Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles in a sustainable solvent

A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocycles (55 examples, up to 95% yield, including modification of pharmaceuticals and natural products) such as thioflavones, benzimidazo[2,1- a ]isoquinolin-6(5 H )-ones, ind...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 24; no. 4; pp. 1732 - 1737
Main Authors Zeng, Fan-Lin, Xie, Kun-Chen, Liu, Yu-Ting, Wang, He, Yin, Peng-Cheng, Qu, Ling-Bo, Chen, Xiao-Lan, Yu, Bing
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.02.2022
Royal Society of Chemistry
Subjects
Acylation
air
Air temperature
ambient temperature
carbonates
Catalysts
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
drugs
Green & Sustainable Science & Technology
Green chemistry
heterocyclic compounds
Light effects
Natural products
Organic solvents
Oxidants
Oxidizing agents
Physical Sciences
Reagents
Room temperature
Science & Technology
Science & Technology - Other Topics
Solvents
ROUTE
ORGANIC TRANSFORMATIONS
ACYLATION
ALKYLATION
ACYL RADICALS
PHOTOCATALYSIS
METAL
QUINOXALIN-2(1H)-ONES
INDOLES
CARBOXYLIC-ACIDS
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Summary:A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocycles (55 examples, up to 95% yield, including modification of pharmaceuticals and natural products) such as thioflavones, benzimidazo[2,1- a ]isoquinolin-6(5 H )-ones, indolo[2,1- a ]isoquinolin-6(5 H )ones, quaternary 3,3-dialkyl 2-oxindoles, quinoxalin-2(1 H )-ones, and benzo[ e ][1,2,3]oxathiazine 2,2-dioxides in a green solvent (dimethyl carbonate) under air and room temperature conditions. This practical acylation process was achieved using 4-acyl-1,4-dihydropyridines (acyl-DHPs) as acylating reagents under mild conditions, avoiding the use of catalysts, bases, additional oxidants, and traditional organic solvents. A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocyclesunder air and room temperature conditions.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/d1gc04218a
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SourceType-Scholarly Journals-1
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ISSN:1463-9262
1463-9270
1463-9270
DOI:10.1039/d1gc04218a