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Updated: Jun 4, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Synthesis of Atropisomeric Quinazolin-4-one Derivatives Based on Remote H/D and 12C/13C Discrimination
Yuka Watanabe1, Utae Take1, Ryunosuke Senda1
1Chemistry and Materials Program, College of Engineering, Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.
Abstract:
Both enantiomers of 2-ethylquinazolin-4-ones bearing ortho-CH3O/CD3O and CH3O/13CH3O phenyl groups at the N3 position were prepared. These are isotopic atropisomeric compounds based on a remote and conformationally flexible H/D and 12C/13C discrimination, and it was found that a CHCl3 solution of ortho-CH3O/CD3O derivative shows a slight specific optical rotation. Furthermore, diastereomeric quinazolinone derivatives bearing a chiral carbon were prepared, and their stereochemical purities and rotational stability as well as the isotopic atropisomerism were verified by 1H NMR and chiral high-performance liquid chromatography (HPLC) analyses.
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