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Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process

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Tsyganov D. V. et al. Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 296-298.
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Tsyganov D. V., Samet A. V., Dorovatovskii P. V., Khrustalev V. N., Semenov V. V. Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 296-298.
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TY - JOUR
DO - 10.1016/j.mencom.2019.05.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.018
TI - Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process
T2 - Mendeleev Communications
AU - Tsyganov, Dmitry Vadimovich
AU - Samet, Alexander Viktorovich
AU - Dorovatovskii, Pavel Vladimirovich
AU - Khrustalev, Victor Nikolaevich
AU - Semenov, Victor Vladimirovich
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 296-298
IS - 3
VL - 29
ER -
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@article{2019_Tsyganov,
author = {Dmitry Vadimovich Tsyganov and Alexander Viktorovich Samet and Pavel Vladimirovich Dorovatovskii and Victor Nikolaevich Khrustalev and Victor Vladimirovich Semenov},
title = {Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.018},
number = {3},
pages = {296--298},
doi = {10.1016/j.mencom.2019.05.018}
}
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Tsyganov, Dmitry Vadimovich, et al. “Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process.” Mendeleev Communications, vol. 29, no. 3, Apr. 2019, pp. 296-298. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.018.

Abstract

Reaction of arylglyoxal oximes ArCOCH=NOH (Ar=4-MeOC6H4, Ph) with 5-arylfurazanopyrazines proceeds as vicarious nucleophilic substitution of hydrogen in pyrazine ring with the elimination of hyponitrous acid, affording 5-(aroylmethylidene)-6-aryl-4H-furazano[3,4-b]pyrazines. Structure of the product was confirmed by X-ray diffraction.

References

2.
Synthesis and SAR evaluation of oxadiazolopyrazines as selective Haemophilus influenzae antibacterial agents.
Beebe X., Nilius A.M., Merta P.J., Soni N.B., Bui M.H., Wagner R., Beutel B.A.
Bioorganic and Medicinal Chemistry Letters, 2003
3.
Structure-activity relationships of furazano[3,4-b]pyrazines as mitochondrial uncouplers.
Kenwood B.M., Calderone J.A., Taddeo E.P., Hoehn K.L., Santos W.L.
Bioorganic and Medicinal Chemistry Letters, 2015
4.
K. Lai, K.J. Wierenga, M. Tang, US Patent 8357701B2, 2013.
5.
H. Paulus, US Patent 7553832B2, 2009.
6.
D.E. Fisher, R. Haq, H.R.V. Widlund, US Patent 2014/0296223A1, 2014.
7.
The oxidation of 6‐ and 7‐aryl‐4(3h)‐pteridinones by immobilized arthrobacter M‐4 cells containing xanthine oxidase
8.
Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines
Coogan N.T., Chimes M.A., Raftery J., Mocilac P., Denecke M.A.
Journal of Organic Chemistry, 2015
10.
Scaling and assessment of data quality
Evans P.
Acta Crystallographica Section D Biological Crystallography, 2005
11.
iMOSFLM: a new graphical interface for diffraction-image processing withMOSFLM
Battye T.G., Kontogiannis L., Johnson O., Powell H.R., Leslie A.G.
Acta Crystallographica Section D Biological Crystallography, 2011
12.
Overview of theCCP4 suite and current developments
Winn M.D., Ballard C.C., Cowtan K.D., Dodson E.J., Emsley P., Evans P.R., Keegan R.M., Krissinel E.B., Leslie A.G., McCoy A., McNicholas S.J., Murshudov G.N., Pannu N.S., Potterton E.A., Powell H.R., et. al.
Acta Crystallographica Section D Biological Crystallography, 2011
13.
Crystal structure refinement withSHELXL
Sheldrick G.M.
Acta crystallographica. Section C, Structural chemistry, 2015
14.
Synthesis of furazano[3,4-b]pyrazine derivatives
Eremeev A.V., Andrianov V.G., Piskunova I.P.
Chemistry of Heterocyclic Compounds, 1978
15.
10.1016/j.mencom.2019.05.018_bib0055
1979
16.
α-Dicarbonylmonoxime als Nucleophile und Nachbargruppen / α-Dicarbonylmonoximes as Nucleophiles and Neighbour Groups
Möhrle H., Keller G.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999
17.
10.1016/j.mencom.2019.05.018_sbref0060b
Hahn
Pol. J. Chem., 1986
19.
Synthesis of novel functionally substituted pyridazines and oxazines
Hammouda M., Abou Zeid Z.M., Metwally M.A.
Chemistry of Heterocyclic Compounds, 2008
20.
Reactions of pyrazinium salts with phenols:from σH-adducts to SN Hproducts and transformations into benzo[b]furans
Verbitskiy E.V., Kvashnin Y.A., Slepukhin P.A., Kuchin A.V., Rusinov G.L., Chupakhin O.N., Charushina V.N.
Russian Chemical Bulletin, 2011
21.
9-Ethyl-3-{6-(het)aryl-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl}-9H-carbazoles: synthesis and study of sensitivity to nitroaromatic compounds
Verbitskiy E.V., Kvashnin Y.A., Baranova A.A., Yakovleva Y.A., Khokhlov K.О., Rusinov G.L., Charushin V.N.
Russian Chemical Bulletin, 2018
23.
Nucleophilic Substitution of Hydrogen in Heterocyclic Chemistry
Ma̧kosza M., Wojciechowski K.
Chemical Reviews, 2004
24.
10.1016/j.mencom.2019.05.018_sbref0070c
Terrier
Modern Nucleophilic Aromatic Substitution, 2013
26.
Direct arylalkenylation of furazano[3,4- b ]pyrazines via a new C–H functionalization protocol
Kazin N.A., Kvashnin Y.A., Irgashev R.A., Dehaen W., Rusinov G.L., Charushin V.N.
Tetrahedron Letters, 2015