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DOI: 10.1055/a-1874-5283
Base-Catalyzed Synthesis of Flavones via Thiol-Assisted Sequential Demethylation/Cyclization of 1-(2-Methoxyphenyl)prop-2-yn-1-ones
We are grateful to Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS 19/2551-0001947-5), and Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq-Universal 428193/2018-8). This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brazil (CAPES) - Finance Code 001.
Abstract
Flavone and analogues represent an important class of biologically and pharmacologically active substances commonly found in the composition of diverse plants as part of the class of secondary metabolites. Herein, an efficient and regioselective synthetic strategy for the preparation of functionalized flavones is demonstrated through sequential demethylation/6-endo-dig intramolecular cyclization of propyn-1-ones, using catalytic amounts of base in the presence of a thiol, by employing NMP as the solvent. The reactions proceeded smoothly under transition-metal-free and open to air conditions, furnishing the desired six-membered heterocycles in moderate to excellent yields, in short reaction time.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1874-5283.
- Supporting Information
Publication History
Received: 03 March 2022
Accepted after revision: 13 June 2022
Accepted Manuscript online:
13 June 2022
Article published online:
20 July 2022
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