94255-69-3Relevant articles and documents
Preparation of phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin
Yanai, Kei,Togo, Hideo
, (2020/10/07)
Treatment of N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin in 1,2-dichloroethane under irradiation with a tungsten lamp, followed by the reaction with tBuOK gave the corresponding 6-arylphenanthridines and 6-unsubstituted phenanthridines in good to moderate yields, respectively. The reaction proceeds through an oxidative cyclization onto the aromatic ring by sulfonamidyl radicals formed from the N-iodosulfonamides. The present reaction is a one-pot method for the preparation of both 6-arylphenanthridines and 6-unsubstituted phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides under transition-metal-free conditions.
6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine
Kobayashi, Eiji,Kishi, Atsushi,Togo, Hideo
, p. 7335 - 7347 (2019/11/22)
Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.
Preparation of Phenanthridines from o-Cyanobiaryls via Addition of Organic Lithiums to Nitriles and Imino Radical Cyclization with Iodine
Kishi, Atsushi,Moriyama, Katsuhiko,Togo, Hideo
, p. 11080 - 11088 (2018/09/12)
Simple treatment of 2-cyanobiaryls with methyllithium, ethylmagnesium bromide, butyllithium, phenyllithium, p-methylphenyllithium, etc., followed by the reaction with water and then with molecular iodine at 60 °C provided efficiently 6-methyl-, 6-ethyl-, 6-butyl-, 6-phenyl, 6-(p-methylphenyl)phenanthridines, etc., in good yields, respectively. Here, imines formed through the addition of carbanion onto the nitriles reacted with molecular iodine to form N-iodoimines smoothly, and their warming treatment induced the formation of imino radicals that smoothly cyclized onto the aryl group to give 6-alkyl- and 6-arylphenanthridines.