Scalable Diastereoselective Electrosynthesis of Spiro[benzofuran-2,2′-furan]-3-ones DOI
Issa Yavari, Sina Shaabanzadeh,

Kiyana Ghafouri

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 425 - 432

Published: Dec. 12, 2023

Spirobenzofuran scaffolds, because of their three-dimensional structure, are incorporated into several valuable natural products and drug candidate molecules. Herein, with the assistance electrosynthesis, we introduce a novel electrochemical approach for achieving spirobenzofurans in user-friendly operationally simple undivided cell setup under constant current. This metal-catalyst-free procedure afforded spiro[benzofuran-2,2′-furan]-3-ones high diastereoselectivity. Compatibility gram-scale synthesis along convenient accessibility reaction instruments starting materials collectively raised importance this protocol compared to previous challenging methods. Furthermore, mechanistic cognizance is obtained by investigation cyclic voltammetry spectra reactants.

Language: Английский

Visible-light-mediated oxidant-free tandem acylmethylation/ipso-spirocyclization of N-arylpropiolamides: Access to 3-acylmethyl azaspiro[4,5]trienones DOI

Binfeng Zhu,

Guokai Li, Mingzhu Li

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 582, P. 115120 - 115120

Published: May 2, 2025

Language: Английский

Citations

0

Electrochemical Synthesis of Sulfonamide Derivatives: Electrosynthesis Conditions and Reaction Pathways DOI Creative Commons
Mohammad Reza Talebi, Davood Nematollahi

ChemElectroChem, Journal Year: 2024, Volume and Issue: 11(10)

Published: Feb. 15, 2024

Abstract In 2014, the World Health Organization called drug resistance to antibiotics a “major global threat”. Therefore, ever‐increasing human need for new with greater effectiveness and fewer side effects is necessity. Meanwhile, sulfonamides are among most widely used in world. this review, attention has been paid key points raised various papers field of electrosynthesis these compounds, considering their positive negative aspects, including interaction as much possible principles green chemistry absence environmental risks, low cost versatility scalability method along acceptable efficiency. following, we will discuss research focused on synthesis sulfonamide derivatives based oxidation or reduction compounds which take place working electrode surface.

Language: Английский

Citations

3

Single Step Upgradation of Isatin to Bioactive Fused Heterocycles via Ring Expansion Reactions DOI

Raksha Chandramani,

Ajil R. Nair, Anjana Sreekumar

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(4)

Published: Dec. 6, 2023

Abstract Isatin, also known as indoline‐2,3‐dione, is a fused, N ‐heterocyclic aromatic compound first isolated and purified in 1841. Since then, isatin its derivatives emerged hot research topic for the scientific community. The number of publications on justifies their popularity. Researchers explored isatins potential candidates multidisciplinary areas, including medicinal chemistry, synthetic organic polymer science. Synthetic chemists’ perspective tailoring family members led to more efficient synthesis strategies which ring‐opening reactions were particularly significant due product's importance. Our investigation aims group different types cascade ring expansion synthesise fused heterocyclic compounds such quinolines, quinazolinones, acridines, acridones, few spiro compounds, all highlight an inevitable role field chemistry.

Language: Английский

Citations

7

Organocatalytic Asymmetric Tandem Reaction of Indene-Based Dienes for the Synthesis of Enantioenriched Spirodihydrofluorenes and Fluorenylamine-ketoximes Containing Axial Elements DOI
Wenli Xu, Yuhan Zhang,

J.‐Q. Yuan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

Language: Английский

Citations

1

Advances in the Synthesis of Azaspiro[4.5]trienones DOI Open Access
Jing Tang, Wenkun Luo, Jun Zhou

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(9), P. 3006 - 3006

Published: Jan. 1, 2023

As one of the most important structural motifs in natural compounds and active pharmaceutical ingredients, azaspiro[4.5]trienonesderivatives have been widely used field organic synthesis due to their excellent properties biological activities.In recent years, several methods, such as transition metal involvement, visible light promotion, metal-free involvement electrochemical efficiently construct various functional groups azaspiro[4.5]trienones.The advances azaspiro[4.5]trienones are reviewed, representative substrates reaction mechanisms summarized discussed.

