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Updated: Jun 1, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
rac-2-Methyl-3,4,5,6-tetra-hydro-2H-2,6-methano-1,3-benzoxazocin-4-one
Viktor Kettmann1, Jan Světlík, Lucia Veizerová
1Faculty of Pharmacy, Comenius University, Odbojarov 10, SK-83232 Bratislava, Slovakia.
Abstract:
The title compound, C(12)H(13)NO(2), represents a conformationally restricted 2-pyridone analogue of 1,4-dihydro-pyridine-type calcium antagonists and was selected for a crystal structure determination in order to explore some aspects of drug-receptor inter-action. In the mol-ecule, two stereogenic centres are of opposite chirality, whereas a racemate occurs in the crystal. It was found that the formally aminic N atom of the heterocycle is essentially sp(2)-hybridized with the lone-pair electrons partially delocalized through conjugation with the adjacent carbonyl bond. As a result, the central pyridone ring assumes an unsymmetrical half-chair conformation. The critical 4-phenyl ring is fixed in a pseudo-axial and perpendicular orientation [dihedral angle 85.8 (1)°] with respect to the pyridone ring via an oxygen bridge. In the crystal a pair of centrosymmetric N-H⋯O hydrogen bonds connect mol-ecules of opposite chirality into a dimer. The dimers are packed by hydrophobic van der Waals inter-actions.
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