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Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes

,  , 
Alexander Sergeyevich Kulikov 1
Alexander Sergeyevich Kulikov
, 
Vadim Vadimovich Kachala 1
Vadim Vadimovich Kachala
, 
Nina Nikolaevna Makhova 1
Nina Nikolaevna Makhova
10.1016/j.mencom.2015.07.007
Published 2015-07-08
Communication , Volume 25, Issue 4, 257-259
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Fershtat L. L. et al. Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 257-259.
GOST all authors (up to 50) Copy
Fershtat L. L., Ashirbaev S. S., Kulikov A. S., Kachala V. V., Makhova N. N. Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes // Mendeleev Communications. 2015. Vol. 25. No. 4. pp. 257-259.
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TY - JOUR
DO - 10.1016/j.mencom.2015.07.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.007
TI - Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes
T2 - Mendeleev Communications
AU - Fershtat, Leonid Leonidovich
AU - Ashirbaev, Salavat Sagitovich
AU - Kulikov, Alexander Sergeyevich
AU - Kachala, Vadim Vadimovich
AU - Makhova, Nina Nikolaevna
PY - 2015
DA - 2015/07/08
PB - Mendeleev Communications
SP - 257-259
IS - 4
VL - 25
ER -
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@article{2015_Fershtat,
author = {Leonid Leonidovich Fershtat and Salavat Sagitovich Ashirbaev and Alexander Sergeyevich Kulikov and Vadim Vadimovich Kachala and Nina Nikolaevna Makhova},
title = {Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.007},
number = {4},
pages = {257--259},
doi = {10.1016/j.mencom.2015.07.007}
}
MLA
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Fershtat, Leonid Leonidovich, et al. “Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes.” Mendeleev Communications, vol. 25, no. 4, Jul. 2015, pp. 257-259. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.07.007.

Abstract

The [3 + 2] cycloaddition of azidofuroxans to internal and terminal acetylenes was found to occur only in ionic liquids on heating and afford (1H-1,2,3-triazol-1-yl)furoxans in moderate to good yields. The reaction with terminal acetylenes proceeds with high regio- selectivity.

