Catalyst and additive-free oxidative dual C-H sulfenylation of imidazoheterocycles with elemental sulfur using DMSO as a solvent and an oxidant.

Dual C-H sulfenylation was used to obtain 3-vulcanized imidazoheterocycles using odorless elemental sulfur under catalyst- and additive-free conditions. C-H activation of both imidazoheterocycles and arylamines/arenols/indoles was realized by a practical protocol in which DMSO served as both a solvent and an internal oxidant.

Copper-catalyzed chalcogenation of imidazoheterocycles with sulfur/selenium powder and coumarinyl triflates.

An efficient and convenient copper-catalyzed chalcogenation of imidazoheterocycles with sulfur/selenium powder and coumarinyl triflates has been described. This procedure provides a wide range of structurally diverse coumarinylthio-/coumarinylseleno-substituted imidazoheterocycles in good yields and with good functional group tolerance. Biological evaluation showed that the newly synthesized compound 6d possesses significant in vitro antiproliferative activities against human-derived esophageal, breast, stomach, and prostate cancer cell lines compared with the positive control, 5-fluorouracil.