A Scaffold‐Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides

A “branching–folding” synthetic strategy that affords a range of diverse cyclic benzo‐sulfonamide scaffolds is presented. Whereas different annulation reactions on common ketimine substrates build the branching phase of the scaffold synthesis, a common hydrogenative ring‐expansion method, facilitated by an increase of the ring‐strain during the branching phase, led to sulfonamides bearing medium‐sized rings in a folding pathway. Cell painting assay was successfully employed to identify tubulin targeting sulfonamides as novel mitotic inhibitors.