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Updated: May 13, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
1-{(Z)-[(2,3-Dihy-droxy-prop-yl)amino]-methyl-idene}naphthalen-2(1H)-one
Mehmet Akkurt1, Peter N Horton, Shaaban K Mohamed
1Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
Abstract:
In the title mol-ecule, C14H15NO3, the ring system is essentially planar, with an r.m.s. deviation of 0.003 Å. The atoms of the ethane-1,2-diol group were refined as disordered over two sets of sites in a ratio of 0.815 (3):0.185 (3). The mol-ecular conformation is stabilized in part by an intra-molecular N-H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, mol-ecules are connected by N-H⋯O and O-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). The network also features weak C-H⋯O hydrogen bonds. Weak C-H⋯π inter-actions also observed.
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