4.4 Article

Metal-Free Mediated C-3 Methylsulfanylation of Imidazo[1,2-a]-pyridines with Dimethyl Sulfoxide as a Methylsulfanylating Agent

Journal

SYNLETT
Volume 28, Issue 14, Pages 1795-1800

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588419

Keywords

methylsulfanylation; C-S bond formation; imidazopyridines; dimethyl sulfoxide; iodine

Funding

  1. National Nature Science Foundation of China [21602202]
  2. Science Foundation of Zhejiang Sci-Tech University [15062092-Y, 1206820-Y, 1206821-Y]
  3. Zhejiang Provincial Top Key Academic Discipline of Chemical Engineering and Technology of Zhejiang Sci-Tech University

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A simple approach is described for the regioselective C-3 methylsulfanylation of imidazo[1,2-a] pyridines through diiodine-mediated, acetone-promoted, C-S bond construction with dimethyl sulfoxide as both the source of the methylsulfanyl moiety and the solvent. Preliminary mechanistic investigations indicated that three different reaction mechanisms might be involved in the transformation.

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