Organopromoted direct synthesis of 6-iodo-3-methylthioimidazo[1,2-a]pyridines via convergent integration of three self-sorting domino sequences?

Organic & Biomolecular Chemistry Pub Date: 2015-07-17 DOI: 10.1039/C5OB01313E

Abstract

An NH2CN-promoted convergent integration of three self-sorting domino sequences is described for the construction of 6-iodo-3-methylthioimidazo[1,2-a]pyridines from aryl methyl ketones and 2-aminopyridines. This strategy allows the construction of an imidazo[1,2-a]pyridine ring along with methylthiolation at C-3 and iodination at C-6. Preliminary mechanistic studies indicate that this process terminates at the iodination stage without Kornblum oxidation in the presence of I2 and DMSO.

Graphical abstract: Organopromoted direct synthesis of 6-iodo-3-methylthioimidazo[1,2-a]pyridines via convergent integration of three self-sorting domino sequences
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