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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-[(E)-(2-Phenoxy-anilino)methyl-ene]naphthalen-2(1H)-one
Abstract:
The mol-ecule of the title compound, C(23)H(17)NO(2), a Schiff base derived from 2-hydr-oxy-1-naphthaldehyde, crystallizes in the keto-amine tautomeric form. The dihedral angle between the aniline and hydroxy-benzene rings is 77.41 (17)°, whereas the planes of the naphthaldehyde and fused aniline benzene rings are nearly coplanar, making a dihedral angle of 8.29 (15)°. Intra-molecular N-H⋯O hydrogen bonding, a characteristic hydrogen bond for Schiff bases, helps to stabilize the mol-ecular structure. Weak inter-molecular C-H⋯π inter-actions are present in the crystal structure.
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