Synthesis of Atropisomeric Quinazolin-4-one Derivatives Based on Remote H/D and <sup>12</sup>C/<sup>13</sup>C Discrimination
Both enantiomers of 2-ethylquinazolin-4-ones bearing <i>ortho</i>-CH<sub>3</sub>O/CD<sub>3</sub>O and CH<sub>3</sub>O/<sup>13</sup>CH<sub>3</sub>O phenyl groups at the N3 position were prepared. These are isotopic atropisomeric compounds based on a remote and conformationally flexible H/D and <sup>12</sup>C/<sup>13</sup>C discrimination, and it was found that a CHCl<sub>3</sub> solution of <i>ortho</i>-CH<sub>3</sub>O/CD<sub>3</sub>O 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 <sup>1</sup>H NMR and chiral high-performance liquid chromatography (HPLC) analyses.
Authors
- Osamu Kitagawa (ORCID: https://orcid.org/0000-0001-7964-1879)
- Ryunosuke Senda
- Azusa Sato (ORCID: https://orcid.org/0000-0003-3347-4205)
- Yuka Watanabe (ORCID: https://orcid.org/0009-0001-8589-5127)
- Utae Take
Institutions
- Tokyo University of Pharmacy and Life Sciences (JP)
- Shibaura Institute of Technology (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-27
- DOI
- https://doi.org/10.1021/acs.joc.4c02772
- Citations
- 2
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Nagase Science Technology Foundation