Synthesis and cascade rearrangement of 3-arylazo-4-(3-ethoxycarbonylureido) furoxans
Publication type: Journal Article
Publication date: 2003-10-24
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Abstract3-Arylazo-4-(3-ethoxycarbonylureido)furoxans, which were synthesized by the reactions of 4-amino-3-arylazofuroxans with ethoxycarbonyl isocyanate, were subjected to cascade rearrangements under the action of potassium tert-butoxide in dimethylformamide or by heating in dimethyl sulfoxide to form 4-amino-2-aryl-5-nitro-2H-1,2,3-triazoles. X-ray diffraction study and quantum-chemical calculations (B3LYP/6-31G**) of one of ureidofuroxans demonstrated that the intramolecular contact between the carbonyl group and the nitrogen atom of furoxan corresponds to the charge transfer from the lone electron pair of the oxygen atom to the antibonding orbital of the N—O bond.
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Citations from 2024:
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Molotov S. I. et al. Synthesis and cascade rearrangement of 3-arylazo-4-(3-ethoxycarbonylureido) furoxans // Russian Chemical Bulletin. 2003. Vol. 52. No. 8. pp. 1829-1834.
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Molotov S. I., Kulikov A., Strelenko Y., Makhova N. N., Lyssenko K. Synthesis and cascade rearrangement of 3-arylazo-4-(3-ethoxycarbonylureido) furoxans // Russian Chemical Bulletin. 2003. Vol. 52. No. 8. pp. 1829-1834.
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TY - JOUR
DO - 10.1023/A:1026025225333
UR - https://doi.org/10.1023/A:1026025225333
TI - Synthesis and cascade rearrangement of 3-arylazo-4-(3-ethoxycarbonylureido) furoxans
T2 - Russian Chemical Bulletin
AU - Molotov, S I
AU - Kulikov, A.S
AU - Strelenko, Yu.A.
AU - Makhova, N N
AU - Lyssenko, K.A.
PY - 2003
DA - 2003/10/24
PB - Springer Nature
SP - 1829-1834
IS - 8
VL - 52
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2003_Molotov,
author = {S I Molotov and A.S Kulikov and Yu.A. Strelenko and N N Makhova and K.A. Lyssenko},
title = {Synthesis and cascade rearrangement of 3-arylazo-4-(3-ethoxycarbonylureido) furoxans},
journal = {Russian Chemical Bulletin},
year = {2003},
volume = {52},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1023/A:1026025225333},
number = {8},
pages = {1829--1834},
doi = {10.1023/A:1026025225333}
}
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MLA
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Molotov, S. I., et al. “Synthesis and cascade rearrangement of 3-arylazo-4-(3-ethoxycarbonylureido) furoxans.” Russian Chemical Bulletin, vol. 52, no. 8, Oct. 2003, pp. 1829-1834. https://doi.org/10.1023/A:1026025225333.