Home / Publications / Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans

Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans

Anatoly Nikolaevich Vereshchagin 1
Anatoly Nikolaevich Vereshchagin
Yuliya Evgenievna Ryzhkova 1
Yuliya Evgenievna Ryzhkova
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
Published 2021-04-28
CommunicationVolume 31, Issue 3, 347-349
4
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Elinson M. N. et al. Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 347-349.
GOST all authors (up to 50) Copy
Elinson M. N., Vereshchagin A. N., Ryzhkova Y. E., Egorov M. P. Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 347-349.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.04.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.021
TI - Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans
T2 - Mendeleev Communications
AU - Elinson, Michail Nikolaevich
AU - Vereshchagin, Anatoly Nikolaevich
AU - Ryzhkova, Yuliya Evgenievna
AU - Egorov, Mikhail Petrovich
PY - 2021
DA - 2021/04/28
PB - Mendeleev Communications
SP - 347-349
IS - 3
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Elinson,
author = {Michail Nikolaevich Elinson and Anatoly Nikolaevich Vereshchagin and Yuliya Evgenievna Ryzhkova and Mikhail Petrovich Egorov},
title = {Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.021},
number = {3},
pages = {347--349},
doi = {10.1016/j.mencom.2021.04.021}
}
MLA
Cite this
MLA Copy
Elinson, Michail Nikolaevich, et al. “Selective and efficient electrocatalytic way to spirobarbituric dihydrofurans.” Mendeleev Communications, vol. 31, no. 3, Apr. 2021, pp. 347-349. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.021.

Keywords

Cyclization
electrocatalysis
electrosynthesis
mediated electrolysis
spirobarbituric dihydrofurans

Abstract

Electrocatalytic cyclization of 6-hydroxy-5-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)(aryl)methyl]-1,3-dimethylpyrimidine-2,4-(1H,3H)-diones in alcohols in an undivided cell in the presence of sodium halides results in selective formation of substituted spirobarbituric dihydrofurans in 82–93% yields. Crystal structure of 3-(3-bromophenyl)-1′,3′,6,6-tetramethyl-3,5,6,7-tetrahydro-2′,4-dihydrospiro[benzofuran-2,5′-pyrimidine]-2′,4,4′,6′(1′H,3′H)-tetraone has been confirmed by X-ray diffraction data.

References

1.
10.1016/j.mencom.2021.04.021_sbref0005a
Organic Electrochemistry: Revised and Expanded, 2015
2.
Synthetic Organic Electrochemistry: Calling All Engineers
Yan M., Kawamata Y., Baran P.S.
Angewandte Chemie - International Edition, 2017
5.
Mediator oxidation systems in organic electrosynthesis
Ogibin Y.N., Elinson M.N., Nikishin G.I.
Russian Chemical Reviews, 2009
6.
10.1016/j.mencom.2021.04.021_sbref0020a
Arora
Int. J. Pharm. Sci. Res., 2012
7.
Estimation of biological affinity of nitrogen-containing conjugated heterocyclic pharmacophores
Kachaeva M.V., Obernikhina N.V., Veligina E.S., Zhuravlova M.Y., Prostota Y.O., Kachkovsky O.D., Brovarets V.S.
Chemistry of Heterocyclic Compounds, 2019
8.
The effect of the structure of derivatives of nitrogen-containing heterocycles on their anti-influenza activity
Gridina T.L., Fedchuk A.S., Basok S.S., Artemenko A.G., Ognichenko L.N., Shitikova L.I., Lutsyuk A.F., Gruzevskii A.A., Kuz’min V.E.
Chemistry of Heterocyclic Compounds, 2019
9.
Modern advances in heterocyclic chemistry in drug discovery
Taylor A.P., Robinson R.P., Fobian Y.M., Blakemore D.C., Jones L.H., Fadeyi O.
Organic and Biomolecular Chemistry, 2016
12.
5-Benzylbarbituric acid derivatives, potent and specific inhibitors of uridine phosphorylase.
Naguib F.N., Levesque D.L., Eng-Chi Wang, Panzica R.P., El Kouni M.H.
Biochemical Pharmacology, 1993
13.
Pyrimidine-2,4,6-Triones: A New Effective and Selective Class of Matrix Metalloproteinase Inhibitors
Grams F., Brandstetter H., DAlò S., Geppert D., Krell H., Leinert H., Livi V., Menta E., Oliva A., Zimmermann G.
Biological Chemistry, 2001
14.
Anti-Invasive, Antitumoral, and Antiangiogenic Efficacy of a Pyrimidine-2,4,6-trione Derivative, an Orally Active and Selective Matrix Metalloproteinases Inhibitor
Maquoi E., Sounni N.E., Devy L., Olivier F., Frankenne F., Krell H., Grams F., Foidart J., Noël A.
Clinical Cancer Research, 2004
15.
Pro- and antioxidant properties of uracil derivatives
Murinov Y.I., Grabovskii S.A., Kabal’nova N.N.
Russian Chemical Bulletin, 2019
17.
The use of spirocyclic scaffolds in drug discovery
Zheng Y., Tice C.M., Singh S.B.
Bioorganic and Medicinal Chemistry Letters, 2014
18.
Synthesis and pharmacological evaluation of spiro-analogues of 5-benzyl-5-ethyl barbituric acid.
King S.B., Stratford E.S., Craig C.R., Fifer E.K.
Pharmaceutical Research, 1995
20.
Proline Derived Spirobarbiturates as Highly Effective β-Turn Mimetics Incorporating Polar and Functionalizable Constraint Elements
Lomlim L., Einsiedel J., Heinemann F.W., Meyer K., Gmeiner P.
Journal of Organic Chemistry, 2008
22.
Structure-based design of potent and selective inhibitors of collagenase-3 (MMP-13)
Kim S., Pudzianowski A.T., Leavitt K.J., Barbosa J., McDonnell P.A., Metzler W.J., Rankin B.M., Liu R., Vaccaro W., Pitts W.
Bioorganic and Medicinal Chemistry Letters, 2005
23.
Latent inhibitors. Part 7. Inhibition of dihydro-orotate dehydrogenase by spirocyclopropanobarbiturates
Fraser W., Suckling C.J., Wood H.C.
Journal of the Chemical Society Perkin Transactions 1, 1990
24.
J. Duan, B. Jiang, L. Chen, Z. Lu, J. Barbosa and W. J. Pitts, US Patent 7294624 B2, 2007.
25.
Electrocatalytic stereoselective transformation of aldehydes and two molecules of pyrazolin-5-one into (R*,R*)-bis(spiro-2,4-dihydro-3H-pyrazol-3-one)cyclopropanes
26.
Electrochemical synthesis of cyclopropanes
Elinson M.N., Dorofeeva E.O., Vereshchagin A.N., Nikishin G.I.
Russian Chemical Reviews, 2015
29.
Elinson M.N., Feducovich S.K., Bushuev S.G., Zakharenkov A.A., Pashchenko D.V., Nikishin G.I.
Mendeleev Communications, 1998
30.
Elinson M.N., Vereshchagin A.N., Anisina Y.E., Leonova N.A., Egorov M.P.
Mendeleev Communications, 2020
31.
Vereshchagin A.N., Dorofeeva E.O., Elinson M.N., Korolev V.A., Egorov M.P.
Mendeleev Communications, 2019