Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species

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Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species. / Borisova, Marina; Ryabukhin, Dmitry S.; Ivanov, Alexander Yu; Boyarskaya, Irina A.; Spiridonova, Dar’ya V.; Kompanets, Mikhail O.; Vasilyev, Aleksander V.

In: Chemistry of Heterocyclic Compounds, Vol. 57, No. 10, 29.10.2021, p. 1007-1016.

Research output: Contribution to journal › Article › peer-review

Author

Borisova, Marina ; Ryabukhin, Dmitry S. ; Ivanov, Alexander Yu ; Boyarskaya, Irina A. ; Spiridonova, Dar’ya V. ; Kompanets, Mikhail O. ; Vasilyev, Aleksander V. / Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species. In: Chemistry of Heterocyclic Compounds. 2021 ; Vol. 57, No. 10. pp. 1007-1016.

BibTeX

@article{51f765b9d09d4608ab4efe66557123d6,

title = "Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species",

abstract = "[Figure not available: see fulltext.] 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 Br{\o}nsted 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 Br{\o}nsted (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.",

keywords = "carbocations, DFT calculations, Friedel–Crafts reaction, quinolines, superelectrophilic activation, QUINOLINE, ACIDS, CONDENSATION, INHIBITORS, DERIVATIVES, Friedel-Crafts reaction, HYDRIDE TRANSFER",

author = "Marina Borisova and Ryabukhin, {Dmitry S.} and Ivanov, {Alexander Yu} and Boyarskaya, {Irina A.} and Spiridonova, {Dar{\textquoteright}ya V.} and Kompanets, {Mikhail O.} and Vasilyev, {Aleksander V.}",

note = "Publisher Copyright: {\textcopyright} 2021, Springer Science+Business Media, LLC, part of Springer Nature.",

year = "2021",

month = oct,

day = "29",

doi = "10.1007/s10593-021-03015-0",

language = "English",

volume = "57",

pages = "1007--1016",

journal = "Chemistry of Heterocyclic Compounds",

issn = "0009-3122",

publisher = "Springer Nature",

number = "10",

}

RIS

TY - JOUR

T1 - Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species

AU - Borisova, Marina

AU - Ryabukhin, Dmitry S.

AU - Ivanov, Alexander Yu

AU - Boyarskaya, Irina A.

AU - Spiridonova, Dar’ya V.

AU - Kompanets, Mikhail O.

AU - Vasilyev, Aleksander V.

PY - 2021/10/29

Y1 - 2021/10/29

N2 - [Figure not available: see fulltext.] 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.

AB - [Figure not available: see fulltext.] 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.

KW - carbocations

KW - DFT calculations

KW - Friedel–Crafts reaction

KW - quinolines

KW - superelectrophilic activation

KW - QUINOLINE

KW - ACIDS

KW - CONDENSATION

KW - INHIBITORS

KW - DERIVATIVES

KW - Friedel-Crafts reaction

KW - HYDRIDE TRANSFER

UR - http://www.scopus.com/inward/record.url?scp=85118214667&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/66a9d5cb-88ac-3a9c-812c-f11e44d911f7/

U2 - 10.1007/s10593-021-03015-0

DO - 10.1007/s10593-021-03015-0

M3 - Article

AN - SCOPUS:85118214667

VL - 57

SP - 1007

EP - 1016

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 10

ER -

ID: 87957623