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

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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.

Original languageEnglish
Pages (from-to)4332-4336
Number of pages5
JournalTetrahedron Letters
Volume53
Issue number33
DOIs
Publication statusPublished - 2012 Aug 15

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Keywords

  • Aromatization
  • Axially chiral
  • Quinazolinone
  • Quinolinone
  • Rotational barrier

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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