Visible-Light-Mediated Rose Bengal- or [Ru(bpy)₃]²⁺-Catalyzed Radical [4 + 2] Cycloaddition: An Efficient Route to Tetrahydrocarbazoles

ACS Omega, Год журнала: 2025, Номер 10(10), С. 10713 - 10723

Опубликована: Март 7, 2025

A visible-light-induced Rose Bengal- or [Ru(bpy)3]2+-catalyzed radical [4 + 2] cycloaddition of redox-active indole N-hydroxyphthalimide esters with electron-deficient alkenes has been developed. This base-free protocol provides a facile and powerful route for the synthesis functionalized biologically significant tetrahydrocarbazoles under mild conditions. On one hand, when an organic photocatalyst-Rose Bengal was employed green light, desired were obtained in up to 82% yield. other reaction yield increased 93% presence [Ru(bpy)3Cl2]·6H2O blue light. The success gram-scale transformation experiments, as well photopromoted [5 further highlight practicality robustness this protocol. Mechanistic studies also support generation crucial alkyl intermediate.

Язык: Английский

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Ionic Liquid-Assisted Approaches in the Synthesis of Nitrogen-Containing Heterocycles: A Focus on 3- to 6-Membered Rings

Journal of Ionic Liquids, Год журнала: 2025, Номер unknown, С. 100146 - 100146

Опубликована: Март 1, 2025

Язык: Английский

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Rearrangement and Cyclization of Enamine Thianthrenium Salts: Effective Access to Substituted Indoles

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 2, 2025

A facile base-mediated cyclization and rearrangement of enamine thianthrenium salts for the construction indole compounds is disclosed. In this reaction, sequential cleavage two C-S bonds subsequent formation C-N C-C furnish a series substituted indoles in moderate to good yields. Furthermore, an efficient late-stage functionalization established. The method features wide substrate scope, functional group tolerance, low-cost starting materials.

Язык: Английский

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Carbazole derivatives as antioxidant and anticorrosion materials

Results in Chemistry, Год журнала: 2024, Номер 9, С. 101667 - 101667

Опубликована: Июль 1, 2024

In this study, a series of new carbazole derivatives were studied using several reactions, including the Vilsmeier–Haack reaction. A cyclization reaction within bromoacetic acid was reported to synthesize thiazolidinone compounds, followed by Mannich reacting prepared compound with formaldehyde and secondary amines, that is, diphenylamine, morpholine, phthalimide. All synthesized compounds characterized infrared spectroscopy, liquid chromatography–mass spectrometry, 1H 13C nuclear magnetic resonance spectroscopy. The antioxidant activities all free-radical scavenging method 2,2-diphenyl-1-picrylhydrazyl, demonstrating their moderate activity compared ascorbic as standard substance. effectiveness corrosion inhibitors in an acidic medium sulfuric (0.25 mol/L) electrochemical method. Acceptable corrosion-inhibition efficiency achieved, highest inhibition rate 55.21 % for VII.

Язык: Английский

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Synthesizing Chiral Hydrocarbazoles with a Tetrasubstituted Carbon Using Holmium-Catalyzed Enantioselective [4 + 2] Cycloaddition: Mechanistic Insights from Luminescence and DFT Studies

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 8305 - 8310

Опубликована: Май 22, 2024

This study analyzes the feasibility of utilizing catalytic and enantioselective [4 + 2] cycloaddition sterically demanding heterocycle-incorporated siloxydienes to yield polycyclic skeletons with a tetrasubstituted carbon. A catalyst derived from lanthanide triflimide enabled reaction. The mechanistic investigations transformations adducts are also discussed. proposed approach facilitates synthesis intricate polysubstituted skeletons, each multiple contiguous chiral centers, thereby aiding in production diverse hydrocarbazoles for drug discovery purposes.

Язык: Английский

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Programmable C–N Bond Formation through Radical‐Mediated Chemistry in Plasma‐Microdroplet Fusion

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Abstract Non‐thermal plasma discharge produced in the wake of charged microdroplets is found to facilitate catalyst‐free radical mediated hydrazine cross‐coupling reactions without use external light source, heat, precious metal complex, or trapping agents. A plasma‐microdroplet fusion platform utilized for introduction reagent that undergoes homolytic cleavage forming intermediate species. The non‐thermal causes originates from a chemically etched silica capillary. coupling intermediates gives various products. Plasma‐microdroplet occurs online programmable reaction allowing direct process optimization and product validation via mass spectrometry. applied herein with variety substrates, enabling i) self‐coupling form secondary amines identical N‐substitutions, ii) afford amine different N‐substituents, iii) followed by situ dehydrogenation give corresponding aryl‐aldimines two unique iv) cascade heterocyclic carbazole derivatives formation. These were made possible microdroplet environment through our ability program conditions such as concentration (i. e., flow rate), reactivity presence absence plasma), timescale operational mode source). selected implemented co‐axial spray format, which be advantageous over conventional one‐pot single emitter electrospray‐based reactions.

Язык: Английский

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Five-membered ring systems: Pyrroles and benzo analogs

Progress in heterocyclic chemistry, Год журнала: 2024, Номер unknown, С. 123 - 173

Опубликована: Янв. 1, 2024

Язык: Английский

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