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.
In the title molecule, C24H28N6O2S2, the dihedral angle between the aromatic ring planes is 42.2 (1)°. In the crystal structure, the hydroxy groups are involved in O—H⋯S hydrogen bonding, which links the molecules into corrugated layers propagating parallel to the bc plane.
The molecule of the title compound, C11H19N5O4, contains three fused rings, namely two nearly planar imidazole rings and one non‐planar triazine ring. The latter ring displays a chair conformation. Two hydroxylmethylene groups are linked to two N atoms from separate rings of the glycoluril system.
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