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Molbank 2017, 2017(1), M924; doi:10.3390/M924

(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one

1
Department of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, Colombia
2
WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
*
Author to whom correspondence should be addressed.
Academic Editor: René T. Boeré
Received: 1 December 2016 / Revised: 23 December 2016 / Accepted: 28 December 2016 / Published: 30 December 2016
(This article belongs to the Section Structure Determination)
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Abstract

The title chalcone (E)-1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one was obtained in 76% yield from a NaOH catalyzed Claisen–Schmidt condensation reaction between o-aminoacetophenone and piperonal. This product will be used as a key precursor for the development of an alternative route for the total synthesis of the alkaloid Graveoline. 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. The crystal structure of the title o-aminochalcone, C16H13NO3, shows two molecules per asymmetric unit (Z = 4) 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 follow: [root-mean-square (r.m.s.) deviation = 0.0210 Å for A–B and 0.0493 for C–D molecules]. In the crystal, molecules are linked by N–H...O and C–H...O, hydrogen bonds forming S(6), R22(6) and edge-fused R44(24)rings along with C(18) chains running parallel to (110). View Full-Text
Keywords: o-aminoacetophenones; benzodioxolyl moiety; Claisen–Schmidt condensation; o-aminochalcones; single crystal X-ray diffraction o-aminoacetophenones; benzodioxolyl moiety; Claisen–Schmidt condensation; o-aminochalcones; single crystal X-ray diffraction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Abonia, R.; Arteaga, D.; Insuasty, D.; Quiroga, J.; Insuasty, B.; Moreno-Fuquen, R.; Kennedy, A.R. (E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one. Molbank 2017, 2017, M924.

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