume = {57},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016%2Fj.tetlet.2016.11.023},
number = {50},
pages = {5685--5689},
doi = {10.1016/j.tetlet.2016.11.023}
}
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Fershtat, Leonid L., et al. “Side-chain prototropic tautomerism of 4-hydroxyfuroxans in methylation reactions.” Tetrahedron Letters, vol. 57, no. 50, Dec. 2016, pp. 5685-5689. https://doi.org/10.1016%2Fj.tetlet.2016.11.023.