Rh-Catalyzed Annulations of N‑Methoxybenzamides and Ketenimines: Sterically and Electronically Controlled Synthesis of Isoquinolinones and Isoindolinones
Rh-Catalyzed Annulations of N‑Methoxybenzamides and Ketenimines: Sterically and Electronically Controlled Synthesis of Isoquinolinones and Isoindolinones
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Rh 催化的 N-甲氧基苯甲酰胺和烯酮亚胺的环化：异喹啉酮和异吲哚啉酮的空间和电子控制合成
DOI：
10.1021/acs.joc.7b00258
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Yanguang Wang
中科院分区：
文献类型：
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作者：
Xiaorong Zhou;Zhiyin Zhang;Hongyang Zhao;Ping Lu;Yanguang Wang
报道了铑催化烯酮亚胺与 N-甲氧基苯甲酰胺的 C-H 活化/成环反应。反应的结果取决于烯酮亚胺的结构。 β-烷基取代的烯酮亚胺以正式的[4+2]成环方式提供3-亚氨基异喹啉-1(2H)-酮，而β-酯取代的烯酮亚胺以正式的[4+1]成环方式提供3-氨基异吲哚啉-1-酮。合成的[4 + 2]产物经过分子内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，可以通过一锅法Rh催化成环/Cu催化C-N偶联序列直接由烯酮亚胺和N-甲氧基苯甲酰胺制备。
Rhodium-catalyzed C–H activation/annulation reactions of ketenimines withN-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 andN-methoxybenzamides by a one-pot Rh-catalyzed annulation/Cu-catalyzed C–N coupling sequence.