References

1.
Searching for new NO-donor aspirin-like molecules: Furoxanylacyl derivatives of salicylic acid and related furazans
Lazzarato L., Cena C., Rolando B., Marini E., Lolli M.L., Guglielmo S., Guaita E., Morini G., Coruzzi G., Fruttero R., Gasco A.
Bioorganic and Medicinal Chemistry, 2011
2.
Furoxans (1,2,5-Oxadiazole-N-Oxides) as Novel NO Mimetic Neuroprotective and Procognitive Agents
Schiefer I.T., VandeVrede L., Fa’ M., Arancio O., Thatcher G.R.
Journal of Medicinal Chemistry, 2012
3.
Design, Synthesis, and Pharmacological Evaluation of Novel Hybrid Compounds to Treat Sickle Cell Disease Symptoms. Part II: Furoxan Derivatives
Dos Santos J.L., Lanaro C., Chelucci R.C., Gambero S., Bosquesi P.L., Reis J.S., Lima L.M., Cerecetto H., González M., Costa F.F., Chung M.C.
Journal of Medicinal Chemistry, 2012
4.
Fershtat L.L., Epishina M.A., Kulikov A.S., Makhova N.N.
Mendeleev Communications, 2015
6.
Ananikov V.P., Khokhlova E.A., Egorov M.P., Sakharov A.M., Zlotin S.G., Kucherov A.V., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications, 2015
7.
Formal [3+3]-cycloaddition of 3-methyl-5,6-dihydro-4H-1,2-oxazine-N-oxides with cyclopropane dicarboxylates under hyperbaric conditions
Tabolin A.A., Novikov R.A., Khomutova Y.A., Zharov A.A., Stashina G.A., Nelyubina Y.V., Tomilov Y.V., Ioffe S.L.
Tetrahedron Letters, 2015
9.
L. V. Batog, L.S. Konstantinova, V. Yu. Rozhkov, Yu. A. Strelenko, O.V. Lebedev and L. I. Khmel’nitskii, Chem. Heterocycl. Compd. (Engl. Transl.), 2000, 36, 91.(Khim. Geterotsikl. Soedin., 2000, 100).
10.
Seregin I.V., Batog L.V., Makhova N.N.
Mendeleev Communications, 2002
11.
Synthesis of (1,2,3-triazol-1-yl)furazans. 2. Reaction of azidofurazans with morpholinonitroethene
Batog L.V., Rozhkov V.Y., Strelenko Y.A., Lebedev O.V., Khmel'nitskii L.I.
Chemistry of Heterocyclic Compounds, 2000
12.
Batog L.V., Rozhkov V.Y., Struchkova M.I.
Mendeleev Communications, 2002
13.
V. Yu. Rozhkov, L.V. Batog and M. I. Struchkova, Russ. Chem. Bull., Int. Ed., 2005, 54, 1923.(Izv. Akad. Nauk, Ser. Khim., 2005, 1866).
14.
L. V. Batog, V. Yu. Rozhkov, M.I. Struchkova, A.S. Kulikov, N.N. Makhova, Russ. Chem. Bull., Int. Ed., 2013, 62, 1391.(Izv. Akad. Nauk, Ser. Khim., 2013, 1391).
15.
Rozhkov V.Y., Batog L.V., Shevtsova E.K., Struchkova M.I.
Mendeleev Communications, 2004
16.
L. V. Batog, V. Yu. Rozhkov, Yu. V. Khropov, N.V. Pyatakova, O.G. Busigina, I.S. Severina and N. N. Makhova, RF Patent 2158265, 2000.
17.
I. S. Severina, N.V. Pyatakova, A. Yu. Shchegolev, V. Yu. Rozhkov, L.V. Batog and N. N. Makhova, Biochem. (Moscow) Suppl. B: Biomed. Chem., 2014, 8, 27.
18.
Synthesis and in Vitro Characterization of 1-(4-Aminofurazan-3-yl)-5-dialkylaminomethyl-1H-[1,2,3]triazole-4-carboxylic Acid Derivatives. A New Class of Selective GSK-3 Inhibitors
Olesen P.H., Sørensen A.R., Ursø B., Kurtzhals P., Bowler A.N., Ehrbar U., Hansen B.F.
Journal of Medicinal Chemistry, 2003
19.
Synthesis and antineoplastic properties of (1H-1,2,3-triazol-1-yl)furazans
Kulikov A.S., Epishina M.A., Batog L.V., Rozhkov V.Y., Makhova N.N., Konyushkin L.D., Semenova M.N., Semenov V.V.
Russian Chemical Bulletin, 2013
20.
No-Mimetic Furoxans: Arylsulphonylfuroxans and Related Compounds
Ferioli R., Fazzini A., Folco G.C., Fruttero R., Calvino R., Gasco A., Bongrani S., Civelli M.
Pharmacological Research, 1993
21.
Role of guanylyl cyclase and cGMP-dependent protein kinase in long-term potentiation
Zhuo M., Hu Y., Schultz C., Kandel E.R., Hawkins R.D.
Nature, 1994
22.
A new class of furoxan derivatives as NO donors: mechanism of action and biological activity
Ferioli R., Folco G.C., Ferretti C., Gasco A.M., Medana C., Fruttero R., Civelli M., Gasco A.
British Journal of Pharmacology, 1995
23.
Vasorelaxant and antiplatelet activity of 4,7-dimethyl-1,2,5-oxadiazolo[3,4-d]pyridazine 1,5,6-trioxide: Role of soluble guanylate cyclase, nitric oxide and thiols
Kots A.Y., Grafov M.A., Khropov Y.V., Betin V.L., Belushkina N.N., Busygina O.G., Yazykova M.Y., Ovchinnikov I.V., Kulikov A.S., Makhova N.N., Medvedeva N.A., Bulargina T.V., Severina I.S.
British Journal of Pharmacology, 2000
25.
G. R. J. Thatcher, A.C. Nicolescu, B.M. Bennett and Toader, Free Radical Biol. Med., 2004, 37, 1122.
26.
Stereoselective Synthesis of (E)-2-Hydroxyimino-2-phenylacetonitrile by Photolysis of 4-Azido-3-phenylfurazan 2-Oxide
Kunai A., Doi T., Nagaoka T., Yagi H., Sasaki K.
Bulletin of the Chemical Society of Japan, 1990
27.
Dinitrogen trioxide-mediated domino process for the regioselective construction of 4-nitrofuroxans from acrylic acids
Fershtat L.L., Struchkova M.I., Goloveshkin A.S., Bushmarinov I.S., Makhova N.N.
Heteroatom Chemistry, 2014
30.
Petukhova V.Y., Pleshchev M.I., Fershtat L.L., Kuznetsov V.V., Kachala V.V., Makhova N.N.
Mendeleev Communications, 2012
31.
Pleshchev M.I., Petukhova V.Y., Kuznetsov V.V., Khakimov D.V., Pivina T.S., Struchkova M.I., Nelyubina Y.V., Makhova N.N.
Mendeleev Communications, 2013
32.
Reaction of 1,2-dialkyldiaziridines and 1,2,3-trialkyldiaziridines with methyl propiolate in ionic liquids and in organic solvents
Petukhova V.Y., Fershtat L.L., Kachala V.V., Kuznetsov V.V., Khakimov D.V., Pivina T.S., Makhova N.N.
Journal of Heterocyclic Chemistry, 2013
33.
Pleshchev M.I., Epishina M.A., Kachala V.V., Kuznetsov V.V., Goloveshkin A.S., Bushmarinov I.S., Makhova N.N.
Mendeleev Communications, 2013