Studies on rotational barriers of N-C axially chiral compounds: Increase in the rotational barrier by aromatization

Naomi Suzumura; Masato Kageyama; Daichi Kamimura; Takahiro Inagaki; Yasuo Dobashi; Hiroshi Hasegawa; Haruhiko Fukaya; Osamu Kitagawa

doi:10.1016/j.tetlet.2012.06.007

Studies on rotational barriers of N-C axially chiral compounds: Increase in the rotational barrier by aromatization

Naomi Suzumura, Masato Kageyama, Daichi Kamimura, Takahiro Inagaki, Yasuo Dobashi, Hiroshi Hasegawa, Haruhiko Fukaya, Osamu Kitagawa

研究成果: Article

10 引用（Scopus）

抜粋

The rotational barriers in axially chiral quinolin-2-one and quinazolin-2-one possessing N-(ortho-tert-butyl)phenyl group were found to significantly increase in comparison with those of corresponding dihydroquinolin-2-one and dihydroquinazolin-2-one. Analysis of transition state structure during N-Ar bond rotation based on DFT calculation indicates that the increase in the rotational barrier is due to considerable distortion of the nitrogen-containing heterocyclic part.

元の言語	English
ページ（範囲）	4332-4336
ページ数	5
ジャーナル	Tetrahedron Letters
巻	53
発行部数	33
DOI	https://doi.org/10.1016/j.tetlet.2012.06.007
出版物ステータス	Published - 2012 8 15

フィンガープリント

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

これを引用

Suzumura, N., Kageyama, M., Kamimura, D., Inagaki, T., Dobashi, Y., Hasegawa, H., Fukaya, H., & Kitagawa, O. (2012). Studies on rotational barriers of N-C axially chiral compounds: Increase in the rotational barrier by aromatization. Tetrahedron Letters, 53(33), 4332-4336. https://doi.org/10.1016/j.tetlet.2012.06.007

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abstract = "The rotational barriers in axially chiral quinolin-2-one and quinazolin-2-one possessing N-(ortho-tert-butyl)phenyl group were found to significantly increase in comparison with those of corresponding dihydroquinolin-2-one and dihydroquinazolin-2-one. Analysis of transition state structure during N-Ar bond rotation based on DFT calculation indicates that the increase in the rotational barrier is due to considerable distortion of the nitrogen-containing heterocyclic part.",

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T1 - Studies on rotational barriers of N-C axially chiral compounds

T2 - Increase in the rotational barrier by aromatization

AU - Suzumura, Naomi

AU - Kageyama, Masato

AU - Kamimura, Daichi

AU - Inagaki, Takahiro

AU - Dobashi, Yasuo

AU - Hasegawa, Hiroshi

AU - Fukaya, Haruhiko

AU - Kitagawa, Osamu

PY - 2012/8/15

Y1 - 2012/8/15

N2 - The rotational barriers in axially chiral quinolin-2-one and quinazolin-2-one possessing N-(ortho-tert-butyl)phenyl group were found to significantly increase in comparison with those of corresponding dihydroquinolin-2-one and dihydroquinazolin-2-one. Analysis of transition state structure during N-Ar bond rotation based on DFT calculation indicates that the increase in the rotational barrier is due to considerable distortion of the nitrogen-containing heterocyclic part.

AB - The rotational barriers in axially chiral quinolin-2-one and quinazolin-2-one possessing N-(ortho-tert-butyl)phenyl group were found to significantly increase in comparison with those of corresponding dihydroquinolin-2-one and dihydroquinazolin-2-one. Analysis of transition state structure during N-Ar bond rotation based on DFT calculation indicates that the increase in the rotational barrier is due to considerable distortion of the nitrogen-containing heterocyclic part.

KW - Aromatization

KW - Axially chiral

KW - Quinazolinone

KW - Quinolinone

KW - Rotational barrier

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DO - 10.1016/j.tetlet.2012.06.007

M3 - Article

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JO - Tetrahedron Letters

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文献にアクセス

10.1016/j.tetlet.2012.06.007