Issue 33, 2015

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

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

Supplementary files

Article information

Article type
Communication
Submitted
27 Jun 2015
Accepted
17 Jul 2015
First published
17 Jul 2015

Org. Biomol. Chem., 2015,13, 8807-8811

Author version available

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

S. Liu, H. Xi, J. Zhang, X. Wu, Q. Gao and A. Wu, Org. Biomol. Chem., 2015, 13, 8807 DOI: 10.1039/C5OB01313E

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