N¹-Allylation of Arylhydrazines via a Palladium-Catalyzed Allylic Substitution

Organic Letters, Год журнала: 2023, Номер 25(26), С. 4880 - 4885

Опубликована: Июнь 22, 2023

A direct and efficient method for constructing N,N-disubstituted hydrazines via a palladium-catalyzed allylic substitution of allyl acetates with arylhydrazines as nucleophiles has been developed. This is highly selective in terms both chemo- regio-selectivity carried out under an open-air system the use DPPPy phosphine ligand. Additionally, this reaction compatible wide variety substrates, including those bearing reactive groups such Cl, Br, I, to afford various N1-allylation products moderate good yields simple mild conditions.

Язык: Английский

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Metal-Controlled Switchable Regioselective Synthesis of Substituted Imidazoles and Pyrroles via Ring Opening/Cyclocondensation with 2H-Azirines

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 9811 - 9822

Опубликована: Июль 4, 2023

Catalytic selective annulation of 2H-azirines constitutes a general and modular strategy for the generation molecular complexity. By using Pd-catalyzed ring opening/heterocyclization associated with direct cleavage C–N C–C bonds under appropriate conditions, formation imidazoles is presented. Alternatively, silver-catalyzed radical [3 + 2] cycloannulation 1,3-dicarbonyl compounds provides highly functionalized pyrrole derivatives. Both aliphatic cyclic acyclic diketones are tolerated good regioselectivity. Moreover, capture experiment was carried out to determine proposed mechanism, providing support facile process.

Язык: Английский

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Palladium–Copper-Catalyzed Oxidative Intermolecular [2 + 2 + 2] Coupling–Annulation: Regioselective Synthesis of Multiaryl-Substituted Benzenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4579 - 4594

Опубликована: Март 20, 2024

A palladium-catalyzed intermolecular [2 + 2 2] oxidative coupling–annulation of terminal alkenes and alkynes using copper(II) as the oxidant has been developed through direct C–C bond formation. These reactions provide effective access to multiaryl-substituted benzenes with high regioselectivity in absence any ligands. The features this protocol are broad substrate scope, atom step economy. aggregation-induced emission properties selected products were further investigated. synthesized may be worth exploring for applications fields advanced functional materials or drugs.

Язык: Английский

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Copper-Catalyzed Domino-Double Annulation of o-Aminobenzamides with 2-Iodoisothiocyanates for the Synthesis of 12H-Benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 4774 - 4783

Опубликована: Март 20, 2024

A facile and efficient copper-catalyzed domino-double annulation strategy was developed from easily accessible o-aminobenzamides 2-iodoisothiocyanates, which affords a direct pathway for the synthesis of tetracyclic fused 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones in moderate to good yields without addition ligands, bases, external oxidants. The reaction involves C–N bond cleavage formation C–N/C–S one step with advantages using an inexpensive copper catalyst easy operation. Mechanistic studies suggest that this transformation proceeds via intermolecular condensation followed by intramolecular Ullmann-type cross-coupling cyclization reaction.

Язык: Английский

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Visible-light-driven three-component annulation for the synthesis of highly functionalized 2-iminothiazolidin-4-ones without photocatalysts

Green Chemistry, Год журнала: 2024, Номер 26(8), С. 4477 - 4483

Опубликована: Янв. 1, 2024

A photocatalyst/base/metal-free protocol for the synthesis of fully substituted 2-iminothiazolidin-4-one derivatives at room temperature using low-energy light sources and mild reaction conditions is described.

Язык: Английский

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Synthesis of N,N‐Disubstituted Hydrazines by Electrocatalytic Addition of Hydrazines to α,β‐Unsaturated Carbonyl Compounds

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2829 - 2834

Опубликована: Апрель 24, 2024

Abstract A strategy for the synthesis of N,N ‐disubstituted hydrazines via electrocatalytic addition hydrazine to α,β‐unsaturated carbonyl compounds is reported. The reaction was carried out under constant current electrolytic conditions in an undivided cell. Using this methodology, various were prepared 57–94% yield 40 minutes. By adding cyclohexanone and acetic acid mixture heating 2 hours, a one‐pot N ‐substituted indoles also developed. Furthermore, based on cyclic voltammetry control experiments, plausible mechanism involving radical pathway proposed.

Язык: Английский

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Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh₃/DDQ System

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10054 - 10065

Опубликована: Июль 1, 2024

We present a PPh3/DDQ-mediated regiospecific selective N-functionalization of arylhydrazines with primary benzylic alcohols and aryl carboxylic acids for the synthesis N1-benzyl N2-acyl arylhydrazines, respectively. This metal- base-free approach features very short reaction times (about 10 min), broad substrate scope, good functional group tolerance, mild conditions. Furthermore, N1-benzlated products have also been successfully applied to concise N-substituted indoles anticancer drug MDM2 inhibitor.

Язык: Английский

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Recent Highlights in the Synthesis and Biological Significance of Pyrazole Derivatives

Heliyon, Год журнала: 2024, Номер 10(20), С. e38894 - e38894

Опубликована: Окт. 1, 2024

Язык: Английский

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Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16809 - 16827

Опубликована: Ноя. 1, 2024

A photocatalytic three-component cascade reaction of readily available enaminones, hydrazines, and CBr4 for the synthesis bromo-substituted pyrazoles in one pot has been demonstrated. This strategy involves intermolecular C-N/C-Br bond formation represents an efficient approach to construction 4-bromo-substituted with high regioselectivity, broad substrate scope, good functional group tolerance, convenient operation, mild conditions. Mechanistic investigations show that this proceeds via cyclization enaminones followed by a regioselective bromination using as "Br" source.

Язык: Английский

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(E)-2-Methoxyethene-1-sulfonyl fluoride as a precursor of acetylene for synthesis of C₁/C₂ non-functionalized pyrrolo[2,1-a]isoquinoline derivatives

New Journal of Chemistry, Год журнала: 2023, Номер 47(35), С. 16332 - 16336

Опубликована: Янв. 1, 2023

A exclusive synthesis of pyrrolo[2,1- a ]isoquinoline derivatives involving ( E )-2-methoxyethene-1-sulfonyl fluoride (MESF) and isoquinolinium N -ylides is described variety C 1 /C 2 non-functionalized ]isoquinolines were prepared.

Язык: Английский

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