Russian Chemical Bulletin, volume 58, issue 2, pages 366-379
Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 • Et2 O
Publication type: Journal Article
Publication date: 2009-02-01
Journal:
Russian Chemical Bulletin
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.7
ISSN: 10665285, 15739171
General Chemistry
Abstract
The present study revealed two new reactions resulting in the diaziridine ring expansion, viz., the insertion of the CS2 molecule and the CN group of activated nitriles into the C—N bond of the diaziridine fragment of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes. These reactions can be performed only in ionic liquids in the presence of BF3 · Et2O as the catalyst. Based on these reactions, we developed simple one-pot methods for the synthesis of 3-aryldihydro-5 H-pyrazolo[1,2- c][1,3,4]thiadiazole-1-thiones and 1-aryl-6,7-dihydro-1 H,5H-pyrazolo-[1,2-a][1,2,4]triazoles in high yields. Dipolar intermediates of new reactions, which are direct precursors of the final products, were detected by NMR methods. One of the intermediates was isolated and characterized. The reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with benzoyl cyanide affords (2-benzoyrpyrazolidin-1-yl)(aryl)acetonitriles.
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Syroeshkina Yu. S. et al. Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 • Et2O // Russian Chemical Bulletin. 2009. Vol. 58. No. 2. pp. 366-379.
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Syroeshkina Yu. S., Kuznetsov V. V., Lyssenko K., Makhova N. N. Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 • Et2O // Russian Chemical Bulletin. 2009. Vol. 58. No. 2. pp. 366-379.
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TY - JOUR
DO - 10.1007/s11172-010-0018-2
UR - https://doi.org/10.1007%2Fs11172-010-0018-2
TI - Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 • Et2O
T2 - Russian Chemical Bulletin
AU - Syroeshkina, Yu S
AU - Kuznetsov, V. V.
AU - Lyssenko, K.A.
AU - Makhova, N N
PY - 2009
DA - 2009/02/01 00:00:00
PB - Springer Nature
SP - 366-379
IS - 2
VL - 58
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2009_Syroeshkina,
author = {Yu S Syroeshkina and V. V. Kuznetsov and K.A. Lyssenko and N N Makhova},
title = {Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 • Et2O},
journal = {Russian Chemical Bulletin},
year = {2009},
volume = {58},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007%2Fs11172-010-0018-2},
number = {2},
pages = {366--379},
doi = {10.1007/s11172-010-0018-2}
}
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Syroeshkina, Yu. S., et al. “Insertion of carbon disulfide and the nitrile group into the diaziridine ring of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids catalyzed by BF3 • Et2O.” Russian Chemical Bulletin, vol. 58, no. 2, Feb. 2009, pp. 366-379. https://doi.org/10.1007%2Fs11172-010-0018-2.
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