1.
J Org Chem
; 79(23): 11395-408, 2014 Dec 05.
Article
in English
| MEDLINE
| ID: mdl-25369362
ABSTRACT
The hypervalent iodine(III) reagent-induced the direct intramolecular C-N cyclization of N-(biphenyl)pyridin-2-amines to 6-arylbenzimidazoles and N-pyridinyl-9H-carbazoles is presented. The substituent electronic effects governing the formation of benzimidazoles and carbazoles from the reaction of N-(biphenyl)pyridin-2-amines with hypervalent iodine(III) reagents is investigated. Radical trapping and UV-vis spectroscopic experiments on the detection of the cation radical are carried out. Rational mechanisms for these reactions are presented. The selective intramolecular C-N and C-O cyclization of N-(biphenyl)acetamides based on the substituent electronic effects is also presented.