Rh-Catalyzed Annulations of N-Methoxybenzamides and Ketenimines: Sterically and Electronically Controlled Synthesis of Isoquinolinones and Isoindolinones.
Rhodium-catalyzed C-H activation/annulation reactions of ketenimines with N-methoxybenzamides are reported. The outcome of reactions is dependent on the structure of ketenimines. The β-alkyl-substituted ketenimines furnish 3-iminoisoquinolin-1(2H)-ones in a formal [4 + 2] annulation manner, while the β-ester substituted ketenimines afford 3-aminoisoindolin-1-ones in a formal [4 + 1] annulation manner. The synthesized [4 + 2] products undergo an intramolecular Cu-catalyzed C-N coupling to be converted to benzo[4,5]imidazo[1,2-b]isoquinolin-11-ones, which can be directly prepared from ketenimines and N-methoxybenzamides by a one-pot Rh-catalyzed annulation/Cu-catalyzed C-N coupling sequence.
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Xiaorong
X
Zhou
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Zhiyin
Z
Zhang
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Hongyang
H
Zhao
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Ping
P
Lu
Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Yanguang
0000-0002-5096-7450
Y
Wang