Convenient and Efficient Synthesis of Thiol Esters using Zinc Oxide as a Heterogeneous and Eco-Friendly Catalyst

Bandgar, B. P.; More, P. E.; Kamble, Vinod T.; Sawant, Sanjay S.

doi:10.1071/ch08202

Cited by 23 publications

(5 citation statements)

References 8 publications

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“…It is noted that Zn, ZnO, CoCl 2 , and BiCl 3 are active catalysts for the synthesis of some thiol esters with acetyl chloride at room temperature. A large number of experiments were carried out to screen an effective catalyst for the acylation of glutathione with acetyl chloride, and the results are presented in Table .…”

Section: Resultsmentioning

confidence: 99%

An Improved Process for Preparation of S-Acetyl-l-glutathione

Fang

Wang

Zhan

et al. 2015

Org. Process Res. Dev.

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An efficient one-step synthesis of S-acetyl-L-glutathione has been developed in a DMF−TFA mixed solvent with CoCl 2 as catalyst. This process not only has the advantages of selective acylation of the glutathione thiol group without involving the free amino but also highlights recycling of the relatively costly solvent TFA, which improves the yield to 91% and quality to 99.7%. The reaction is cost-effective, efficient, and easy to scale-up.

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Section: Resultsmentioning

confidence: 99%

An Improved Process for Preparation of S-Acetyl-l-glutathione

Fang

Wang

Zhan

et al. 2015

Org. Process Res. Dev.

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“…Under same conditions, in another reports, O-acylation of alcohols and phenols with acid chlorides were carried out using ZnO and nano ZnO. [51][52][53] Bromodimethylsulfonium bromide is an attractive reagent in organic synthesis. In the year of 2005, Khan and his co-workers utilized from this reagent for the acylation of alcohols, phenols, thiols and amines.…”

Section: Solvent-free Acylation Reactionsmentioning

confidence: 97%

Untitled

Kazemi

Sanchez-Mendoza

Ghobadi

2019

JMCS

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The hazardous and toxic nature of many solvents, in particular organic solvents that are extensively used in large scale for organic reactions have transformed a serious threat to the environment. Therefore, the design of solvent-free catalytic reaction has received considerable attention during recent times in the field of green synthesis. A solvent-free or solid state reaction may be accomplished using the reactants single or merge them in clays, zeolites, silica, alumina or other substrates. Esters, thioesters and amides are important and valuable compounds in the area of industry, medicine, pharmaceutical and heterocyclic chemistry. In this paper, various solventfree systems to synthesize esters, thioesters and amides via the acylation of alcohols, phenols, thiols and amines are described. In this review we summarized the activities presented mainly the recent years. reusable catalyst for the synthesis of esters and amides under solvent-free conditions (Scheme 5). 50 Scheme 3. Solvent-free diacylation of aldehydes using ATPB. Scheme 4. Solvent-free acylation of alcohols, thiols and amines catalyzed by ZrOCl 2 .8H 2 O.An convenient method with the same reagents and in the presence of lithium bis(perfluoroalkylsulfonyl)-imide (LiPFS-I) has also been developed (Scheme 24). 76 Scheme 24. Solvent-free acylation of alcohols using LiPFSI.Another practical and highly efficient strategy was also described with SiO 2 -Co(acac) 2 and SiO 2 -Cu(acac) 2 under solvent-free conditions (Scheme 25). 77 The acylation of alcohols, phenols and amines with acetyl chloride was carried out in less than 60 min at 50 0 C. The esterification of alcohols and amines was performed respectively with SiO 2 -Cu(acac) 2 and SiO 2 -Co(acac) 2. Scheme 25. Solvent-free acylation of alcohols and amines using SiO 2 -Co(acac) 2 and SiO 2 -Cu(acac) 2 . 7 M. Kazemi et al Journal of Medicinal and Chemical Sciences Review J. Med. Chem. Sci. 2019, 1, 1-8 http://jmchemsci.com Scheme 30. Solvent-free diacylation of aldehydes catalyzed by n-Sulfonic acid poly4-vinylpyridinum) hydrogen sulfate.

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“…2 In the Hantzsch condensation, it is reported that lesser reaction time and higher yield is more pronounced, with ZnO nanoparticles. 3 Thus, nano zinc oxide, being a more effective catalyst, is employed in new C-C, C-P, C-N, C-S bond formations via Michael addition reaction 4 , in synthesis of organic carbonates 5 , in Friedel-Crafts acylation [6][7][8] for the synthesis of aromatic ketones, in reaction of acid chlorides with alcohols /thiols / phenols 9 , Friedlander Quinolone synthesis 10, etc. Nano ZnO has also been employed under solvent-free conditions in reactions in which, a higher yield (90 -98 %) has been achieved.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterisation and Catalytic Studies of Nano Zinc Oxide-Alumina for Displacement Reaction on Carbonyldiimidazole

Sumathi¹,

Balaganesh²,

Balasubramanian³

2020

RJC

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Nano zinc oxide supported on alumina was prepared by chemical method and calcined at 300 o C. The calcined material was characterized by UV-Visible spectroscopy, Infra-Red spectroscopy, X-Ray Diffraction technique, Scanning Electron Microscopy, Thermogravimetric analysis and Porosimetry. The catalytic activity studies on alumina supported zinc oxide for the synthesis of disubstituted ureas through displacement reaction on carbonyldiimidazole are hitherto unreported. Thus, alumina supported nano zinc oxide was tested for its catalytic activity in the displacement reaction of carbonyldiimidazole with cyclohexylamine. While, the above reaction when carried out at room temperature, afforded 1,3-Dicyclohexyl urea, as the sole product in 88% yield in 20 hours, at 80 o C, 1,3-dicyclohexyl urea was obtained in 80% yield, in 4 hours. Reusable and safer catalysts, reaction at room temperature, simple workup and product with good yield and purity are the merits of this process.

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Convenient and Efficient Synthesis of Thiol Esters using Zinc Oxide as a Heterogeneous and Eco-Friendly Catalyst

Cited by 23 publications

References 8 publications

An Improved Process for Preparation of S-Acetyl-l-glutathione

An Improved Process for Preparation of S-Acetyl-l-glutathione

Untitled

Synthesis, Characterisation and Catalytic Studies of Nano Zinc Oxide-Alumina for Displacement Reaction on Carbonyldiimidazole

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