1372608-86-0Relevant academic research and scientific papers
Photochemical arylation of Bronsted acids with 2-azidobenzimidazole
Sudakow, Alex,Jones, Peter G.,Lindel, Thomas
, p. 681 - 684 (2012/03/11)
Irradiation of N-benzylated 2-azidobenzimidazoles at 300 nm in the presence of an excess amount of carboxylic acids results in a novel regioselective synthesis of 2-amino-6-oxybenzimidazoles in isolated yields of 60-70 %. It is also possible to regioselectively introduce 6-bromo, 6-chloro, and 6-triflyloxy groups. Irradiation in dichloromethane in the absence of external nucleophiles revealed that after loss of nitrogen, the benzimidazolylnitrene probably undergoes coarctate ring opening to an N-cyano diaza-o-xylylene intermediate. Photolysis of 2-azidobenzimidazoles in the presence of carboxylic or sulfonic acidsleads to regioselective oxygenation of the 6-position in good yield. Copyright
