Regiodivergent Functionalization of Isoquinoline-1,3(2H,4H)-dione Derivatives via Aerobic Umpolung

被引：4

作者：

Li, Ying-Xian ^{[1
]}

Feng, Xiao-Bing ^{[2
]}

Jia, Xue-Min ^{[1
]}

Jin, Huang ^{[1
]}

Chen, Fei ^{[1
]}

Zhao, Yong-Long ^{[1
]}

Zhang, Ji-Quan ^{[1
]}

Wang, Jian-Ta ^{[1
]}

Guo, Bing ^{[3
]}

Tang, Lei ^{[1
]}

Yang, Yuan-Yong ^{[1
]}

机构：

[1] Guizhou Med Univ, Sch Pharm, State Key Lab Funct & Applicat Med Plants, Guizhou Prov Engn Technol Res Ctr Chem Drug R&D, Guiyang 550014, Peoples R China

[2] Peoples Hosp Luzhou, Dept Orthopaed, Luzhou 646000, Peoples R China

[3] Guizhou Med Univ, Guizhou Prov Key Lab Pathogenesis & Drug Res Comm, Guiyang 550004, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 10卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Aerobic oxidation; Isoquinoline-1; 3(2H; 4H)-dione; Organo-catalysis; Aldol addition; Difunctionalization; ENANTIOSELECTIVE ALPHA-HYDROXYLATION; H BOND FUNCTIONALIZATION; CARBON-CARBON BOND; SELECTIVE INHIBITORS; AIR-OXIDATION; DESIGN; OXINDOLES; KETONES; POTENT; OXYGEN;

D O I：

10.1002/ajoc.202100194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and green methodology for the regiodivergent functionalization of isoquinoline-1,3(2H,4H)-diones under aerobic conditions was developed. Under a catalytic amount of base, heteroatom nucleophiles went through an imide opening/ring contraction sequence to give the thermodynamic controlled product; while carbon based nucleophiles led to kinetic controlled aldol type product. Moreover, the aldol type product was transformed into the benzo[c]phenanthridine core structures under transition metal free condition, which provides an environmental benign access to this framework.

引用

页码：1508 / 1513

页数：6

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