Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

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Electrochemical Enaminone-Thioamide Annulation and Thioamide Dimeric Annulation for the Tunable Synthesis of Thiazoles and 1,2,4-Thiadiazole

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5263 - 5268

Published: June 14, 2024

A green and sustainable electrochemical oxidative cyclization of enaminones with thioamides under metal- oxidant-free conditions has been developed, providing an efficient approach for thiazole synthesis. Furthermore, 1,2,4-thiadiazoles can be selectively accessed via the dimerization in absence enaminones.

Language: Английский

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An electrochemical-enabled cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(12), P. 4656 - 4661

Published: Jan. 1, 2023

An electrochemical-enabled three-component cascaded cyclization of enaminones with potassium thiocyanate and alcohols to access 2-alkoxythiazoles has been developed under external oxidant-free conditions.

Language: Английский

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The most Recent Compilation of Reactions of Enaminone Derivatives with various Amine Derivatives to Generate Biologically Active Compounds

Mini-Reviews in Medicinal Chemistry, Journal Year: 2023, Volume and Issue: 24(8), P. 793 - 843

Published: Sept. 14, 2023

Heterocyclic derivatives serve as the fundamental components of both natural and synthetic drugs. Enaminones play a crucial role foundational units in synthesis numerous bioactive heterocyclic compounds, including pyrazoles, pyridines, oxazoles, isoxazoles, well fused structures like indoles, carbazoles, quinolines, acridines, phenanthridines. These diverse rings are well-known for their various therapeutic activities, encompassing anticancer, anti-inflammatory, antimicrobial, antidepressant, antiviral properties. By reacting with nitrogenbased nucleophiles, enaminones can generate azoles, azines, systems. This study focuses on recent advancements enaminone reactions (a) nitrogen-based such aliphatic amines, aniline, hydroxylamine, hydrazine derivatives, guanidine urea, thiourea (b) electrophiles, diazonium salts. have led to wide range compounds from 2010 end 2022.

Language: Английский

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Design, Synthesis, Characterization and Exploration of Biological Efficacy of Iminothiazoline Sulfonamide Hybrids as Efficient Inhibitor of Carbonic Anhydrase

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 142331 - 142331

Published: April 1, 2025

Language: Английский

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Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(3)

Published: Jan. 17, 2024

Abstract Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis use iodine DMSO in various synthetic routes for preparation valuable targets presented. These reduce acceptance on expensive additives reagents, offer more sustainable solution these scaffolds.

Language: Английский

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A Simple Approach to the Synthesis of 5-Aroyl-2-imino-2,3-dihydrothiazoles

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(2), P. 292 - 296

Published: Feb. 1, 2024

Language: Английский

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An In‐Depth Review on Recent Progress in Synthetic Approaches and Biological Activities of Thiazol‐2(3H)‐Imine Derivatives

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(32)

Published: Aug. 22, 2024

Abstract This review presents the in‐dept analysis of synthetic approaches towards thiazol‐2( 3H )‐imine and embarks at its various biological properties published during 2000 to 2023. The most important method synthesis involves reaction substituted thioureas α‐halo carbonyl compounds, condensation nucleophilic addition 2‐amino‐1,3‐thiazoline with aldehydes. Additionally, isothiocyanate‐based multicomponent synthesis, α‐nitroepoxides have been proved as benign precursors for this motif. Several eco‐friendly solvent‐free from diazonium salts, acetylenes, tertiary enaminones thiosemicarbazides also reported. epitome is a unique combination methods well activities like anti‐inflammatory, anti‐bacterial, anti‐cancer, anti‐leishmanial, anti‐microbial, herbicidal, anti‐HIV, may be valuable tool researchers tailor procedures according specific target structures applications. Moreover, enlightens applications platelet GPIIB/IIIA receptor antagonists, alkaline phosphatase inhibitors, neurodegenerative drug Pifithrin‐α analogues, skin whitening agents.

Language: Английский

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NBS-Promoted Synthesis of Thiocyanated Aminomaleimides and Site-Selective Intramolecular Cyclization Access to 1,4-Benzothiazepines via S–CN Bond Cleavage

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5266 - 5276

Published: April 9, 2024

A transition metal-free concise and efficient protocol for the synthesis of thiocyanated aminomaleimides benzo[e][1,4]thiazepine derivatives has been developed. The method involves an initial α-C–H thiocyanation with KSCN TEMPO-mediated tandem S–CN bond cleavage/intramolecular cyclization substitution processes, which enables formation seven-membered S/N-heterocycles. This synthetic strategy provides a reliable biologically interesting by using as sulfur sources well expands application enaminones reactions in heterocycles synthesis.

Language: Английский

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Iodine‐Mediated Three‐Component Strategy to Synthesize 2‐Aminothiazoles from β‐Diketones/β‐ketoesters, Arylamines and Ammonium Thiocyanate

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(46)

Published: Nov. 10, 2022

Abstract A one‐pot, three‐component protocol for the synthesis of 2‐aminothiazoles promoted by iodine from readily available starting materials such as β‐diketones/β‐ketoesters, arylamines, and NH 4 SCN has been developed. wide range arylamines was tolerated well to produce expected polysubstituted in moderate good yields. The characteristic features this methodology include operational ease, metal‐free reaction conditions, gram‐scale scalability, functional group tolerance, short times.

Language: Английский

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