Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Ракитин, Олег А.

doi:10.3390/molecules26123595

Cited by 18 publications

(11 citation statements)

References 126 publications

(185 reference statements)

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“…The synthesis of DTTs is easy and provides the reaction of anethole with elemental sulfur; these compounds can also be easily added to other molecules to obtain drug–DTT conjugates. Nevertheless, different synthetic methods have been proposed for their preparation [ 163 ]. The most used synthetic strategy is based on the dehydrogenation and sulfurization of an allylic methyl group ( a ) which involves treatment with elemental sulfur or phosphorus pentasulfide ( Figure 10 ).…”

Section: H 2 S Donors and Diseasesmentioning

confidence: 99%

H2S Donors and Their Use in Medicinal Chemistry

Magli¹,

Perissutti²,

Santagada³

et al. 2021

Biomolecules

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Hydrogen sulfide (H2S) is a ubiquitous gaseous signaling molecule that has an important role in many physiological and pathological processes in mammalian tissues, with the same importance as two others endogenous gasotransmitters such as NO (nitric oxide) and CO (carbon monoxide). Endogenous H2S is involved in a broad gamut of processes in mammalian tissues including inflammation, vascular tone, hypertension, gastric mucosal integrity, neuromodulation, and defense mechanisms against viral infections as well as SARS-CoV-2 infection. These results suggest that the modulation of H2S levels has a potential therapeutic value. Consequently, synthetic H2S-releasing agents represent not only important research tools, but also potent therapeutic agents. This review has been designed in order to summarize the currently available H2S donors; furthermore, herein we discuss their preparation, the H2S-releasing mechanisms, and their -biological applications.

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Section: H 2 S Donors and Diseasesmentioning

confidence: 99%

H2S Donors and Their Use in Medicinal Chemistry

Magli¹,

Perissutti²,

Santagada³

et al. 2021

Biomolecules

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“…It has to be stressed that the fluoride anion-mediated sulfurization of 2,3-diarylcyclopropenthiones 37 should be considered as a useful method for the synthesis of 1,2-dithiole-3-thiones of type 38 . The latter sulfur heterocycles are of importance as biologically active compounds, and in a recent review, the method of their synthesis as well as diverse transformations have been summarized [ 38 ].…”

Section: Five-membered S-heterocyclesmentioning

confidence: 99%

Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions

2022

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Fluorinated heterocycles constitute an important group of organic compounds with a rapidly growing number of applications in such areas as medicinal chemistry, agrochemicals production, polymer chemistry, as well as chemistry of advanced materials. In the latter case, fluorinated thiophenes are considered as a lead class of compounds with numerous spectacular applications. On the other hand, cycloaddition reactions offer a superior methodology for stereo-chemically controlled synthesis of heterocycles with a diverse ring size and a variable number of heteroatoms. A comprehensive review of methods based on cycloaddition reactions and applied for construction of fluorinated and/or fluoroalkylated S-heterocycles has not yet been published. For this reason, the main goal of the presented review was to fill the existing gap and to summarize the results published over last six decades. In this context, the [3+2]- and [4+2]-cycloadditions (Huisgen reactions, and Diels–Alder reactions, respectively) are of special importance. Some questions related to the discussed mechanisms of cycloaddition processes observed in reactions with electron deficient, fluorinated substrates (dipolarophiles and dienophiles), and electron-rich sulfur containing counter partners, are of fundamental importance for the development of interpretations of organic reaction mechanisms.

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“…As a consequence, the chemistry of this class of compounds remains a subject of active research. So far, these heterocycles, in particular 1,2-dithiole-3-thiones types, as a class of organosulfur compounds, have been intensively studied and used as scaffolds in a variety of synthetic transformations . Conversely, 3-acylimino-1,2-dithiole derivatives − , remained underexplored and further development is much needed to widen the access to this class of compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Being a class of most intensively studied biologically important 1,2-dithiols, this preliminary experimental result strongly motivated us to investigate this ionic liquid-mediated addition of thiocarboxylic acids to alkynylnitriles to produce 3-acylimino-3 H -1,2-dithiol derivatives in detail. Although a literature survey shows the imprints of the synthesis of 3-acylimino-1,2-dithiole derivatives in the early 1960s from 3H -1,2-dithiol-3-thiones, however, these multistep protocols involving relatively lengthy procedures suffer from harsh reaction conditions and low yields (Scheme a,b) …”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid-Mediated One-Pot 3-Acylimino-3H-1,2-dithiole Synthesis from Thiocarboxylic Acids and Alkynylnitriles via In Situ Generation of Disulfide Intermediates

Kumari

Goswami

2022

J. Org. Chem.

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A practical and straightforward strategy for the synthesis of 3-acylimino-3H-1,2-dithiol derivatives via a metal-free annulation reaction of alkynylnitriles with thiocarboxylic acids mediated by ionic liquids [BMIM]Br has been reported. This operationally simple protocol offers an easy and rapid access to a library of dithiol derivatives in moderate to good yields. The mechanistic studies show a benzoyldithio anion addition to alkynylnitriles followed by an annulation reaction through the involvement of a disulfide moiety as the key intermediate.

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Synthesis and Reactivity of 3H-1,2-dithiole-3-thiones

Cited by 18 publications

References 126 publications

H2S Donors and Their Use in Medicinal Chemistry

H2S Donors and Their Use in Medicinal Chemistry

Synthesis of Fluorinated and Fluoroalkylated Heterocycles Containing at Least One Sulfur Atom via Cycloaddition Reactions

Ionic Liquid-Mediated One-Pot 3-Acylimino-3H-1,2-dithiole Synthesis from Thiocarboxylic Acids and Alkynylnitriles via In Situ Generation of Disulfide Intermediates

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