1220294-96-1Relevant articles and documents
Tuned C-H functionalization to construct aza-podophyllotoxin/aza- conidendrin derivatives by means of domino cyclization
Hu, Yimin,Qu, Yuan,Wu, Fenghua,Gui, Jinghan,Wei, Yun,Hu, Qiong,Wang, Shaowu
supporting information; scheme or table, p. 309 - 314 (2010/06/19)
An efficient domino cyclization method for the construction of aza-podophyllotoxin/aza-conidendrin derivatives has been established. Reactions of different dienes with aryl halides in the presence of a palladium catalytic system produced different kinds of podophyllotoxin derivatives through a highly regioselective C-H functionalization. Treatment of dienes with aryl halides that have electron-withdrawing substituents on the phenyl ring created aza-podophyllotoxin derivatives by means of the functionalization of the C-H bonds ortho to the C-Halide bonds of the incoming aryl halides. The reaction of dienes with 1-iodobenzene or aryl halides that incorporate electron-donating groups produced azaconidendrin derivatives by means of the functionalization of both sp3 C-H and sp2 C-H bonds. The regioselective C-H functionalization for the formation of different pseudo-podophyllotoxin/- conidendrin derivatives is proven by analyses of the 1H NMR spectra of the products and selective X-ray analyses of the structures of the products. Thus the palladium-catalyzed domino cyclization of 1,6-dienes for the preparation of aza-podophyllotoxin/aza-conidendrin derivatives can be controlled by selectively controlling the C-H functionalization.