Novel One-Pot Synthesis of Thiophenols from Related Triazenes under Mild Conditions

Khazaei, Ardeshir; Kazem‐Rostami, Masoud; Moosavi‐Zare, Ahmad Reza; Bayat, Mohammad; Saednia, Shahnaz

doi:10.1055/s-0032-1316557

Cited by 20 publications

(4 citation statements)

References 24 publications

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“…This scarcity may be attributed to the toxic nature of the simplest thiophenol. Nevertheless, thiophenol plays a crucial role as a fundamental component in various pharmaceutical products and antifungal agents [2,3]. As reported by Khazaei and colleagues [2], thiophenols find application in the production of pharmaceuticals, including sulfonamides.…”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, thiophenol plays a crucial role as a fundamental component in various pharmaceutical products and antifungal agents [2,3]. As reported by Khazaei and colleagues [2], thiophenols find application in the production of pharmaceuticals, including sulfonamides. Examples of common drugs derived from thiophenols include the antipsychotic agent Thioridazine [4], the antifungal Butoconazole [5], the anthelmintic Albendazole [6], and the old (1939s) antiseptic Merthiolate [7].…”

Section: Introductionmentioning

confidence: 99%

“…The intriguing chemistry of sulfur-centered radicals spans diverse fields such as organic synthesis, biochemistry, and environmental science, attracting considerable attention [1,2]. Numerous studies have focused on antioxidant compounds like polyphenols and flavonoids to assess their antioxidant capacity.…”

Section: Introductionmentioning

confidence: 99%

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Bond analysis in meta- and para-substituted thiophenols: overlap descriptors, local mode analysis, and QTAIM

Barbosa,

Santos-,

Andrade

et al. 2024

J Mol Model

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Context: This study delves into the chemical nuances of thiophenols and their derivatives through a comprehensive computational analysis, moving beyond traditional energetic perspectives such as bond dissociation enthalpy and S−H dissociation dynamics. By employing the overlap model along with its topological descriptors (OP/TOP), Quantum Theory of Atoms in Molecules (QTAIM), and Local Vibrational Mode (LVM) theories, the research provides a deeper understanding of the S−H and C−S bonding scenarios in substituted thiophenols. The investigation follows the electron-donating capacity of S−H substituent variation with the nature and positioning of other ring substituents. Energy profile analyses indicate distinct stability differences in the cis and trans conformations of meta-and para-PhSH systems, influenced by the electron-donating strength of these substituents. The study also uncovers significant variations in S−H bond distances and descriptor values, particularly in para-substituted PhSH, reflecting the influence of electron-donating or withdrawing substituents. In contrast, alterations at the meta-position show minimal effects on C−S bond descriptors, while para-substitutions markedly influence C−S bond characteristics, demonstrating a clear correlation with the electron-donating or withdrawing capabilities of the substituents. This research sheds light on the intricate bond dynamics in aromatic systems with diverse substituents, highlighting the complex interaction between electronic effects and molecular conformation. Methods: The study employs the ωB97X-D/Def2TZVP level of theory for molecular geometries, ensuring accurate characterization of structures as true minima via analytical harmonic frequency determination. The electronic properties of S−H and C−S bonds in variously substituted thiophenols were analyzed using OP/TOP, QTAIM, and LVM methodologies. Computational processes, including conformational scans, geometry optimizations, and vibrational frequency calculations, were conducted using Gaussian 09, with ultra-fine integration grids and tight convergence criteria for the SCF procedure. Bond descriptors were computed utilizing ChemBOS, Multiwfn, and LModeA software, providing a robust and detailed examination of bond properties. Chemical bond overlap densityElectron-donating group Electron-withdrawing group

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bond analysis in meta- and para-substituted thiophenols: overlap descriptors, local mode analysis, and QTAIM

Barbosa,

Santos-,

Andrade

et al. 2024

J Mol Model

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“…Triazenes have many applications and properties. [2][3][4] Derivatives of these compounds can be used as various drugs like anti-cancers. [5] However, many derivatives of these compounds are used in paint industry as color indicators.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, vibrational, electrostatic potential and NMR studies of (E and Z) 1-(4-chloro-3-nitrophenyl)-3-(2-methoxyphenyl)triazene: Combined experimental and DFT approaches

Rofouei¹,

Soleymani

Aghaei³

et al. 2016

Journal of Molecular Structure

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Highly Efficient Brønsted Acidic Ionic Liquid Promoted Direct Diazenylation of Pyrazolones with Aryltriazenes under Mild Conditions

Zhang

Liu

et al. 2016

Asian J Org Chem

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We report the first Brønsted acidic ionic liquid (IL) promoted reactiono f5 -pyrazolones with aryltriazenes to prepare arylazopyrazolones. The reaction was carried out with the aryltriazenes as diazotizing agents, water as the solvent, and the ionic liquid as the promoter at room tempera-ture under air and metal-free conditions. The desired products were obtainedi ng ood to excellent yields. Notably, ag ram-scale experiment and al ate-stage diazenylationr eaction of ap harmaceutical derivative alsof urnished the desired products under mild conditions.

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Novel One-Pot Synthesis of Thiophenols from Related Triazenes under Mild Conditions

Cited by 20 publications

References 24 publications

Bond analysis in meta- and para-substituted thiophenols: overlap descriptors, local mode analysis, and QTAIM

Bond analysis in meta- and para-substituted thiophenols: overlap descriptors, local mode analysis, and QTAIM

Synthesis, vibrational, electrostatic potential and NMR studies of (E and Z) 1-(4-chloro-3-nitrophenyl)-3-(2-methoxyphenyl)triazene: Combined experimental and DFT approaches

Highly Efficient Brønsted Acidic Ionic Liquid Promoted Direct Diazenylation of Pyrazolones with Aryltriazenes under Mild Conditions

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