Rh(III)- or Ru(II)-Catalyzed C-H Annulation with Vinylene Carbonate and an Unexpected Aerobic Oxidation/Deprotection Cascade to Yield Cinnolin-4(1H)-ones

被引：2

作者：

Wang, Yuqin ^{[1
]}

Zeng, Yiling ^{[1
]}

Xiao, Yi ^{[1
]}

Wang, Jinhua ^{[1
]}

Li, Shiqing ^{[1
]}

机构：

[1] Guilin Univ Technol, Coll Chem & Bioengn, Guangxi Key Lab Electrochem & Magneto Chem Funct M, Guilin 541004, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

CATALYZED OXIDATIVE ANNULATION; RHODIUM(III)-CATALYZED SYNTHESIS; CINNOLINIUM SALTS; AZOBENZENES; CYCLIZATION; ACTIVATION; EFFICIENT; FUNCTIONALIZATION; DERIVATIVES; ALKYNES;

D O I：

10.1021/acs.joc.4c01672

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition metal-catalyzed C-H annulation reactions have been extensively utilized for the synthesis of cinnolines, especially the N-protected ones; however, none of them can yield cinnolin-4(1H)-ones, a significant class of bioactive skeletons. Herein, we disclose one-pot access to cinnolin-4(1H)-ones through Rh(III)- or Ru(II)-catalyzed C-H activation/annulation of N-aryl cyclic hydrazides with vinylene carbonate, followed by an O-2/K2CO3-promoted aerobic oxidation/deprotection cascade. The pi-conjugation of the directing groups plays a crucial role in facilitating this transformation. Notably, seven-membered enolic Rh species IMC is characterized via electrospray ionization mass spectroscopy for the first time, which, along with systematic control experiments, provides compelling evidence for the mechanistic pathway encompassing alkenyl insertion, beta-oxygen elimination, protonation, and dehydration.

引用

收藏

页码：14233 / 14241

页数：9

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