Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
J Org Chem. 2017 Apr 7;82(7):3787-3797. doi: 10.1021/acs.joc.7b00258. Epub 2017 Mar 30.
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.
报道了铑催化的偕亚胺与 N-甲氧基苯甲酰胺的 C-H 活化/环化反应。反应的结果取决于偕亚胺的结构。β-烷基取代的偕亚胺以[4+2]环化方式提供 3-亚氨基异喹啉-1(2H)-酮，而β-酯取代的偕亚胺以[4+1]环化方式提供 3-氨基异吲哚啉-1-酮。合成的[4+2]产物经历分子内 Cu 催化的 C-N 偶联，转化为苯并[4,5]咪唑并[1,2-b]异喹啉-11-酮，该产物可以通过一锅法 Rh 催化的环化/Cu 催化的 C-N 偶联序列由偕亚胺和 N-甲氧基苯甲酰胺直接制备。
