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
53
発行部数33
DOI
出版物ステータスPublished - 2012 8 15

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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