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Copper-Catalyzed Cascade 1,4-Addition/Annulation/Hydrolysis of Propargylamines with 2-Hydroxynaphthalene-1,4-diones: Direct Formation of 12-Phenacyl-11-benzo[]xanthenes. | LitMetric

Copper-Catalyzed Cascade 1,4-Addition/Annulation/Hydrolysis of Propargylamines with 2-Hydroxynaphthalene-1,4-diones: Direct Formation of 12-Phenacyl-11-benzo[]xanthenes.

J Org Chem

Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. China.

Published: March 2021

A novel and versatile approach to construct 12-phenacyl-11-benzo[]xanthene-6,11(12)-dione derivatives through copper-catalyzed cascade reaction of propargylamines with 2-hydroxynaphthalene-1,4-diones has been developed. The procedure is proposed to go through a sequence of 1,4-conjugate addition, intramolecular nucleophilic addition/dehydration, and hydrolysis of alkyne followed by an enol-ketone tautomerization. The reaction provides a new and highly efficient method for the synthesis of 12-phenacyl-11-benzo[]xanthene-6,11(12)-diones by formation of three new bonds and one heterocycle from readily available starting materials in good to high yields (70-88%) with broad functional group compatibility in a single step.

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Source
http://dx.doi.org/10.1021/acs.joc.0c03029DOI Listing

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