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

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

17 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4332-4336
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2012.06.007
Publication status	Published - 2012 Aug 15

Keywords

Aromatization
Axially chiral
Quinazolinone
Quinolinone
Rotational barrier

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.06.007

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

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.",

keywords = "Aromatization, Axially chiral, Quinazolinone, Quinolinone, Rotational barrier",

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

note = "Funding Information: This work was partly supported by a Grant-in-Aid (C22590015) for Scientific Research and the Ministry of Education, Science, Sports, and Culture of Japan. ",

year = "2012",

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doi = "10.1016/j.tetlet.2012.06.007",

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journal = "Tetrahedron Letters",

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TY - JOUR

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

N1 - Funding Information: This work was partly supported by a Grant-in-Aid (C22590015) for Scientific Research and the Ministry of Education, Science, Sports, and Culture of Japan.

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

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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