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5-[(Z)-5-Chloro-2-oxoindolin-3-ylidene]-3-{(E)-[(4-hydroxyphenyl)imino]methyl}-2-thioxothiazolidin-4-one

1
Laboratoire de synthèse organique appliquée, université oran1-Ahmed Benbella, Algeria. Bp 1524 el m’naouer, Oran 31000, Algeria
2
Université des Sciences et de la Technologie d’Oran Mohamed-Boudiaf El Mnaouar, BP 1505, Bir El Djir, Oran 31000, Algeria
*
Author to whom correspondence should be addressed.
Molbank 2019, 2019(2), M1059; https://doi.org/10.3390/M1059
Received: 6 April 2019 / Revised: 4 May 2019 / Accepted: 6 May 2019 / Published: 6 May 2019
(This article belongs to the Special Issue Molecules from Multicomponent Reactions)
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Abstract

N-aminorhodanine as well as isatin are highly solicited motifs known for their wide potential for biological activity. The objective of this work was to synthesize hybrid molecules as kinase inhibitors from these two motifs. In order to study the reactivity of the two active centers in aminorhodanine (N-amino group and the 5-methylene group) toward two carbonyl groups (aromatic aldehyde and ketone of isatin), we decided to carry out a one-pot multi-component reaction by simultaneously introducing aminorhodanine, isatin, and an aromatic aldehyde in ethanol in the presence of AcOEt. Under these conditions, this reaction led to a single adduct. The reaction product structure was confirmed by 1H, 13C-NMR, X-ray single crystal analysis, and high-resolution mass HRMS analysis. As a result, the method used has been very effective and totally stereo- and regioselective. View Full-Text
Keywords: N-aminorhodanine; isatin; hybrid-molecules; Knoevenagel; Schiff’s bases; multi-component reactions N-aminorhodanine; isatin; hybrid-molecules; Knoevenagel; Schiff’s bases; multi-component reactions
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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Safer, A.; Khaldoun, K.; Saidi-Besbes, S. 5-[(Z)-5-Chloro-2-oxoindolin-3-ylidene]-3-{(E)-[(4-hydroxyphenyl)imino]methyl}-2-thioxothiazolidin-4-one. Molbank 2019, 2019, M1059.

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