Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species
Тип публикации: Journal Article
Дата публикации: 2021-10-29
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SJR: 0.243
CiteScore: 2.7
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ISSN: 00093122, 15738353
Organic Chemistry
Краткое описание
N,O-Diprotonated forms (dications) of various quinolinecarbaldehydes were theoretically studied by DFT calculations. It was found that the most reactive electrophilic dications are expected to be generated from 2- and 4-quinolinecarbaldehydes compared to the other quinolinecarbaldehydes. Experimental studies of protonation of quinoline-2(6,8)-carbaldehydes in Brønsted acids (CF3SO3H, H2SO4) by means of 1H, 13C, and 15N NMR revealed the formation of the corresponding N-protonated O-protosolvated species. Reactions of quinoline-2(6,8)-carbaldehydes with arenes in the presence of Brønsted (TfOH) and Lewis acids (AlX3, X = Cl, Br) or acidic zeolites led to the formation of the corresponding 2(6,8)-(diarylmethyl)quinolines. However, 6- and 8-quinolinecarbaldehydes gave additionally unusual products – 6(8)-(arylmethyl)quinolines.
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Borisova M. А. et al. Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 10. pp. 1007-1016.
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Borisova M. А., Ryabukhin D. S., Ivanov A. Yu., Boyarskaya I. A., Spiridonova D. V., Kompanets M. O., Vasilyev A. V. Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 10. pp. 1007-1016.
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TY - JOUR
DO - 10.1007/s10593-021-03015-0
UR - https://doi.org/10.1007/s10593-021-03015-0
TI - Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species
T2 - Chemistry of Heterocyclic Compounds
AU - Borisova, Marina А
AU - Ryabukhin, Dmitry S
AU - Ivanov, Alexander Yu
AU - Boyarskaya, Irina A
AU - Spiridonova, Darya V
AU - Kompanets, Mikhail O
AU - Vasilyev, Aleksander V
PY - 2021
DA - 2021/10/29
PB - Springer Nature
SP - 1007-1016
IS - 10
VL - 57
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2021_Borisova,
author = {Marina А Borisova and Dmitry S Ryabukhin and Alexander Yu Ivanov and Irina A Boyarskaya and Darya V Spiridonova and Mikhail O Kompanets and Aleksander V Vasilyev},
title = {Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species},
journal = {Chemistry of Heterocyclic Compounds},
year = {2021},
volume = {57},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1007/s10593-021-03015-0},
number = {10},
pages = {1007--1016},
doi = {10.1007/s10593-021-03015-0}
}
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Borisova, Marina А., et al. “Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species.” Chemistry of Heterocyclic Compounds, vol. 57, no. 10, Oct. 2021, pp. 1007-1016. https://doi.org/10.1007/s10593-021-03015-0.
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