Recent Advances in The Electrochemical Functionalization of N-heterocycles DOI
Manoj Kumar Yadav, Sushobhan Chowdhury

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The review aims to provide a clear picture of the possible electron transfer pathways, electrochemical behavior different N-heterocycles, and functionalization reagents achieve desired functionalization/modification N-heterocycles.

Language: Английский

Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α-Aminomethylation of Quinoxalin-2(1H)-ones via Electron Donor–Acceptor Complexes DOI
Devidas A. More, Sachin R. Shirsath,

M. Muthukrishnan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13339 - 13350

Published: Aug. 31, 2023

We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation photoactivated electron donor–acceptor complex between present method provides mild environmentally friendly protocol that exhibits good atom economy excellent functional group tolerance to obtain library biologically significant α-aminomethylated in yields.

Language: Английский

Citations

12
Electrochemical Decarboxylative Addition of N‐Aryl Glycines to Enaminones: Access to C3‐Aminomethyl Chromones DOI

Siyang Han,

Chengcheng Fang,

Yaoge Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(28)

Published: May 1, 2024

Abstract An electrochemical decarboxylative addition of N ‐substituted glycines to enaminones has been developed and conducted under oxidant‐, catalyst‐, light‐free conditions in acetonitrile at room temperature by using electron as the traceless oxidant, which provided a green approach access C3‐aminomethyl chromones. The resulting products were formed through radical addition/oxidation/cyclization or electrophilic addition/cyclization pathway could act valuable building blocks construct polysubstituted pyrimidine derivatives.

Language: Английский

Citations

4
Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction DOI
S. M. Wahidur Rahaman,

Suhag Singh Sahay,

Annu Kumari

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10773 - 10784

Published: July 17, 2024

This study showcases successfully switchable approaches to accomplish the C3-aryl methylation and C3- amino of privileged nitrogen-containing pharmaceutical compounds "imidazopyridines" with distinct amines, which surmounts long-standing requirement for a superfluous directing group. These two transformations manifest pronounced regio- chemo-divergent behavior, demonstrating unprecedented multicomponent "abnormal Mannich Mannich-type" reactions. The remarkable environmentally benign protocol has been efficiently extended concise synthesis late-stage derivatization.

Language: Английский

Citations

3
C3-Alkylation of Imidazo[1,2-a]pyridines via Three-Component Aza-Friedel–Crafts Reaction Catalyzed by Y(OTf)3 DOI Creative Commons
Kai Yang,

Cai-Bo Chen,

Zhaowen Liu

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3463 - 3463

Published: July 24, 2024

As an important class of nitrogen-containing fused heterocyclic compounds, imidazo[1,2-a]pyridines often exhibit significant biological activities, such as analgesic, anticancer, antiosteoporosis, anxiolytic, etc. Using Y(OTf)

Language: Английский

Citations

2
Recent advances in phosphorylation of hetero-nucleophilic reagents via P–H bond cleavage DOI
Sifeng Li, Lijing Fang, Qian Dou

et al.

Tetrahedron, Journal Year: 2023, Volume and Issue: 136, P. 133344 - 133344

Published: March 6, 2023

Language: Английский

Citations

5
Electrosynthesis of Highly Functionalized Polycyclic N-Heteroaromatics through Cascade Radical Cyclization and Alkoxylation in Batch and Continuous-Flow DOI
Jiawei Chen,

Yaqi Qiao,

Wenjing Guan

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2023, Volume and Issue: 11(50), P. 17728 - 17738

Published: Dec. 6, 2023

Electrochemical radical cascade cyclization has been recognized as a powerful, straightforward, and environmentally-friendly synthetic tool to give highly functionalized polycyclic aromatic compounds but remains challenging difficult because of the instability intermediates under electrolysis conditions, especially using user-friendly undivided cell. Herein, we report novel electrosynthesis pyridine-fused N-heteroaromatics through dehydrogenative alkoxylation oxidant-free conditions. This electrochemical synthesis methodology features green mild reaction good functional group tolerance, use readily available substrates. Moreover, attributed flow cells, steady production large-scale preparation can be conveniently achieved only small amounts electrolytes.

Language: Английский

Citations

4
Recent Advances in the Electrochemical Functionalization of Imidazoheterocycles DOI
Sifeng Li

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract Imidazoheterocycles have extensive applications in the pharmaceutical industry and agrochemicals. A comprehensive overview has been provided on current advancements electrochemical functionalization of imidazo‐fused heterocycles, which classified into ten different types reactions. Electrochemical synthesis emerged as a highly effective method for producing organic molecules, especially context sustainable development. Employing electrons traceless oxidant, several C−H reactions heterocycles achieved at either C3 or C5 positions. Electrons may serve reducing agent to synthesize pyridine rings that are partially fully saturated imidazo[1,2‐ ]pyridines. The purpose review is attract interest scientific community promote additional research imidazoheterocycles using methods.

Language: Английский

Citations

1
Metal-free C-3 selective C(sp2)–C(sp3) heteroarylation of anilines with imidazo[1,2-a]pyridine derivatives via cross-dehydrogenative coupling DOI Creative Commons
Kai Wang,

Xiaoxue Du,

Pengfei Zhang

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(31), P. 21685 - 21689

Published: Jan. 1, 2023

A metal-free and straightforward method for the construction of C-3 heteroarylation-containing imidazo[1,2- a ]pyridine has been reported, utilizing N,N -dimethylaniline as methylenation source furnishing desired products in good to excellent yields.

Language: Английский

Citations

2
Transition-metal-free synthesis of triarylmethanes via Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives DOI Creative Commons

Xinlei Fu,

Longhui Wu,

Xiaohua Guo

et al.

Journal of Saudi Chemical Society, Journal Year: 2024, Volume and Issue: 28(4), P. 101883 - 101883

Published: May 29, 2024

A facile, transition-metal-free, HFIP-promoted method for the synthesis of triarylmethanes through direct Friedel-Crafts reactions imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives has been described, which allows efficient containing in good to satisfactory yields at room temperature. This transformation features simple operation, excellent functional group tolerance, and a broad substrate scope.

Language: Английский

Citations

0
Recent Advances in The Electrochemical Functionalization of N-heterocycles DOI
Manoj Kumar Yadav, Sushobhan Chowdhury

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The review aims to provide a clear picture of the possible electron transfer pathways, electrochemical behavior different N-heterocycles, and functionalization reagents achieve desired functionalization/modification N-heterocycles.

Language: Английский

Citations

0