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Radical mediated synthesis of 6‐arylphenanthridines via benzotriazole ring‐opening
Author(s) -
Katritzky Alan R.,
Yang Baozhen
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330313
Subject(s) - chemistry , benzotriazole , substituent , aryl , iodide , ring (chemistry) , copper , medicinal chemistry , photochemistry , organic chemistry , alkyl
Lithiation of diarylbenzotriazol‐1‐ylmethanes followed by addition of copper( I ) iodide gave 6‐arylphenanthridine derivatives in moderate yields. When the two aryl groups were the same or contained very different electron densities, only one product was obtained. However, when the two aryl groups exhibited electron densities of similar magnitude, two isomers were afforded. According to the substituent effect, we believe that the reactions proceed via radical intermediates formed by copper( I ) iodide.