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 journalArticle

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

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Aromatization
Discrete Fourier transforms
Nitrogen

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Studies on rotational barriers of N-C axially chiral compounds : Increase in the rotational barrier by aromatization. / Suzumura, Naomi; Kageyama, Masato; Kamimura, Daichi; Inagaki, Takahiro; Dobashi, Yasuo; Hasegawa, Hiroshi; Fukaya, Haruhiko; Kitagawa, Osamu.

In: Tetrahedron Letters, Vol. 53, No. 33, 15.08.2012, p. 4332-4336.

Research output: Contribution to journalArticle

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, vol. 53, no. 33, pp. 4332-4336. https://doi.org/10.1016/j.tetlet.2012.06.007
Suzumura, Naomi ; Kageyama, Masato ; Kamimura, Daichi ; Inagaki, Takahiro ; Dobashi, Yasuo ; Hasegawa, Hiroshi ; Fukaya, Haruhiko ; Kitagawa, Osamu. / Studies on rotational barriers of N-C axially chiral compounds : Increase in the rotational barrier by aromatization. In: Tetrahedron Letters. 2012 ; Vol. 53, No. 33. pp. 4332-4336.
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