Tunable multicomponent reactions that allow access to diverse biologically appealing nitrogen-enriched heterocycles are described. Employing 2-hydrazino-azines, aldehyde or ketone and an isonitrile in a [5+1] cycloaddition reaction leads to unique bicyclic pyridotriazine scaffolds. Switching the isocyanide for a variety of reacting inputs (isocyanates, isothiocyanates, cyclic anhydrides and acyl chlorides) generates triazolopyridines in a single step. Additionally, a one-pot protocol using activated phenyl hydrazines, aldehydes and isocyanates renders dihydroindazole-carboxamides nucleus. The operational simplicity associated with these procedures for plate based mass production and the potential biological relevance of the resulting chemotypes suggest they will earn high interest from the medicinal chemistry community.

Diversity-enabling multicomponent reactions of 2-hydrazino-azines for the synthesis of nitrogen-enriched bicyclic heterocycles

248th National Meeting (2014)

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