Language: Английский

Citations

3

Base-Mediated Chemodivergent [4 + 1] and [2 + 1] Cycloadditions of N-Alkylpyridiniums and Enones DOI

Dehao Duan,

Yifei Wei,

Tianyou Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 11959 - 11974

Published: Aug. 27, 2024

Divergent synthesis of structurally different products from the same kinds starting materials is highly synthetically useful but very challenging. Herein, we reported a base-mediated chemodivergent [4 + 1] and [2 cycloaddition N-alkylpyridinium enone under mild conditions, leading to furan-fused bicycles with high diastereoselectivity spirobicycles, respectively, moderate yields. N-Alkylpyridinium salts were modular nucleophilic transfer reagents C1 synthons, which underwent tandem Michael addition α,β-unsaturated ketones cyclization base conditions. Late-stage derivatization 4-propyldicyclohexylanone an important industrial raw liquid crystal display (LCD) screens was realized. In vitro, compound 3f exhibited good activities against human colon cancer cells (HCT116) IC50 values in 9.82 ± 0.27 μM. Further biological evaluations investigated mechanism effective inhibition cell growth, including apoptosis ratio detection, cycle analysis, migration capacity HCT116 cells. effect studies, complex increased percentage apoptotic 26.8% (15 μM).

Language: Английский

Citations

0

Design of Synthetic Strategies towards Sulfur Containing Scaffolds DOI
Sambasivarao Kotha, Priti Khedkar

Synthesis, Journal Year: 2024, Volume and Issue: 57(02), P. 275 - 295

Published: Aug. 28, 2024

Abstract The utilization of sulfur heterocycles in organic synthesis has attracted significant attention due to their wide-ranging applications. This review showcases the syntheses diverse embedded with amino acid derivatives, polycycles, spirocycles, cyclophanes, and other complex scaffolds. reported methods extend beyond compound highlight use different reagents for constructing heterocycles. Review also discusses utility a variety sulfur-containing starting materials generation target molecules. 1 Introduction 2 Potassium Thioacetate 3 Thiazolidine-2,4-dione 4 Rhodanines 5 Sodium Sulfide 6 Thiotetronic Acid 7 Thiadiazoles 8 Thiophene 9 Rongalite 10 Sulfur Dioxide 11 Divinyl Sulfone 12 Heterocycles Based on Boronic Acids 13 Miscellaneous 14 Summary

Language: Английский

Citations

0

Modern electrosynthesis of spiro compounds DOI
Michaïl N. Elinson,

Yu. E. Ryzhkova,

Fedor V. Ryzhkov

et al.

Russian Chemical Bulletin, Journal Year: 2024, Volume and Issue: 73(7), P. 1845 - 1865

Published: July 1, 2024

Language: Английский

Citations

0

Electrochemical Selenized Reaction of N-Arylbicyclo[1.1.0]butane-1-carboxamides: Access to 3-(Arylselanyl)spiro[cyclobutane-1,3′-indolin]-2′-one Derivatives DOI

Jiyao Liu,

Yuliang Qian,

Hongrong Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15914 - 15923

Published: Oct. 23, 2024

A novel selenized reaction of N-arylbicyclo [1.1.0]butane-1-carboxamides with diselenide for the synthesis polycyclic indoline derivatives is developed under electrochemical conditions. The achieved by bicyclo[1.1.0]butane strain-release and intramolecular cyclization process. In addition, this approach features a wide range substrates, good group tolerance, shorter time, mild

Language: Английский

Citations

0

Electrochemical Organic Synthesis DOI
Hai‐Chao Xu

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2797 - 2798

Published: Aug. 29, 2023

Received: 03 August 2023 Accepted after revision: Article published online:29

Language: Английский

Citations

1