Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

Yuya Suzuki; Isao Takahashi; Yasuo Dobashi; Hiroshi Hasegawa; Christian Roussel; Osamu Kitagawa

doi:10.1016/j.tetlet.2014.11.040

Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

Yuya Suzuki, Isao Takahashi, Yasuo Dobashi, Hiroshi Hasegawa, Christian Roussel, Osamu Kitagawa

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

10 Citations (Scopus)

Abstract

The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and ¹H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.

Original language	English
Pages (from-to)	132-135
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2014.11.040
Publication status	Published - 2015 Jan 1

Keywords

Amination
Axially chiral
Distortion
Quinolinone
Rotational barrier

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2014.11.040

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title = "Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one",

abstract = "The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.",

keywords = "Amination, Axially chiral, Distortion, Quinolinone, Rotational barrier",

author = "Yuya Suzuki and Isao Takahashi and Yasuo Dobashi and Hiroshi Hasegawa and Christian Roussel and Osamu Kitagawa",

year = "2015",

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T1 - Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

AU - Suzuki, Yuya

AU - Takahashi, Isao

AU - Dobashi, Yasuo

AU - Hasegawa, Hiroshi

AU - Roussel, Christian

AU - Kitagawa, Osamu

PY - 2015/1/1

Y1 - 2015/1/1

N2 - The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.

AB - The rotational barrier around the N-C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6 kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.

KW - Amination

KW - Axially chiral

KW - Distortion

KW - Quinolinone

KW - Rotational barrier

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Relationship between rotational barriers and structures in N-C axially chiral 3,4-dihydroquinolin-2-one and 3,4-dihydrobenzoquinolin-2-one

Abstract

Keywords

ASJC Scopus subject areas

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