Article Dans Une Revue Journal of Organic Chemistry Année : 2024

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

Résumé

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.
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hal-04690667 , version 1 (21-01-2025)

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Yuxiang Wang, Yue Yang, Daiki Homma, Elsa Caytan, Christian Roussel, et al.. Rotational Behavior about the N3–Pyridyl Bond in 3-(Pyridin-2-yl)quinazolin-4-one and 4-Thione Derivatives. Journal of Organic Chemistry, 2024, 89 (15), pp.11072-11077. ⟨10.1021/acs.joc.4c01186⟩. ⟨hal-04690667⟩
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