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The catalytic role of elemental sulfur in the DMSO-promoted oxidative coupling of methylhetarenes with amines: synthesis of thioamides and bis-aza-heterocycles

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Thioamides could be conveniently synthesized in good to excellent yields via DMSO-promoted oxidative coupling of methylhetarenes with amines in the presence of a near stoichiometric amount of sulfur (1.25 equiv.).… Click to show full abstract

Thioamides could be conveniently synthesized in good to excellent yields via DMSO-promoted oxidative coupling of methylhetarenes with amines in the presence of a near stoichiometric amount of sulfur (1.25 equiv.). Both aliphatic and aromatic amines were found to be competent substrates. When anilines o-substituted by cyclizable groups such as OH, NH2, NHPh, SH and CONH2 were used as amine substrates, the corresponding hybrid bis-aza-heterocycles were formed in high yields even with a sulfur loading as low as 0.5 equiv.

Keywords: promoted oxidative; oxidative coupling; coupling methylhetarenes; methylhetarenes amines; dmso promoted; bis aza

Journal Title: Organic chemistry frontiers
Year Published: 2021

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