Visible‐Light‐Promoted Synthesis of Arylthiopyrimidines through Oxidative Coupling of Pyrimidine Disulfides with Arylhydrazines

Abstract

This report describes the oxidative coupling reaction of dithiopyrimidines with phenylhydrazine hydrochlorides to synthesize a series of arylthiopyrimidine derivatives. The reaction does not require transition metals as catalysts, and uses organic dye rose bengal as photocatalyst and air as oxidant. The reaction conditions are mild and meet the requirements of green chemistry. In addition, the method has a wide scope of substrates and good tolerance of functional groups. The control experiment showed that the reaction may be a free radical mechanism, and the molecular weight of the intermediate was captured by high‐resolution mass spectrometry.

Radical coupling reactions of hydrazinesviaphotochemical and electrochemical strategies

“…26 After that, several similar oxidative coupling reactions of arylhydrazines with disulfides as sulfur source under visible light conditions were reported by Yu and Wang's group (Schemes 23 and 24), respectively. 28,29 A series of diaryl sulfides were obtained in moderated to good yields. The latter reaction exhibited excellent functional group compatibility, broad scope of substrates, scalability and mild conditions.…”