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Updated: Aug 2, 2025

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Iodine(III)-Mediated Oxidation of Anilines to Construct Dibenzazepines
Carmen Margaret White1, Naranchimeg Zorigt1, Tianning Deng1
1Department of Chemistry, University of Illinois Chicago, 845 W Taylor St. MC 111, Chicago, IL, 60607, USA.
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.
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