Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines.

ABSTRACT: The development of an efficient process that produces bioactive medium-sized N-heterocyclic scaffolds from 2-substituted anilines using either iodosobenzene or (bis(trifluoroacetoxy)iodo)-benzene is reported. The tether between the sulfonamide and the aryl group can be varied to access dihydroacridine-, dibenzazepine-, or dibenzazocine scaffolds. While substitution on the aniline portion is limited to electron-neutral- or electron-poor groups, a broader range of functional groups are tolerated on the ortho-aryl substituent and site selective C-NAr bond formation can be achieved. Preliminary mechanistic investigations suggest that medium-ring formation occurs via radical reactive intermediates.

SUBMITTER: White CM 

PROVIDER: S-EPMC10330268 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature