Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7- dimethylaminocoumarin

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Title:	Conformation and photochemical properties of 3-benzoyl-4-benzylamino-7- dimethylaminocoumarin
Authors:	Lin, C.-H., Chuang, R.-R., Kuo, P.-Y., Yang, D.-Y.
Contributors:	Department of Chemistry, Tunghai University
Keywords:	π-π Aromatic stacking;Coumarin;Intramolecular hydrogen bonding;Photooxidation
Date:	2013
Issue Date:	2013-05-14T09:02:11Z (UTC)
Abstract:	3-Benzoyl-4-benzylamino-7-dimethylaminocoumarin was synthesized and its conformation in solid state and solution was determined. While the X-ray crystal analysis showed an aromatic π-π stacking interaction in the solid state, the proton NMR studies suggested the presence of an intramolecular hydrogen bonding in solution. Adjacent functional group modifications through N-methylation, reduction of carbonyl group, or replacing the coumarin moiety to dimedone, all resulted in disrupting the π-π stacking conformation. Upon UV irradiation, the 7-methylamino group can be oxidized by molecular oxygen to the corresponding formamide in the absence of any external photosensitizers. ? 2013 Elsevier Ltd. All rights reserved.
Relation:	Tetrahedron Letters 54 (19) , pp. 2431-2434
Appears in Collections:	[Department of Chemistry ] Periodical Articles

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