Seven-membered N-heterocycles as approved drugs and promising leads in medicinal chemistry as well as the metal-free domino access to their scaffolds

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 275, P. 116556 - 116556

Published: June 5, 2024

Azepanes or azepines are structural motifs of many drugs, drug candidates and evaluated lead compounds. Even though compounds having N-heterocyclic 7-membered rings often found in nature (e.g. alkaloids), the natural this group rather rare as approved therapeutics. Thus, recently studied azepane azepine-congeners predominantly consist semi-synthetically synthetically-obtained scaffolds. In review a comparison drugs investigated leads was proposed taking into regard their aspects (stereochemistry), biological activities, pharmacokinetic properties confirmed molecular targets. The N-heterocycles reveal wide range not only against CNS diseases, but also e.g. antibacterial, anticancer, antiviral, antiparasitic allergy agents. As most potential structures, belonging to N-heterocycles, synthetic scaffolds, report reveals different efficient metal-free cascade approaches useful synthesize both simple azepine-containing congeners those oligocyclic structures. Stereochemistry azepane/azepine fused systems, view data binding with targets, is discussed. Apart from we compare advances SAR studies (mainly 2018 2023), whereas related part concerning various domino strategies focused on last ten years.

Language: Английский

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Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

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Electrochemical Cyclizative Carboxylation of Alkene-Tethered Aryl Isocyanides with Carbon Dioxide

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

Herein, we present an unprecedented electrochemical reductive cyclizative carboxylation of o-vinylphenyl isocyanides with carbon dioxide achieved without the use metal catalysts. This protocol demonstrates a broad substrate scope and good functional group tolerance, facilitating rapid assembly 2-oxoindolin-3-acetic acids in to high yields excellent regioselectivity. Furthermore, these structural motifs may have potential applications formal synthesis bioactive natural products.

Language: Английский

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Selective Construction of 2,4-Bisthioquinolines via Copper-Catalyzed Tandem Cyclization from o-Alkynylphenyl Isothiocyanates

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

The selective synthesis of polysubstituted quinoline has been recognized as an important but highly challenging transformation. In this study, a efficient method for the 2,4-bisthioquinolines developed through copper(II)-promoted tandem cycloaddition o-alkynylphenyl isothiocyanates, utilizing inexpensive and readily available sodium sulfide (Na2S) sulfur source. This transformation enables direct 2,4-bis(thioquinoline) heterocycles via formation C-C C-S bonds in one-pot reaction, demonstrating excellent tolerance various functional groups.

Language: Английский

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Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Language: Английский

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Visible Light-Induced Tandem Radical Cyclization for the Synthesis of 2-(3-Cyanoalkyl)Substituted Quinoline Derivatives

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

A highly efficient 6-endo-trig radical cyclization reaction between cyclobutanone oximes and 1-isocyano-2-vinylbenzenes via visible light-induced photoredox catalysis has been realized in the presence of 2 mol % fac-Ir(ppy)3 as photocatalyst, which gave rise to a variety 2-(3-cyanoalkyl)substituted quinoline derivatives with moderate excellent yields under mild conditions.

Language: Английский

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Iodine‐Mediated Regioselective Radical Cyclization of o‐Vinylaryl Isocyanides with Disulfides/Diselenides Leading to 2‐Chalcogenated Quinolines

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3814 - 3818

Published: Sept. 26, 2023

Abstract An iodine‐mediated radical cyclization of o ‐vinylaryl isocyanides with disulfides or diselenides was developed. The atom‐economic reaction provides a method for regioselective construction the 2‐chalcogenated quinolines in 42–93% yields by incorporation both chalcogen atoms into quinolines.

Language: Английский

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Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8149 - 8153

Published: Sept. 16, 2024

Indole and quinoline structures are present in numerous biologically active molecules, making the synthesis of their glycosylation products a subject extensive research interest drug development. Here, we report photoredox strategy for

Language: Английский

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FeF₃‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(30)

Published: April 24, 2024

Abstract An iron(III)‐promoted radical fluoroalkylation of o‐alkenylaryl isocyanides has been developed using readily available perfluoroalkyl iodides as fluoroalkyl source. This cyclization reaction features broad substrate scope and provides a simple efficient approach for regioselective construction biologically important 2‐fluoroalkylated quinolines in 38–81 % yields.

Language: Английский

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Metal-Free Photoinduced-Radical Hydrocyclization of 2-Isocyanides: A Unified Synthetic Approach to Facilely Assemble Diverse N-Heteroarenes

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(21), P. 10804 - 10810

Published: Jan. 1, 2024

We present an efficient and sustainable protocol for the photoinduced-radical hydrocyclization of isocyanides, providing a united route to assemble diverse α-unsubstituted N-heteroarenes.

Language: Английский

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