Facile solid-phase synthesis of 2,3-disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones

Add time:07/15/2019    Source:sciencedirect.com

We report herein the facile solid-phase synthesis of 2,3-disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones using 7-fluoro-4-methyl-6-nitro-2-oxo-2H-1-benzopyran-3-carboxylic acid as the scaffold. The fluorine of the resin-bound scaffold was first replaced by a primary amine. Reduction of the nitro group with tin(II) chloride afforded an o-dianilino intermediate that was treated with an aldehyde followed by the addition of 2,3-dichloro-5,6-dicyanoquinone (DDQ). 2,3-Disubstituted 6H-pyrano[2,3-f]benzimidazole-6-ones were obtained in high purity and good yield after cleavage.

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