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

Overview

Journal Chemistry

Specialty Chemistry

Date 2023 Apr 13

PMID 37053500

Authors

Carmen Margaret White

Naranchimeg Zorigt

Tianning Deng

Tom G Driver

Affiliations

Soon will be listed here.

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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