Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7188 - 7198

Published: May 12, 2023

Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines quinolines. The selective products can be achieved by employing enaminones or enaminones/anilines reaction partners. In addition, compared with using conventional aldehyde synthons, rongalite displays an evident advantage in providing considerably higher product yields under milder conditions. GC-MS analysis process performed to probe possible mechanism.

Language: Английский

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Rongalite as a Versatile Reagent in Organic Synthesis^†

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(23), P. 3388 - 3400

Published: June 24, 2023

Comprehensive Summary This review provides a comprehensive summary of progress to date in the utilization rongalite as versatile reagent organic synthesis, with focus on recent researches. The contents have been organized according functions exhibited by rongalite. Reaction mechanisms are provided, demonstrating multifaceted roles this compound various transformations, including sulfone, C1 or masked proton source and single electron donor reducing agent.

Language: Английский

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Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7659 - 7664

Published: Oct. 10, 2022

An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2H-thiopyran 1,1-dioxides. Notably, rongalite acted as a tethered C-S synthon in this reaction and can be chemoselectively used triple C1 units source sulfone. Mechanistic investigation indicated that two different carbon-increasing models are involved which serves units.

Language: Английский

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Reductive N-Formylation of Nitroarenes Mediated by Rongalite

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7220 - 7224

Published: Sept. 28, 2023

Herein, we disclose a straightforward approach to access transition-metal-free reductive N-formylation of nitroarenes. This reaction integrates the dual role rongalite, which acts as reductant and C1 building block concurrently. provides an alternative method for synthesis N-aryl formamides from nitroarenes, including construction C–N bond. The utility this protocol was demonstrated by scale-up late-stage functionalizations complex molecules.

Language: Английский

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EPR/UV–Vis–NIR spectroelectrochemical characterization of 10H-phenothiazinyl-substituted oligothiophenes

Electrochimica Acta, Journal Year: 2025, Volume and Issue: unknown, P. 145714 - 145714

Published: Jan. 1, 2025

Language: Английский

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Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4340 - 4345

Published: May 14, 2024

An unconventional [1 + 1 1] annulation process was developed for the construction of β,β-dithioketones by merging C–C and C–S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur(II) synthons, a reductant first time. Mechanism investigation indicated that reaction involved self-mediated valence state change rongalite. By performing step-economical method, challenging C5-substituted 1,3-dithiane can be achieved under mild simple conditions.

Language: Английский

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Fast and efficient one-pot ultrasound-mediated synthesis of solid state (full color tunable) fluorescent indolizine derivatives

Dyes and Pigments, Journal Year: 2023, Volume and Issue: 216, P. 111332 - 111332

Published: April 24, 2023

Language: Английский

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Synthesis and biological evaluation of 5-chalcogenyl-benzo[h]quinolines via photocyclization of arylethynylpyridine derivatives

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(48), P. 23030 - 23038

Published: Jan. 1, 2022

A new method for the synthesis of benzo[ h ]quinolines 5-chalcogenyl-functionalized via visible light-promoted intramolecular ortho -cyclization was described. Furthermore, studies have suggested that this class compounds may promising therapeutic potential.

Language: Английский

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Efficient Synthesis of 2,5‐Disubstituted Chalcogenophenes by a One‐pot, Stepwise Glaser Coupling – Cycloaddition Sequence

ChemistrySelect, Journal Year: 2023, Volume and Issue: 8(38)

Published: Oct. 9, 2023

Abstract A mild and efficient method for the synthesis of 2,5‐disubstituted chalcogenophenes is reported. This involves two steps reactions via one‐pot approach by employing commercially available cost‐effective alkynes element chalcogen. Further, using LiNH 2 as promoter DMSO/EtOH solvent, Cu‐catalyzed Glaser coupling‐cycloaddition processes are dramatically enhanced that a diverse range can be obtained in good to excellent yields under conditions. Controlled experiments show trisulfur radical anion (S3⋅ − ) key intermediate serves hydrogen source, while alcohol may facilitate transition state.

Language: Английский

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Elucidating the electronic properties of 2,5-di(hetero)arylthiophenes bearing pyridine, thienyl, tolyl, and benzonitrile pending groups: An experimental and theoretical approach

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1321, P. 139899 - 139899

Published: Sept. 2, 2024

Language: Английский

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