Graphitic carbon nitride materials in dual metallo-photocatalysis: a promising concept in organic synthesis

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(9), P. 3374 - 3397

Published: Jan. 1, 2023

Discussion of the recent reports on dual metallo-photocatalytic strategies using graphitic carbon nitride materials in organic syntheses.

Language: Английский

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Visible-light driven electron–donor–acceptor (EDA) complex-initiated synthesis of thio-functionalized pyridines

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(51), P. 7990 - 7993

Published: Jan. 1, 2023

A visible/solar-light-induced electron-donor-acceptor (EDA)-aggregated/mediated radical cyclization between (E)-2-(1,3-diarylallylidene)malononitriles and thiophenols leads to poly-functionalized pyridines. The two reacting partners form an EDA complex that absorbs light triggers the single-electron transfer (SET) generate a thiol radical, which undergoes addition/cyclization with dicyanodiene through formation of C-S C-N bonds.

Language: Английский

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Palladium-Catalyzed Asymmetric Acetoxylative Cyclization/Acyl Transfer Cascade of Alkyne-Tethered Malononitriles with Carboxylic Acids

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

Published: Feb. 2, 2025

Palladium-catalyzed asymmetric intermolecular trans-acetoxypalladation/desymmetric cyclization/acyl transfer cascades of alkyne-tethered malononitriles with carboxylic acids have been demonstrated. Such a sequence enables the formation multifunctionalized nitriles bearing α-all-carbon quaternary stereocenters high degree enantiocontrol broad substrate scope. Moreover, synthetic elaborations present these molecules as promising chiral building blocks. Mechanistic studies illustrate that cascade process proceeds via key imine intermediate, and desymmetric cyclization is enantio-determining step.

Language: Английский

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Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles

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

Published: March 11, 2025

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)4BF4 and Ag2CO3 in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, is assumed proceed via enamine formation, intramolecular cyclization, rearrangement. potential methodology also demonstrated for a gram-scale as well some useful organic transformations. offers practical pathway achieve polysubstituted broad substrate scope good functional group tolerance.

Language: Английский

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Pd(II)-Catalyzed Three-Component Synthesis of Furo[2,3-d]pyrimidines from β-Ketodinitriles, Boronic Acids, and Aldehydes

Organic Letters, Journal Year: 2023, Volume and Issue: 25(50), P. 9070 - 9075

Published: Dec. 13, 2023

A Pd(II)-catalyzed three-component synthesis of 2,4,6-triarylfuro[2,3-d]pyrimidines from β-ketodinitriles, boronic acids, and aldehydes has been developed. The participation both nitrile (-CN) groups led to the concurrent construction furo-pyrimidine via formation C-C, C═C, C-O, C-N, C═N bonds. compounds show excellent photoluminescence properties with absorption maxima ranging 348 387 nm emission 468 533 nm. synthetic utility protocol was further demonstrated through a few postsynthetic manipulations.

Language: Английский

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Organic Base-Promoted C–N- and C–O-Coupled Domino Cyclization Strategy: Syntheses of Oxazine-6-ones and 4-Pyrimidinols

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5650 - 5664

Published: April 5, 2024

Oxazine-6-one and 4-pyrimidinol are two important frameworks in pharmaceutical production. Herein, we disclosed a simple, efficient, inexpensive organic base-promoted additive-stimulated protocol for the syntheses of variably functionalized oxazine-6-ones 4-pyrimidinols employing acetonitrile solvent under conventional heating conditions using an oil bath through C–N C–O coupled domino steps. This simple practicable productive utilizes easily producible cheap precursors, namely, benzimidates or benzamidines, with differently substituted dicyano-olefins, it comprises step economy, robustness, moisture insensitive affording high yield that avoids use transition-metal catalysts, multistep multicomponent strategy, harsh reaction involving hazardous chemicals. method is scalable into gram-scale production good yield.

Language: Английский

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Solvent Dictated Organic Transformations

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

Solvent plays an important role in many chemical reactions. The C-H activation has been one of the most powerful tools organic synthesis. These reactions are often assisted by solvents which not only provide a medium for but also facilitate reaching to product stage. solvent helps reaction profile both chemically and energetically reach targeted product. Organic transformations via from assistance perspective discussed this review. Various such as tetrahydrofuran (THF), MeCN, dichloromethane (DCM), dimethoxyethane (DME), 1,2-dichloroethane (1,2-DCE), dimethylformamide (DMF), dimethylsulfoxide (DMSO), isopropyl nitrile (

Language: Английский

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Six-membered ring systems: Pyridines and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 309 - 354

Published: Jan. 1, 2024

Language: Английский

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