Base-Catalyzed Synthesis of Flavones via Thiol-Assisted Sequential Demethylation/Cyclization of 1-(2-Methoxyphenyl)prop-2-yn-1-ones

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.