Divergent Synthesis of Four Types of Fused N‐Containing Heterocycles via Oxidative Multi‐Component Cyclization Reaction

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 31, 2025

Comprehensive Summary An atmospheric‐oxygen‐mediated four‐component reaction was developed for the divergent synthesis of pyrazolo[1,5‐ a ]pyrimidine and pyrazolo[3,4‐ b ]pyridine derivatives from readily available alcohols 3‐aminopyrazoles. In this transformation, atmospheric oxygen serves as green oxidant, promoting equivalent aldehydes four types N ‐containing heterocycles (> 40 examples). Remarkably, transformation features metal‐free molecular diversity.

Language: Английский

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Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7425 - 7430

Published: Aug. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Language: Английский

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Visible‐Light‐Induced Domino Cyclization to Access Pyrido[2,3‐d]pyrimidine‐2,4‐diones via a Radical‐Polar Crossover Reaction

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(19), P. 2346 - 2350

Published: May 27, 2024

Comprehensive Summary Catalytic and green strategies for the synthesis of privileged scaffolds are synthetically appealing. We now report a radical‐polar crossover (RPC)‐enabled three‐component cyclization bromodifluoroalkyls with enaminones 6‐aminouraciles via visible‐light‐induced domino cyclization. The reaction exhibited broad substrate scope (> 40 examples) including complex molecules, which highlighted utility this strategy construction library bioactive analogs.

Language: Английский

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Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4214 - 4218

Published: Jan. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Language: Английский

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Synthesis of CF₃-Azafluorenes through the Cascade Reaction of 2H-Imidazoles with CF₃-Ynones

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

Published: Nov. 25, 2024

A concise synthesis of trifluoromethyl (CF

Language: Английский

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Photocatalytic Synthesis of Isoquinolinediones via the Cascade Reaction of N-Alkyl-N-methylacrylamides with Diazo Compounds

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

Published: March 25, 2025

Carbon radicals generated from acceptor diazo compounds prefer to add electron-rich olefins and heteroarenes due their containing electron-withdrawing groups. Herein, a cascade reaction of with electron-deficient is developed. In the presence visible light Ru catalyst, generate carbon via proton-coupled electron transfer process, followed by addition various N-alkyl-N-methylacrylamides subsequent cyclization give series acyl-substituted isoquinolinediones.

Language: Английский

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BPO-promoted [4 + 2] cyclization of enaminones and o-phenylenediamines to 2-acyl quinoxalines via a cascade transamination and C–H amination

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(20), P. 4067 - 4071

Published: Jan. 1, 2024

Rapid assembly of quinoxalines in a single step from readily available precursors has been recognized as an ideal platform terms efficiency and operation. Herein, we report BPO-promoted metal-free approach to 2-acyl enaminones

Language: Английский

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N-Benzylhydroxylamine as a novel synthetic block in “C1N1” embedding reaction via α-C(sp³)–H activation strategy

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(56), P. 7180 - 7183

Published: Jan. 1, 2024

A novel process using N -benzylhydroxylamine hydrochloride as a “C1N1 synthon” in [2+2+1] cyclization for the construction of 1,2,5-trisubstituted imidazoles has been described first time.

Language: Английский

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Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans

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

Published: Sept. 27, 2024

A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4

Language: Английский

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Eco-Friendly alpha,beta-C(sp3)-H Difunctionalization of Tertiary Amines via Sequential [1,5]-Hydride Transfer and Hetero-Diels-Alder Cyclization

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(77), P. 10712 - 10715

Published: Jan. 1, 2024

An unprecedented eco-friendly multi-component domino reaction for the synthesis of novel

Language: Английский

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