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One-pot hydrogen peroxide and hydrohalic acid induced ring closure and selective aromatic halogenation to give new ring-fused benzimidazoles

Gurry, Michael
; 
Sweeney, Martin
; 
McArdle, Patrick
; 
Aldabbagh, Fawaz
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Publication Date
2015-05-19
Keywords
Chemistry, Free chlorine, Derivatives, Reactivity, TBHP
Type
Article
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Citation
Michael Gurry, Martin Sweeney, Patrick McArdle, Fawaz Aldabbagh (2015) 'One-Pot Hydrogen Peroxide and Hydrohalic Acid Induced Ring Closure and Selective Aromatic Halogenation To Give New Ring-Fused Benzimidazoles'. Organic Letters, 17 :2856-2859.
Abstract
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.
Funder
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Publisher
American Chemical Society
Publisher DOI
10.1021/acs.orglett.5b01317
Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Collections
School of Biological and Chemical Sciences (Scholarly Articles)