Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(52)

Published: June 28, 2023

Abstract Selenium, originally described as a toxin, turns out to be crucial trace element for life that appears selenocysteine and its dimer, selenocystine. From the point of view drug developments, selenium‐containing drugs are isosteres sulfur oxygen with advantage presence selenium atom confers antioxidant properties high lipophilicity, which would increase cell membrane permeation leading better oral bioavailability. In this article, we have focused on relevant features atom, above all, corresponding synthetic approaches access variety organoselenium molecules along proposed reaction mechanisms. The preparation biological selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, other compounds will treated. We attempted condense most important aspects interesting examples chemistry into single article.

Language: Английский

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Sustainable electrochemical cross-dehydrogenative coupling of 4-quinolones and diorganyl diselenides

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2021, Volume and Issue: 42(9), P. 1445 - 1450

Published: May 6, 2021

Language: Английский

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Electrochemical Functionalization of Imidazopyridine and Indazole: An Overview

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(22), P. 5047 - 5071

Published: Oct. 1, 2021

Abstract Electrochemical synthesis offers a mild, simple, and efficient tool for the preparation of interesting useful molecules, thus eluding severe chemical oxidizing reducing agents used in conventional synthetic methods. In particular, electrochemical C−H activation is expected to play an important role direct functionalization heterocyclic compounds. Over past few decades, research interest imidazopyridine indazole has increased significantly due their multipurpose uses medicinal industrial chemistry. Therefore, structural modification these heterocycles using electro‐oxidation become one topics among organic chemistry recent time. This review provides comprehensive discussion indazoles imidazopyridines published so far. A summary current challenges future direction development green methods also presented. magnified image

Language: Английский

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Regioselective C–H Sulfonylation of 2H-Indazoles by Electrosynthesis

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(5), P. 3699 - 3708

Published: Jan. 31, 2020

This study reveals a transition-metal- and external oxidant-free electrochemical method for the C3–H sulfonylation of biologically diverse 2H-indazoles at room temperature under ambient air. Using various sulfonyl hydrazides as precursor, series sulfonylated indazole derivatives containing broad spectrum functional groups were synthesized in up to 92% yield. Mechanistic studies suggest precedented radical pathway is operating process.

Language: Английский

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Direct Catalytic Functionalization of Indazole Derivatives

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(18), P. 3768 - 3794

Published: May 28, 2020

Abstract Indazoles are a very important class of N‐containing heterocycles with wide range biological and medicinal properties. The presence different functionalities on indazole moieties enhances its activities. Hence, the preparation compounds bearing functional groups has gained significant interest to organic synthetic chemists. A large effort been made develop efficient new methods for functionalization indazoles. Direct catalytic is powerful tool facile synthesis derivatives due straightforwardness. This review summarizes developments direct functionalizations indazoles published in last two decades. magnified image

Language: Английский

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Electrochemical Radical–Radical Cross-Coupling Approach between Sodium Sulfinates and 2H-Indazoles to 3-Sulfonylated 2H-Indazoles

Organic Letters, Journal Year: 2020, Volume and Issue: 22(16), P. 6319 - 6323

Published: Aug. 5, 2020

A direct cross-coupling between sodium sulfinates and 2H-indazoles has been developed under electrochemical conditions. The utilization of a graphite anode platinum cathode in an undivided cell with constant current 7 mA allowed the concurrent oxidations to sulfonyl radical cationic 2H-indazoles, facilitating radical-radical coupling strategy 3-sulfonylated 2H-indazole derivatives. transition-metal- redox-reagent-free synthetic approach should serve as valuable tool achieve heteroaromatic compounds.

Language: Английский

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Visible light-induced functionalization of indazole and pyrazole: a recent update

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(28), P. 4435 - 4455

Published: Jan. 1, 2022

Indazole and pyrazole are renowned as a prodigious class of heterocycles having versatile uses in medicinal well industrial chemistry. Considering sustainable approaches, recently, photocatalysis has become an indispensable tool organic chemistry due to its application for the activation small molecules use clean energy source. In this review, we have highlighted metal-based photocatalysts, photoredox catalysts, transfer photocatalysts electron-donor-acceptor complexes functionalization indazole pyrazole. This perspective is arranged based on types reactions A detailed discussion regarding reaction mechanism each given provide comprehensive guide reader. Finally, summary existing challenges future outlook towards development efficient photocatalytic methods these also presented.

Language: Английский

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Organoselenium compounds in medicinal chemistry

ChemMedChem, Journal Year: 2024, Volume and Issue: 19(17)

Published: May 23, 2024

Abstract The chemical and biological interest in this element the molecules bearing selenium has been exponentially growing over years. Selenium, formerly designated as a toxin, becomes vital trace for life that appears selenocysteine its dimeric form, selenocystine, active sites of selenoproteins, which catalyze wide variety reactions, including detoxification reactive oxygen species modulation redox activities. From point view drug developments, organoselenium drugs are isosteres sulfur‐containing oxygen‐containing with advantage presence atom confers antioxidant properties high lipophilicity, would increase cell membrane permeation leading to better oral bioavailability. This statement is paramount relevance considering big number clinically employed compounds sulfur or atoms their structures nucleosides carbohydrates. Thus, article we have focused on relevant features application medicinal chemistry. With increasing chemistry, attempted highlight most significant published data subject, mainly concentrating analysis last In consequence, recent advances pharmacological discussed.

Language: Английский

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Electrochemical diselenylation of indolizines via intermolecular C–Se formation with 2-methylpyridines, α-bromoketones and diselenides

Chemical Communications, Journal Year: 2019, Volume and Issue: 56(5), P. 735 - 738

Published: Dec. 6, 2019

An efficient electrochemical system for the construction of diselenytlated indolizines from available pyridines, ketones and diselenides under undivided electrolytic conditions was developed. No external oxidants transition-metal catalysts are needed achieving this three-component tandem reaction realizing C-C, C-N C-Se bond formations.

Language: Английский

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Visible Light-Mediated C(sp²)–H Selenylation of Amino Pyrazole and Amino Uracils in the Presence of Rose Bengal as an Organophotocatalyst

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(2), P. 1230 - 1239

Published: Jan. 7, 2022

Herein, we report an efficient methodology for the synthesis of alkyl, benzyl, and phenyl selenoethers aminopyrazoles aminouracils by C(sp2)-H functionalization in presence visible light Rose Bengal as organophotocatalyst. The reaction amino pyrazole/iosothiazole/isoxazole or uracils with 0.5 equivalent diphenyl/dibenzyl/diethyl diselenides acetonitrile medium a catalytic amount provided corresponding phenyl, ethyl good to very yields. We have also utilized some selenylated preparation pyrazole-fused dihydropyrimidines tethered arylselenoethers catalyst-free one-pot three-component reaction. notable features this are metal-free conditions, yields, use organic photocatalyst, wide substrate scope; it is applicable gram-scale provides medicinally important heterocycles such amio-pyrazole, isoxazole, isothiazole, uracils.

Language: Английский

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