Ultrasound Promoted One Pot Synthesis of 1,5-Benzothiazepines Using Polyethylene Glycol (Peg-400)

Devkate, Chandrashekhar G.; Kola, S.; Gaikwad, Digambar D.; Siddique, Mohammad Idrees M

doi:10.7897/2230-8407.0911280

Cited by 9 publications

(3 citation statements)

References 10 publications

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“…Early works have been reviewed in 2005. , Since then, much progress has been made. Especially, one-pot synthesis type reactions, where many different components react in one step, have been successfully carried out in PEG due to its ability to dissolve a wide range of compounds. − In fact, PEG can also dissolve mineral salts, , a contributing factor for its successful use as the reaction medium for the synthesis of metal–organic frameworks . Pd-catalyzed reactions (the importance of these can be seen in the 2010 Nobel prize award for their discovery) have also been carried out in PEG under both homocatalytic and heterocatalytic conditions where Pd is immobilized onto a porous silica material. − PEGs have also been successfully used as components in deep eutectic solvents. − Despite all of these successes, there are only limited experimental and theoretical studies on the dynamics of neat PEG. − Experimental physicochemical properties of PEGs are needed to further this effort.…”

Section: Introductionmentioning

confidence: 99%

Densities, Viscosities, and Self-Diffusion Coefficients of Ethylene Glycol Oligomers

Hoffmann

Horowitz

Gutmann³

et al. 2021

J. Chem. Eng. Data

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Polyethylene glycol (PEG) is gaining interest as an alternative green solvent in chemical synthesis and processing. This report presents density and viscosity data from 293.15 K to 358.15 K as well as self-diffusion coefficient data from 298.15 K to 358.15 K for oligomers of PEG from di-to nonaethylene glycol. The results were obtained by extrapolation from measurement series where water, the most common impurity in PEGs, was intentionally added in several increments. The obtained results are carefully compared to literature data, which are widely available only for density and viscosity, and only for the lower oligomers. Densities are found to be linearly dependent on temperatures for all studied oligomers. The temperature dependence of viscosity and self-diffusion coefficients show only slight deviations from the Arrhenius equation over the investigated temperature range. The activation energies obtained from the viscosity data agree well with the activation energies from the self-diffusion coefficient data and appear to be linearly dependent with respect to the number of ethylene oxide repeat units in the PEG oligomer. This linearity combined with the observation that the pre-exponential factor appears to be the same for all studied oligomers may serve as a tool to estimate viscosities and self-diffusion coefficients for higher oligomers within the investigated temperature range. The densities of the oligomers all fall within a rather narrow range without a clear trend in homologous series.

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Section: Introductionmentioning

confidence: 99%

Densities, Viscosities, and Self-Diffusion Coefficients of Ethylene Glycol Oligomers

Hoffmann

Horowitz

Gutmann³

et al. 2021

J. Chem. Eng. Data

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“…[19] One way to achieve this is by looking at alternative catalysts that can be re-used (e. g., Co 3 O 4 nanosheets [45] or H-Fer zeolites), [46] are non-toxic and cheaper (e. g., saturated ammonium chloride solution in water [10] or mango juice), [47] can be used in one-pot tandem reactions (e. g., nanocrystalline ZSM-5) [48] or either do not require the use of any solvent, or can be used with water as the solvent (e. g., tetra-n-butylammonium fluoride (TBAF) [49] or Na 2 CO 3 / tetrahexylammonium chloride (THAC) in water). [47] Another way to pursue greener approaches is to employ a different solvent that can be recycled and that allows for mild reaction conditions, such as hexafluoropropan-2-ol [50] and polyethylene glycol in combination with ultrasound irradiation, [51] or a biodegradable and non-toxic solvent, such as glycerol. [52] Lastly, ionic liquids can be considered as another green alternative as they can be re-used, can reduce the reaction time and can help to reduce the need of harmful catalysts.…”

Section: Synthesis Of 15-benzothiazepanes Through Reaction Of αβUnsat...mentioning

confidence: 99%

Synthesis of the 1,5‐Benzothiazepane Scaffold – Established Methods and New Developments

et al. 2023

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The 1,5‐benzothiazepane structure is an important heterocyclic moiety present in a variety of commercial drugs and pharmaceuticals. This privileged scaffold exhibits a diversity of biological activities, including antimicrobial, antibacterial, anti‐epileptic, anti‐HIV, antidepressant, antithrombotic and anticancer properties. Its important pharmacological potential renders research into the development of new and efficient synthetic methods of high relevance. In the first part of this review, an overview of different synthetic approaches toward 1,5‐benzothiazepane and its derivatives is provided, ranging from established protocols to recent (enantioselective) methods that promote sustainability. In the second part, several structural characteristics influencing biological activity are briefly explored, providing a few insights into the structure‐activity relationships of these compounds.

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“…Thanks to the success of the previous reaction, Kannan and co-workers extended the synthetic process to indole-based chalcones by reacting them with different carbohydrazides following the same ultrasonication conditions reported above ( Kannan et al, 2019 ). Finally, a one-pot cyclo condensation reaction was performed between chalcone derivatives and o -aminothiophenol by Devkate et al In their approach, several solvents were tested and PEG-400 was identified as the best choice providing a shorter reaction time and straightforward separation procedures for the target 1,5-benzothiazepines ( Devkate et al, 2018 ).…”

Section: 1 Ultrasound Chemistrymentioning

confidence: 99%

The green chemistry of chalcones: Valuable sources of privileged core structures for drug discovery

Marotta

Rossi²,

Ibba³

et al. 2022

Front. Chem.

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The sustainable use of resources is essential in all production areas, including pharmaceuticals. However, the aspect of sustainability needs to be taken into consideration not only in the production phase, but during the whole medicinal chemistry drug discovery trajectory. The continuous progress in the fields of green chemistry and the use of artificial intelligence are contributing to the speed and effectiveness of a more sustainable drug discovery pipeline. In this light, here we review the most recent sustainable and green synthetic approaches used for the preparation and derivatization of chalcones, an important class of privileged structures and building blocks used for the preparation of new biologically active compounds with a broad spectrum of potential therapeutic applications. The literature here reported has been retrieved from the SciFinder database using the term “chalcone” as a keyword and filtering the results applying the concept: “green chemistry”, and from the Reaxys database using the keywords “chalcone” and “green”. For both databases the time-frame was 2017–2022. References were manually selected based on relevance.

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Ultrasound Promoted One Pot Synthesis of 1,5-Benzothiazepines Using Polyethylene Glycol (Peg-400)

Cited by 9 publications

References 10 publications

Densities, Viscosities, and Self-Diffusion Coefficients of Ethylene Glycol Oligomers

Densities, Viscosities, and Self-Diffusion Coefficients of Ethylene Glycol Oligomers

Synthesis of the 1,5‐Benzothiazepane Scaffold – Established Methods and New Developments

The green chemistry of chalcones: Valuable sources of privileged core structures for drug discovery

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