4.6 Article

Synthesis of Novel 1,4-Diketone Derivatives and Their Further Cyclization

Journal

ACS OMEGA
Volume 8, Issue 15, Pages 14047-14052

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acsomega.3c00610

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In this study, new derivatives (substituted arenoxy) of 1,4-diketone compounds were synthesized using a new version of the Stetter reaction method. The reaction was catalyzed by 3benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, with triethylamine as the basic medium and dimethyl sulfoxide as the solvent. Some novel arenoxy-substituted 1,4-diketones were obtained with good yields at room temperature within 24 hours through an intermolecular Stetter reaction.
One of the important reactions to obtain a new carbon-carbon bond is the Stetter reaction, which is generally via a nucleophilic catalyst like cyanide or thiazolium-NHC catalysts. In particular, 1,4-diketones with very functional properties are obtained by the Stetter reaction with the intermolecular reaction of an aldehyde and an alpha,beta-unsaturated ketone. In this study, we synthesized new derivatives (substituted arenoxy) of 1,4-diketone compounds (2a-2n) with useful features by a new version of the Stetter reaction method. In our work, arenoxy benzaldehyde derivatives with different structures as the Michael donor and methyl vinyl ketone as the Michael acceptor were used for the intermolecular Stetter reaction. The reaction was catalyzed by 3benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride (3b), using triethylamine for the basic medium and dimethyl sulfoxide as the solvent. As a result, some novel arenoxy-substituted 1,4-diketones were gained with good yields at room temperature within 24 h through an intermolecular Stetter reaction. In addition, new furan and pyrrole derivatives were prepared by performing the cyclization reaction with one of the obtained new diketone compounds.

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