Ruthenium(II)-catalyzed synthesis of indazolone-fused cinnolines via C-H coupling with diazo compounds

被引：36
|
作者：
Su, Lin [1 ,2 ]
Yu, Zheng [3 ]
Ren, Peiling [3 ]
Luo, Zhi [4 ]
Hou, Wei [1 ,2 ]
Xu, Hongtao [3 ]
机构：
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, IDD & CB, Hangzhou 310014, Zhejiang, Peoples R China
[3] ShanghaiTech Univ, Shanghai Inst Adv Immunochem Studies, Shanghai 201210, Peoples R China
[4] Shanghai Evergene Biotech Co Ltd, Shanghai 201203, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 39期
基金：
中国博士后科学基金;
关键词：
CATALYZED INTRAMOLECULAR CYCLIZATION; N BOND FORMATION; CARBENOID FUNCTIONALIZATION; RHODIUM(III)-CATALYZED SYNTHESIS; RH(III)-CATALYZED ANNULATION; ALPHA-DIAZOACETAMIDES; DIRECT ACCESS; PI-SYSTEMS; ACTIVATION; INDOLES;
D O I：
10.1039/c8ob02071j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A robust, efficient and scalable method for the synthesis of 12H-indazolo[2,1-a]cinnolin-12-ones was developed. Significantly, a less developed cationic complex [Ru(p-cymene)(MeCN)(3)(SbF6)(2)] was found to be effective for this transformation. In this reaction, a tandem pathway of C-H ruthenation, Ru(ii)-carbene formation, migratory insertion and condensation was involved. The results of a primary mechanistic study suggested that the C-H activation process might follow an electrophilic-type metalation/deprotonation mechanism.
引用
收藏
页码：7236 / 7244
页数：9
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