This poster presents the discovery and optimization of two cascade sequences that enable the formation of unique pharmacologically relevant scaffolds in a mere two steps. Initial diversity is installed via an Ugi reaction with concomitant acid treatment and heating triggering a cascade reaction. The cascades proceed through 1,5-benzodiazepines which subsequently undergo an acid or heat promoted (<i>Z</i>)-stereo-selective ring contraction to afford families of highly substituted benzimidazol-2-ones. This expeditious, operationally friendly methodology allows access to both skeletal diversity and individual scaffold congeners. The scope of these reaction sequences, mechanism, and X-ray crystallography studies will be discussed.

Benzimidazol-2-one scaffolds derived from unique domino processes centered upon elegant benzodiazepine ring rearrangements

249th National Meeting (2015)

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