Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 5, Pages 4182-4192Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c03029
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Funding
- Anhui Provincial Natural Science Foundation [1808085MB41]
- National Natural Science Foundation of China [21772001]
- Cultivation Project for University Outstanding Talents of Anhui Province
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A novel and versatile approach has been developed for the construction of 12-phenacyl-11H-benzo[b]xanthene-6,11(12H)-dione derivatives through a copper-catalyzed cascade reaction. This method provides a highly efficient synthesis of these derivatives in a single step from readily available starting materials, forming new bonds and a heterocycle.
A novel and versatile approach to construct 12-phenacyl-11H-benzo[b]xanthene-6,11(12H)-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-11H-benzo[b]xanthene-6,11(12H)-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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