AI Article Synopsis
- The study explores how hypervalent iodine(III) reagents facilitate the direct C-N cyclization of N-(biphenyl)pyridin-2-amines into two types of compounds: 6-arylbenzimidazoles and N-pyridinyl-9H-carbazoles.
- It examines the influence of electronic effects from different substituents on the formation of these compounds during the reaction.
- Experimental methods, including radical trapping and UV-vis spectroscopy, are used to investigate reaction mechanisms and the selective cyclization of N-(biphenyl)acetamides based on electronic effects.
Article 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.
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| http://dx.doi.org/10.1021/jo501822m | DOI Listing |
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