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One-Pot Hydrogen Peroxide and Hydrohalic Acid Induced Ring Closure and Selective Aromatic Halogenation To Give New Ring-Fused Benzimidazoles

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posted on 2015-06-05, 00:00 authored by Michael Gurry, Martin Sweeney, Patrick McArdle, Fawaz Aldabbagh
A new series of selectively dichlorinated and dibrominated five- to eight-membered-ring [1,2-a]-fused benzimidazoles and [1,4]­oxazino­[4,3-a]­benzimidazoles are synthesized in mostly high yields of >80% using the reaction of hydrogen peroxide and hydrohalic acid with commercially available o-cyclic amine substituted anilines. Domestic bleach with HCl can also be used for a one-pot ring closure and chlorination.