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Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones

Alexander Yuryevich Belyy 1
Alexander Yuryevich Belyy
, 
Alena D Sokolova 1
Alena D Sokolova
, 
Rinat Faritovich Salikov 1
Rinat Faritovich Salikov
, 
Veronika Vladimirovna Litvinenko 1
Veronika Vladimirovna Litvinenko
, 
Dmitry Nikolaevich Platonov 1
Dmitry Nikolaevich Platonov
, 
10.71267/mencom.7616
Published 2025-02-18
Communication , Volume 35, Issue 2, 162-164
2
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Belyy A. Y. et al. Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones // Mendeleev Communications. 2025. Vol. 35. No. 2. pp. 162-164.
GOST all authors (up to 50) Copy
Belyy A. Y., Sokolova A. D., Salikov R. F., Litvinenko V. V., Platonov D. N., Tomilov Y. V. Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones // Mendeleev Communications. 2025. Vol. 35. No. 2. pp. 162-164.
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TY - JOUR
DO - 10.71267/mencom.7616
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7616
TI - Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones
T2 - Mendeleev Communications
AU - Belyy, Alexander Yuryevich
AU - Sokolova, Alena D
AU - Salikov, Rinat Faritovich
AU - Litvinenko, Veronika Vladimirovna
AU - Platonov, Dmitry Nikolaevich
AU - Tomilov, Yury Vasil'evich
PY - 2025
DA - 2025/02/18
PB - Mendeleev Communications
SP - 162-164
IS - 2
VL - 35
ER -
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@article{2025_Belyy,
author = {Alexander Yuryevich Belyy and Alena D Sokolova and Rinat Faritovich Salikov and Veronika Vladimirovna Litvinenko and Dmitry Nikolaevich Platonov and Yury Vasil'evich Tomilov},
title = {Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7616},
number = {2},
pages = {162--164},
doi = {10.71267/mencom.7616}
}
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Cite this
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Belyy, Alexander Yuryevich, et al. “Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones.” Mendeleev Communications, vol. 35, no. 2, Feb. 2025, pp. 162-164. https://mendcomm.colab.ws/publications/10.71267/mencom.7616.

Keywords

5-hydroxyisoquinolones
8π-electrocyclic ring-opening
cycloheptatriene
cycloheptatrienyl anion
dritterion
fluorescent dyes
large Stokes-shift

Abstract

The reaction of hexa(methoxycarbonyl)cycloheptatrienyl anion with amines affords 5-hydroxyisoquinolones bearing four 4,6,7,8-positioned methoxycarbonyl groups and having unsubstituted C3H unit. The reaction is selective due to better steric availability and both charge and orbital distribution within the seven-membered ring and may proceed through a nucleophilic attack on the allyl-anionic moiety.

Funders

Russian Science Foundation
23-23-00624

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