Rotational Behavior about the N3–Pyridyl Bond in 3‑(Pyridin-2-yl)quinazolin-4-one and 4‑Thione Derivatives

The rotational barriers about the N3–(2-pyridyl) bond in 2-iso-propyl-3-(pyridin-2-yl)­quinazolin-4-one and the thione analogue were evaluated though VT-NMR measurement of a diastereotopic iso-propyl group followed by a line-shape simulation. In 3-(pyridin-2-yl)­quinazoline-4-thione bearing a chiral...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-08, Vol.89 (15), p.11072-11077
Main Authors: Wang, Yuxiang, Yang, Yue, Homma, Daiki, Caytan, Elsa, Roussel, Christian, Sato, Azusa, Yanai, Hikaru, Kitagawa, Osamu
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary:The rotational barriers about the N3–(2-pyridyl) bond in 2-iso-propyl-3-(pyridin-2-yl)­quinazolin-4-one and the thione analogue were evaluated though VT-NMR measurement of a diastereotopic iso-propyl group followed by a line-shape simulation. In 3-(pyridin-2-yl)­quinazoline-4-thione bearing a chiral center as the C2 substituent, the formation of dynamic diastereomers was detected by NMR. The rotational pathway about the N3–(2-pyridyl) bond and the stereochemistries of dynamic diastereomers were revealed through a computational study.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01186