Home / Publications / Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure

Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure

Alexandra Gennad'evna Kutasevich 1
Alexandra Gennad'evna Kutasevich
, 
Yana Sergeevna Novoselskaya 1
Yana Sergeevna Novoselskaya
, 
Elizaveta Aleksandrovna Kvyatkovskaya 1
Elizaveta Aleksandrovna Kvyatkovskaya
, 
Nikolay Aleksandrovich Nikolaev 2
Nikolay Aleksandrovich Nikolaev
,  , 
Fedor Ivanovich Zubkov 1
Fedor Ivanovich Zubkov
, 
Evgenia Valentinovna Nikitina 1
Evgenia Valentinovna Nikitina
2 Institute for High Pressure Physics, Russian Academy of Sciences, 108840 Troitsk, Moscow, Russian Federation
10.71267/mencom.7673
Published 2025-03-31
Communication , Volume 35, Issue 3, 252-254
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kutasevich A. G. et al. Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure // Mendeleev Communications. 2025. Vol. 35. No. 3. pp. 252-254.
GOST all authors (up to 50) Copy
Kutasevich A. G., Novoselskaya Y. S., Kvyatkovskaya E. A., Nikolaev N. A., Brazhkin V. V., Zubkov F. I., Nikitina E. V. Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure // Mendeleev Communications. 2025. Vol. 35. No. 3. pp. 252-254.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.71267/mencom.7673
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7673
TI - Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure
T2 - Mendeleev Communications
AU - Kutasevich, Alexandra Gennad'evna
AU - Novoselskaya, Yana Sergeevna
AU - Kvyatkovskaya, Elizaveta Aleksandrovna
AU - Nikolaev, Nikolay Aleksandrovich
AU - Brazhkin, Vadim Veniaminovich
AU - Zubkov, Fedor Ivanovich
AU - Nikitina, Evgenia Valentinovna
PY - 2025
DA - 2025/03/31
PB - Mendeleev Communications
SP - 252-254
IS - 3
VL - 35
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2025_Kutasevich,
author = {Alexandra Gennad'evna Kutasevich and Yana Sergeevna Novoselskaya and Elizaveta Aleksandrovna Kvyatkovskaya and Nikolay Aleksandrovich Nikolaev and Vadim Veniaminovich Brazhkin and Fedor Ivanovich Zubkov and Evgenia Valentinovna Nikitina},
title = {Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7673},
number = {3},
pages = {252--254},
doi = {10.71267/mencom.7673}
}
MLA
Cite this
MLA Copy
Kutasevich, Alexandra Gennad'evna, et al. “Tandem [4 + 2]/[4 + 2] cycloaddition of bis-furyl dienes with fumaric and maleic esters at ultra-high pressure.” Mendeleev Communications, vol. 35, no. 3, Mar. 2025, pp. 252-254. https://mendcomm.colab.ws/publications/10.71267/mencom.7673.

Keywords

1,4:5,8-diepoxynaphthalene
7-oxabicyclo[2.2.1]heptene
fumaric esters
furan
intramolecular Diels--Alder reaction
maleic esters
ultra-high pressure

Abstract

Employment of ultra-high pressures (15 kbar) at room temperature makes it possible to prepare 1,4:5,8-diepoxynaphthalenes annulated with other heterocycles from bisfurfuryl derivatives and fumaric/maleic esters. Such a reaction does not proceed under ordinary thermal conditions.

Funders

Russian Science Foundation
23--23-00577

References

1.
An IMDAF approach to annellated 1,4:5,8-diepoxynaphthalenes and their metathesis reaction leading to novel scaffolds displaying an antiproliferative activity toward cancer cells
Kvyatkovskaya E.A., Borisova K.K., Epifanova P.P., Senin A.A., Khrustalev V.N., Grigoriev M.S., Bunev A.S., Gasanov R.E., Polyanskii K.B., Zubkov F.I.
New Journal of Chemistry, 2021
2.
Synthetic applications of furan Diels-Alder chemistry
Oliver Kappe C., Shaun Murphree S., Padwa A.
Tetrahedron, 1997
5.
Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes.
Borisova K.K., Kvyatkovskaya E.A., Nikitina E.V., Aysin R.R., Novikov R.A., Zubkov F.I.
Journal of Organic Chemistry, 2018
6.
Diels-Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control.
Borisova K.K., Nikitina E.V., Novikov R.A., Khrustalev V.N., Dorovatovskii P.V., Zubavichus Y.V., Kuznetsov M.L., Zaytsev V.P., Varlamov A.V., Zubkov F.I.
Chemical Communications, 2018
10.
Domino Diels-Alder cycloadditions of arynes: new approach to elusive perylene derivatives.
Criado A., Peña D., Cobas A., Guitián E.
Chemistry - A European Journal, 2010
14.
Trends in the Diels–Alder reaction in polymer chemistry
Briou B., Améduri B., Boutevin B.
Chemical Society Reviews, 2021
18.
Stereoselective Tandem Cascade Furan Cycloadditions
Criado A., Vilas-Varela M., Cobas A., Pérez D., Peña D., Guitián E.
Journal of Organic Chemistry, 2013
20.
Constraining molecules at the closest approach: chemistry at high pressure
Schettino V., Bini R.
Chemical Society Reviews, 2007
21.
Hyperbaric reactions in organic synthesis. Progress from 2006 to 2021
Rulev A.Y., Zubkov F.I.
Organic and Biomolecular Chemistry, 2022
22.
Advances in Diels–Alder/aromatization of biomass furan derivatives towards renewable aromatic hydrocarbons
Li Z., Jiang Y., Li Y., Zhang H., Li H., Yang S.
Catalysis Science and Technology, 2022
23.
Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes
Kvyatkovskaya E.A., Epifanova P.P., Borisova K.K., Borovkova S.I., Grigoriev M.S., Zubkov F.I.
Chemistry of Heterocyclic Compounds, 2021
24.
The Diels–Alder reaction: A powerful tool for the design of drug delivery systems and biomaterials
Gregoritza M., Brandl F.P.
European Journal of Pharmaceutics and Biopharmaceutics, 2015
25.
N-(furfural) chitosan hydrogels based on Diels–Alder cycloadditions and application as microspheres for controlled drug release
Montiel-Herrera M., Gandini A., Goycoolea F.M., Jacobsen N.E., Lizardi-Mendoza J., Recillas-Mota M., Argüelles-Monal W.M.
Carbohydrate Polymers, 2015
27.
Potential use of the Diels-Alder reaction in biomedical and nanomedicine applications
Oluwasanmi A., Hoskins C.
International Journal of Pharmaceutics, 2021
28.
A new antitumour substance, 7-oxabicyclo (2.2.1)-5-heptene-2,3-dicarboxylic anhydride
Shimi I.R., Zaki Z., Shoukry S., Medhat A.M.
European Journal of Cancer and Clinical Oncology, 1982
29.
Crystal structure and Hirshfeld surface analysis of diethyl (3aS,3a1R,4S,5S,6R,6aS,7R,9aS)-3a1,5,6,6a-tetrahydro-1H,3H,4H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-4,5-dicarboxylate
Sadikhova N.D., Atioğlu Z., Guliyeva N.A., Podrezova A.G., Nikitina E.V., Akkurt M., Bhattarai A.
Acta Crystallographica Section E: Crystallographic Communications, 2024
30.
A Diels–Alder probe for discovery of natural products containing furan moieties
Eggly A.S., Otgontseren N., Roberts C.B., Alwali A.Y., Hennigan H.E., Parkinson E.I.
Beilstein Journal of Organic Chemistry, 2024