Studies on rotational stability of 2-aryl-3-(2-fluorophenyl)quinazolin-4-one derivatives

Asumi Iida; Kazuya Saito; Nanami Asada; Yuuki Fujimoto; Osamu Kitagawa

doi:10.3987/COM-20-S(K)10

Studies on rotational stability of 2-aryl-3-(2-fluorophenyl)quinazolin-4-one derivatives

Asumi Iida, Kazuya Saito, Nanami Asada, Yuuki Fujimoto, Osamu Kitagawa

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

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Abstract

The rotational barriers around an N-(2-F)C₆H₄ bond in 2-aryl-3-(2-fluorophenyl)quinazolin-4-ones considerably lowered (ca. 4 kcal mol^-1 lower) in comparison with those of 2-alkyl-3-(2-fluorophenyl)quinazolin-4-ones. The transition state structure estimated by the DFT calculation indicates that the considerable decrease in the rotational barriers in 2-aryl derivatives is caused by the alleviation of the steric repulsion between an ortho-substituent of 2-fluorophenyl group and 2-aryl group.

Original language	English
Journal	Heterocycles
Volume	103
Issue number	1
DOIs	https://doi.org/10.3987/COM-20-S(K)10
Publication status	Published - 2021

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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title = "Studies on rotational stability of 2-aryl-3-(2-fluorophenyl)quinazolin-4-one derivatives",

abstract = "The rotational barriers around an N-(2-F)C6H4 bond in 2-aryl-3-(2-fluorophenyl)quinazolin-4-ones considerably lowered (ca. 4 kcal mol-1 lower) in comparison with those of 2-alkyl-3-(2-fluorophenyl)quinazolin-4-ones. The transition state structure estimated by the DFT calculation indicates that the considerable decrease in the rotational barriers in 2-aryl derivatives is caused by the alleviation of the steric repulsion between an ortho-substituent of 2-fluorophenyl group and 2-aryl group.",

author = "Asumi Iida and Kazuya Saito and Nanami Asada and Yuuki Fujimoto and Osamu Kitagawa",

note = "Funding Information: We would like to thank Prof. Christian Roussel for useful discussions. This work was partly supported by JSPS KAKENNHI (C 20K06945). Publisher Copyright: {\textcopyright} 2021 Japan Institute of Heterocyclic Chemistry. All rights reserved.",

year = "2021",

doi = "10.3987/COM-20-S(K)10",

language = "English",

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T1 - Studies on rotational stability of 2-aryl-3-(2-fluorophenyl)quinazolin-4-one derivatives

AU - Iida, Asumi

AU - Saito, Kazuya

AU - Asada, Nanami

AU - Fujimoto, Yuuki

AU - Kitagawa, Osamu

N1 - Funding Information: We would like to thank Prof. Christian Roussel for useful discussions. This work was partly supported by JSPS KAKENNHI (C 20K06945). Publisher Copyright: © 2021 Japan Institute of Heterocyclic Chemistry. All rights reserved.

PY - 2021

Y1 - 2021

N2 - The rotational barriers around an N-(2-F)C6H4 bond in 2-aryl-3-(2-fluorophenyl)quinazolin-4-ones considerably lowered (ca. 4 kcal mol-1 lower) in comparison with those of 2-alkyl-3-(2-fluorophenyl)quinazolin-4-ones. The transition state structure estimated by the DFT calculation indicates that the considerable decrease in the rotational barriers in 2-aryl derivatives is caused by the alleviation of the steric repulsion between an ortho-substituent of 2-fluorophenyl group and 2-aryl group.

AB - The rotational barriers around an N-(2-F)C6H4 bond in 2-aryl-3-(2-fluorophenyl)quinazolin-4-ones considerably lowered (ca. 4 kcal mol-1 lower) in comparison with those of 2-alkyl-3-(2-fluorophenyl)quinazolin-4-ones. The transition state structure estimated by the DFT calculation indicates that the considerable decrease in the rotational barriers in 2-aryl derivatives is caused by the alleviation of the steric repulsion between an ortho-substituent of 2-fluorophenyl group and 2-aryl group.

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Studies on rotational stability of 2-aryl-3-(2-fluorophenyl)quinazolin-4-one derivatives

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