Photochemical reactions as synthetic tool for pharmaceutical industries

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109498 - 109498

Published: Jan. 6, 2024

Language: Английский

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Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 4947 - 4957

Published: March 18, 2024

A photoredox/copper-catalyzed cascade radical cyclization/phosphorothiolation reaction of N-allylbromoacetamides and P(O)SH compounds has been established. broad range novel nonfluorine- or difluoro-substituted 2-pyrrolidinones bearing the C(sp3)-SP(O)(OR)2 moiety can be conveniently constructed in moderate to good yields under mild conditions. Importantly, most tested phosphorothiolated showed potent inhibitory effects toward both AChE BChE.

Language: Английский

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Photoinduced Three-Component Difluoroamidosulfonylation/Bicyclization: A Route to Dihydrobenzofuran Derivatives

Organic Letters, Journal Year: 2022, Volume and Issue: 24(13), P. 2556 - 2561

Published: March 29, 2022

A visible-light-induced photocatalyst-free three-component radical cascade bicyclization has been achieved to obtain diverse difluoroamidosulfonylated dihydrobenzofurans in moderate good yields. This protocol avoids potential toxicity and the tedious removal procedure for photocatalysts also features mild reaction conditions a functional group tolerance. Moreover, mechanistic investigations reveal formation of charge-transfer complex involvement an intramolecular 1,5-hydrogen atom transfer process this transformation.

Language: Английский

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Visible-Light-Induced, Palladium-Catalyzed Annulation of 1,3-Dienes to Construct Vinyl N-Heterocycles

Organic Letters, Journal Year: 2022, Volume and Issue: 24(29), P. 5407 - 5411

Published: July 18, 2022

Herein, a photoinduced palladium-catalyzed annulation of 1,3-dienes with bifunctional halognated alkylamines has been developed, offering facile route to access broad range vinylpyrrolidines. The reactivity profile this protocol was able be readily manipulated assemble vinylpyrrolidine and vinlysilaazacycle. Remarkably, the utility strategy further illustrated in construction complex biologically important molecules as well diversity-oriented transformations resulting product.

Language: Английский

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Photoinduced Three‐Component Cyclization of Arylamines, Enaminones and Difluorobromoacetates to 2,3‐Difunctionalized Quinolines

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(20), P. 3539 - 3543

Published: Aug. 26, 2022

Abstract A photoinduced multicomponent reaction of arylamines, enaminones and difluorobromoacetates for the synthesis 2,3‐difunctionalized quinolines is reported. This strategy features broad functional groups tolerance wide substrate scopes that enables further synthetic applications obtained products. Mechanistic studies reveal intermolecular [3+3] cyclization between in‐situ generated 1,3‐vinylimine ions arylamines key step in this transformation. magnified image

Language: Английский

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Photocatalytically switchable chemoselective difluoramidation of olefins for the synthesis of diversified difluoro-γ-lactams

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This study demonstrates a visible-light-driven intramolecular alkene difluorination enabling Heck-type coupling, hydrofluoramidation, and difunctionalization. Diverse difluoro-γ-lactams were synthesized with high selectivity substrate generality.

Language: Английский

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Visible Light-Promoted Radical Relay Cyclization/C–C Bond Formation of N-Allylbromodifluoroacetamides with Quinoxalin-2(1H)-ones

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 17173 - 17183

Published: Nov. 6, 2021

A visible light-promoted radical relay of N-allylbromodifluoroacetamide with quinoxalin-2(1H)-ones was developed in which 5-exo-trig cyclization and C–C bond formation were involved. This protocol performed under mild conditions to facilely offer a variety hybrid molecules bearing both quinoxalin-2(1H)-one 3,3-difluoro-γ-lactam motifs. These prepared novel skeletons would expand the accessible chemical space for structurally complex heterocycles potential biological activities.

Language: Английский

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Visible‐light‐promoted Radical Cyclization/Arylation Cascade for the Construction of α,α‐Difluoro‐γ‐Lactam‐Fused Quinoxalin‐2(1H)‐Ones

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 40(6), P. 713 - 718

Published: Dec. 10, 2021

Comprehensive Summary A visible‐light‐induced tandem radical intramolecular cyclization/arylation of quinoxalin‐2(1 H )‐ones with bromodifluoroacetamides is described. This protocol allows efficient access to a variety valuable α,α ‐difluoro‐ γ ‐lactam‐fused in moderate good yields under metal‐free, mild and redox neutral reaction conditions. strategy tolerant various functional groups broad range substrates. The mechanism experiments suggested an involvement 5‐ exo ‐trig cyclization process this transformation.

Language: Английский

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Light‐Induced Domino and Multicomponent Reactions: How to Reach Molecular Complexity without a Catalyst

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 31, 2023

Abstract Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over past decades, a lot efforts have been put on development photocatalytic cascades employing both metal‐based purely organic catalysts. Despite effectiveness these protocols, catalyst‐ additive‐free light‐induced are gaining momentum thank their efficiency, operational simplicity sustainability. The increasing number papers published field in last years is proof appeal transformations. In Review, we discuss multicomponent mediated by light with focus photocatalyst‐ processes. most recent advances synthesis complex nitrogen‐, oxygen‐, sulphur‐ selenium‐heterocycles together analysed emphasis experimental mechanistic studies.

Language: Английский

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Nickel-Catalyzed Cyclization/Carbonylation Reaction of N-Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones

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

Published: Jan. 24, 2025

A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of N-allylbromoacetamides toward the synthesis 2-pyrrolidinone derivatives has been developed with arylboronic acids as reaction partner. This proceeds through a sequential single-electron-transfer pathway via 5-exo-trig cyclization carbonyl insertion steps, furnishing variety in good yields. Various useful functional groups were well tolerated. Moreover, formic acid is applied CO source here nickel catalyst, which provides supplement for carbonylation chemistry heterocycle synthesis.

Language: Английский

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