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Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles : Theoretical Study. / Antonov, Alexander S.; Tupikina, Elena Yu; Karpov, Valerii V.; Mulloyarova, Valeriia V.; Bardakov, Victor G.

в: Molecules (Basel, Switzerland), Том 25, № 24, 17.12.2020.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Antonov, AS, Tupikina, EY, Karpov, VV, Mulloyarova, VV & Bardakov, VG 2020, 'Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles: Theoretical Study', Molecules (Basel, Switzerland), Том. 25, № 24. https://doi.org/10.3390/molecules25245977

APA

Antonov, A. S., Tupikina, E. Y., Karpov, V. V., Mulloyarova, V. V., & Bardakov, V. G. (2020). Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles: Theoretical Study. Molecules (Basel, Switzerland), 25(24). https://doi.org/10.3390/molecules25245977

Vancouver

Antonov AS, Tupikina EY, Karpov VV, Mulloyarova VV, Bardakov VG. Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles: Theoretical Study. Molecules (Basel, Switzerland). 2020 Дек. 17;25(24). https://doi.org/10.3390/molecules25245977

Author

Antonov, Alexander S. ; Tupikina, Elena Yu ; Karpov, Valerii V. ; Mulloyarova, Valeriia V. ; Bardakov, Victor G. / Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles : Theoretical Study. в: Molecules (Basel, Switzerland). 2020 ; Том 25, № 24.

BibTeX

@article{d0fb7d19c7e144e7bfcf7702a7476043,
title = "Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles: Theoretical Study",
abstract = "The influence of steric repulsion between the NMe2 group and a second ortho-(peri-)substituent in the series of 1-dimethylaminonaphthalene and N,N-dimethylanilene ortho-oximes on the ease of the NMe2 group's intramolecular nucleophilic substitution is studied. Possible reaction intermediates for three mechanisms are calculated (ωB97xd/def-2-TZVP), and their free Gibbs energies are compared to model reaction profiles. Supporting experiments have proved the absence of studied reactivity in the case of simple 2-dimethylaminobenzaldoxime, which allowed us to establish reactivity limits. The significant facilitation of NMe2 group displacement in the presence of bulky substituents is demonstrated. The possibility of fused isoxazoles synthesis via the intramolecular nucleophilic substitution of a protonated NMe2 group in the aniline and naphthalene series is predicted.",
keywords = "heterocyclization, isoxazole, nucleophilic substitution, quantum chemical calculations",
author = "Antonov, {Alexander S.} and Tupikina, {Elena Yu} and Karpov, {Valerii V.} and Mulloyarova, {Valeriia V.} and Bardakov, {Victor G.}",
note = "Copyright: This record is sourced from MEDLINE/PubMed, a database of the U.S. National Library of Medicine",
year = "2020",
month = dec,
day = "17",
doi = "10.3390/molecules25245977",
language = "English",
volume = "25",
journal = "Molecules",
issn = "1420-3049",
publisher = "MDPI AG",
number = "24",

}

RIS

TY - JOUR

T1 - Sterically Facilitated Intramolecular Nucleophilic NMe2 Group Substitution in the Synthesis of Fused Isoxazoles

T2 - Theoretical Study

AU - Antonov, Alexander S.

AU - Tupikina, Elena Yu

AU - Karpov, Valerii V.

AU - Mulloyarova, Valeriia V.

AU - Bardakov, Victor G.

N1 - Copyright: This record is sourced from MEDLINE/PubMed, a database of the U.S. National Library of Medicine

PY - 2020/12/17

Y1 - 2020/12/17

N2 - The influence of steric repulsion between the NMe2 group and a second ortho-(peri-)substituent in the series of 1-dimethylaminonaphthalene and N,N-dimethylanilene ortho-oximes on the ease of the NMe2 group's intramolecular nucleophilic substitution is studied. Possible reaction intermediates for three mechanisms are calculated (ωB97xd/def-2-TZVP), and their free Gibbs energies are compared to model reaction profiles. Supporting experiments have proved the absence of studied reactivity in the case of simple 2-dimethylaminobenzaldoxime, which allowed us to establish reactivity limits. The significant facilitation of NMe2 group displacement in the presence of bulky substituents is demonstrated. The possibility of fused isoxazoles synthesis via the intramolecular nucleophilic substitution of a protonated NMe2 group in the aniline and naphthalene series is predicted.

AB - The influence of steric repulsion between the NMe2 group and a second ortho-(peri-)substituent in the series of 1-dimethylaminonaphthalene and N,N-dimethylanilene ortho-oximes on the ease of the NMe2 group's intramolecular nucleophilic substitution is studied. Possible reaction intermediates for three mechanisms are calculated (ωB97xd/def-2-TZVP), and their free Gibbs energies are compared to model reaction profiles. Supporting experiments have proved the absence of studied reactivity in the case of simple 2-dimethylaminobenzaldoxime, which allowed us to establish reactivity limits. The significant facilitation of NMe2 group displacement in the presence of bulky substituents is demonstrated. The possibility of fused isoxazoles synthesis via the intramolecular nucleophilic substitution of a protonated NMe2 group in the aniline and naphthalene series is predicted.

KW - heterocyclization

KW - isoxazole

KW - nucleophilic substitution

KW - quantum chemical calculations

UR - http://www.scopus.com/inward/record.url?scp=85098927079&partnerID=8YFLogxK

U2 - 10.3390/molecules25245977

DO - 10.3390/molecules25245977

M3 - Article

C2 - 33348591

AN - SCOPUS:85098927079

VL - 25

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

ER -

ID: 73058552