Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder

Abstract

New flavone derivatives are highly valued in drug discovery due to their diversity of important bioactivities. Herein, one simple Cu-catalyzed method of constructing C-Se bonds on flavone structures using convenient Se powder via C-H functionalization is reported, regioselectively affording ArSe-substituted flavone derivatives in good yields.

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

“…353 A different sulfenylation agent, potassium thiocyanate, was used in the synthesis of 3-S-(alkyl/aryl)-4H-chromen-4-ones starting from 2,3-unsubstituted chromen-4-ones and alkyl/aryl halides mediated by copper(I) cyanide in DMF. 354 Polysubstituted 3-arylseleno-4H-chromen-4-ones were prepared via direct CdH functionalization of 2,3-unsubstituted chromones with aryl halides, using potassium selenocyanate 354 and selenium powder 355 as selenation agents promoted respectively by copper(I) iodide and copper(I) cyanide, in DMF. An alternative regioselective selenation reaction employs dialkyl/diaryl diselenides promoted by N-iodosuccinimide (NIS) and TBHP in DMF to obtain 3-alkyl/arylseleno-4H-chromen-4-ones (Scheme 57).…”

Radical Aminoselenation of Styrenes: Facile Access to β-Amido-selenides

“…[7] The amino-selenation with alkyl amine, has not been realized, which may be due to the unstable activity of alkyl amines under oxidation conditions. With the rapidly development of organoselenium chemistry [9] and our ongoing interest in organoselenium involved reactions, [10] herein we report a general method for the high-efficiency synthesis of β-amido selenides via amidoselenation of alkenes with alkyl amines and various diselenides. Gram-scale synthesis shows the practicability of this reaction and its potential use in industrial applications.…”