Abstract
The title chalcone (E)-1-(2-aminophenyl)-3-(4-chlorophenyl)prop-2-en-1-one was prepared with an excellent yield from a Claisen–Schmidt condensation reaction between o-aminoacetophenone and p-chlorobenzaldehyde. This product will be used as a key precursor for the development of an alternative route for the total synthesis of dubamine and graveoline alkaloids. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure and determine some interesting supramolecular properties. The crystal structure of the title o-aminochalcone, C15H12ClNO, shows two molecules per asymmetric unit (Z′ = 2) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follows: [r.m.s. deviation = 0.0130 Å for A-B and 0.0043 for C-D molecules]. In the crystal, molecules are linked by N—H...N and C—H...O, hydrogen bonds forming edge-fused R66(46) rings parallel to (100). Additionally, N—H...O hydrogen bonds generate a three-dimensional network.
Highlights
Chalcones are synthetic or naturally occurring α,β-unsaturated diaryl ketones which have shown a wide spectrum of biological activities as anti-tubercular [1], anti-inflammatory [2], antimalarial [3], antibacterial [4], antifungal [5], and mainly antitumor agents [6]. These compounds have been widely used as precursors for diverse synthetic approaches, mainly in the synthesis of hererocyclic compounds [7,8]
Our studies are focused in developing an alternative straightforward approach for the total synthesis of dubamine and graveoline alkaloids starting from a common quinolone precursor
O-aminochalcones were visualized as key precursors for our goals
Summary
Chalcones are synthetic or naturally occurring α,β-unsaturated diaryl ketones which have shown a wide spectrum of biological activities as anti-tubercular [1], anti-inflammatory [2], antimalarial [3], antibacterial [4], antifungal [5], and mainly antitumor agents [6] These compounds have been widely used as precursors for diverse synthetic approaches, mainly in the synthesis of hererocyclic compounds [7,8]. In this sense, and continuing with our current studies on the synthetic utility of o-aminochalcones [9,10], the amino-derivative 3, and analogues, were obtained from the condensation reaction of o-aminoacetophenone 1 and p-chlorobenzaldehyde 2 (Scheme 1) to be subsequently transformed into heterocyclic alkaloids of biological interest
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