Visible-Light-Driven Metal-Free C-H Functionalization: Access to New Bioactive Tetrahydroisoquinoline-Butenolide Hybrids via Domino Amine Oxidation/Vinylogous Mannich Reaction

被引：0

作者：

Kersting, Lena ^{[1
,2
]}

Kuhn, Leah ^{[3
]}

Anokhin, Maksim ^{[1
,2
]}

Schuster, Florian ^{[1
,2
]}

Haeberli, Cecile ^{[4
,5
]}

Sambyal, Shainy ^{[6
]}

Kumar, Halmuthur M. Sampath ^{[6
]}

Keiser, Jennifer ^{[4
,5
]}

Alabugin, Igor ^{[3
]}

Tsogoeva, Svetlana B. ^{[1
,2
]}

机构：

[1] Friedrich Alexander Univ Erlangen Nurnberg, Organ Chem 1, Dept Chem & Pharm, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany

[2] Friedrich Alexander Univ Erlangen Nurnberg, Interdisciplinary Ctr Mol Mat ICMM, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany

[3] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

[4] Swiss Trop & Publ Hlth Inst, Kreuzstr 2, CH-4123 Allschwil, Switzerland

[5] Univ Basel, Peterspl 1, CH-4001 Basel, Switzerland

[6] CSIR Indian Inst Chem Technol, Organ Synth & Proc Chem Div, Hyderabad 500007, India

来源：

CHEMPHOTOCHEM | 2022年 / 6卷 / 08期

基金：

美国国家科学基金会;

关键词：

Domino reaction; visible light; metal-free C-H functionalization; tetrahydroisoquinoline-butenolide hybrids; antischistosomal and anti-cancer activities; DFT calculations; OXYGEN; THIOUREA; PHOTOCATALYSIS; PHOTOOXIDATION; FLUORESCEIN; DERIVATIVES; CATALYSIS; DESIGN;

D O I：

10.1002/cptc.202200109

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient metal-free visible-light-driven two-step domino reaction towards new bioactive tetrahydroisoquinoline-butenolide hybrid compounds was developed for the first time. The combination of fluorescein as photosensitizer and thiourea as an additive was found to be the most effective way to promote an aerobic amine oxidation/vinylogous Mannich domino reaction sequence with yields up to 97% for a broad substrate scope. Both experimental and computational evidence supported the crucial role of singlet oxygen in the developed C H functionalization reaction. Furthermore, the data suggest that thiourea is essential due to its ability to act as an electron-transfer mediator and/or scavenger of reactive oxygen species. In addition, in vitro studies of tetrahydroisoquinoline-butenolide hybrid compounds demonstrated their high antischistosomal and anti-cancer activities.

引用

页数：10

共 3 条

[1] Progress of Metal-Free Visible-Light-Driven α-C-H Functionalization of Tertiary Amines: A Decade Journey
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ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (05)
[2] Metal- and photocatalyst-free visible-light-promoted regioselective selenylation of coumarin derivatives via oxidation-induced C-H functionalization
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ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20): : 2974 - 2979
[3] Base- and metal-free visible-light driven site-selective α-C(sp3)-H functionalization reaction of glycine derivatives with hydroxamic acid derivatives
He, Shiyun
Fan, Hongying
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ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (11) : 3119 - 3123

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