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
Online AccessGet full text
ISSN1463-9262
1463-9270
1463-9270
DOI10.1039/d1gc04218a

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Abstract 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.
AbstractList 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(5H)-ones, indolo[2,1-a]isoquinolin-6(5H)ones, quaternary 3,3-dialkyl 2-oxindoles, quinoxalin-2(1H)-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 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.
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.
Author Xie, Kun-Chen
Yin, Peng-Cheng
Zeng, Fan-Lin
Chen, Xiao-Lan
Wang, He
Liu, Yu-Ting
Qu, Ling-Bo
Yu, Bing
AuthorAffiliation College of Chemistry
Green Catalysis Center
Zhengzhou University
AuthorAffiliation_xml – name: Zhengzhou University
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  givenname: Yu-Ting
  surname: Liu
  fullname: Liu, Yu-Ting
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  givenname: He
  surname: Wang
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  givenname: Peng-Cheng
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  givenname: Ling-Bo
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  fullname: Qu, Ling-Bo
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  fullname: Yu, Bing
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Issue 4
Keywords ROUTE
ORGANIC TRANSFORMATIONS
ACYLATION
ALKYLATION
ACYL RADICALS
PHOTOCATALYSIS
METAL
QUINOXALIN-2(1H)-ONES
INDOLES
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Royal Society of Chemistry
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Snippet A general visible-light-induced catalyst-/additive-free strategy was developed for the construction of various aroylated heterocycles (55 examples, up to 95%...
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SubjectTerms 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
Title Visible-light-promoted catalyst-/additive-free synthesis of aroylated heterocycles in a sustainable solvent
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