Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur
Citations Over TimeTop 13% of 2019 papers
Abstract
Dialkyl azo compounds were found to be effective alkyl radical sources for direct alkyl sulfuration with imidazopyridines using elemental sulfur under metal-free conditions. Iodine, an inexpensive and mild reagent, could promote alkyl sulfuration. A variety of quaternary cyanoalkyl radicals were successfully coupled with elemental sulfur. A subsequent C-H sulfuration of imidazopyridines afforded a diverse array of imidazopyridine derivatives bearing cyanoalkylthio groups. The cyano group could be modified and further underwent condensation with 2-aminothiazole to afford an interesting heterocyclic amide. Control experiments showed that iodine could greatly suppress the self-coupling of cyanoalkyl radicals, thus making the sulfuration proceed smoothly.
Related Papers
- → Sulfurization of γ-oxo esters; study of the resulting sulfur compounds(1977)19 cited
- → Studies on Novel Synthetic Methodologies. Part 29. Efficient, Selective Deprotection of Aromatic Acetates Catalyzed by Amberlyst‐15 or Iodine.(2003)
- → ChemInform Abstract: Novel Synthesis of Selenones: Application to the Synthesis of Alkyl Cyclopropanecarboxylates.(1988)
- → ChemInform Abstract: DIORGANOSTANNYLENES. II. PHOTOLYTIC REACTION OF DIPHENYLTIN WITH ALKYL HALIDES(1977)
- → ChemInform Abstract: Iodine‐Promoted Radical Cyclization in Water: A Selective Reaction of 1,6‐Enynes with Sulfonyl Hydrazides.(2016)