The First Solvent‐Free, Microwave‐Accelerated, Three‐Component Synthesis of Thiazolidin‐4‐ones via One‐Pot Tandem Staudinger/aza‐Wittig Reaction

Shanmugavelan, Poovan; Sathishkumar, Murugan; Nagarajan, Sangaraiah; Raja, R.; Ponnuswamy, Alagusundaram

doi:10.1002/jhet.1705

Cited by 13 publications

(3 citation statements)

References 45 publications

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“…9-anthraldehyde. 21,24,25 Microwave irradiation can also be applied to accelerate reaction rates provided phosphorane 23,26 or phosphazene 27 stability. In dry conditions, the Wittig reaction has also been shown to occur in the presence of alumina or potassium fluoride supported on alumina, which after stirring for 48 hours afforded the alkene products in a E:Z ratio 92:8 to 1:1.…”

Section: Resultsmentioning

confidence: 99%

Borylated methyl cinnamates: Expedited synthesis, characterization, crystallographic analysis and biological activities in glycosidase inhibition and in cancer cells lines.

Legge¹,

Shimadate²,

Ghorbani³

et al. 2021

Preprint

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Three cinnamate derivatives bearing a boronate pinacol ester group para, meta and ortho to the a,b-unsaturated ester group have been synthesized via a solventless, expedited Wittig protocol in the best stereoisomeric ratios yet reported, purified by recrystallization, characterized and analyzed by X-ray crystallography. These are valuable building blocks to biologically active derivatives and are themselves biologically active drug leads, displaying excellent selectivities as glycosidase modulators and for future testing as boron neutron capture therapy (BNCT) agents. In a panel of 15 glycosidases, IC50 values of 351 mM and 374 mM were shown for para 2 against almond b-glucosidase and bovine liver b-galactosidase, respectively. For meta 2 the selectivity profile is improved with only inhibition of bovine liver b-galactosidase with an IC50 of 780 mM. These borylated derivatives also possess the capability to be used as BNCT agents. This occurs via irradiation with slow neutrons, thus granting them a switch-on/switch-off toxicity. This is an important new capability imbued into anticancer drugs, too many of which are too toxic in their therapeutic window. BNCT drugs bearing the organic boron pharmacophore have the potential to fine-tune the timing of toxicity delivery.

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Section: Resultsmentioning

confidence: 99%

Borylated methyl cinnamates: Expedited synthesis, characterization, crystallographic analysis and biological activities in glycosidase inhibition and in cancer cells lines.

Legge¹,

Shimadate²,

Ghorbani³

et al. 2021

Preprint

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show abstract

“…In view of the above and as part of our ongoing research platform on the eco‐friendly syntheses of biologically important heterocyclic/hybrid heterocyclic compounds under solvent‐free, and aqueous conditions, herein, we report a smart and efficient green synthesis of novel 1, 2, 3‐triazolyl pyrazoline‐/indazolyl‐carbothioamide hybrids from the sequential reactions of ketones, aldehydes, hydrazine hydrate and aryl isothiocyanates under one‐pot, solvent‐free grinding strategy at room temperature.…”

Section: Introductionmentioning

confidence: 99%

A Smart and Efficient One‐Pot Green Synthesis of Novel 1, 2, 3‐Triazolyl Pyrazoline‐/Indazolyl‐Carbothioamide Hybrids under Solvent‐Free Grinding Strategy at Room Temperature

et al. 2018

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A smart and straightforward route has been developed for the green synthesis of novel 1,2,3-triazolyl pyrazoline-/indazolylcarbothioamide hybrids from easily accessible starting materials for the first time via one-pot sequential four component reaction under solvent-free grinding protocol at room temper-ature. Notably, this protocol is meritorious in the sense that it is inexpensive, expeditious, devoid of tedious separation methods, environmentally benign and it involves mild reaction conditions affording good to excellent yields (84-97%) of the products.

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“…Several synthetic strategies have been reported for the synthesis of five‐, six‐, and seven‐membered heterocyclic compounds. The reactions investigated in the current study are shown in Schemes 2– . These compounds can be prepared using a variety of different reactants based on protocols reported in the literature (Schemes 2–) …”

Section: Introductionmentioning

confidence: 99%

Sustainable Catalytic Process with a High Eco‐Scale Score for the Synthesis of Five‐, Six‐, and Seven‐Membered Heterocyclic Compounds Using Nanocrystalline Zeolites

Sarmah

Srivastava

2017

Asian J Org Chem

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Nanocrystalline ZSM-5 and Beta zeolites were evaluated as catalysts for the one-pot synthesis of aw ide range of five-, six-, and seven-memberedh eterocyclic compounds. Seven-membered compounds were prepared by the reaction of o-phenylenediamine and ketones, whereas five-membered compounds were obtained when o-aminothiophenol was reactedw ith ketones under the same reactionc ondition. Severalo ther seven-membered compounds werep repared by the reaction of (E)-chalcone with o-phenylenediamine/o-aminothiophenol, whereas the six-membered compounds described in this study were prepared by the reaction of o-phenylenediamine with 2-bromoacetophenone/2hydroxy acetophenone. Twoo ther five-membered compounds were prepared by the reactiono fa niline with ben-zaldehyde and thioglycolic acid, and the reaction of glycerol with acetone. The mechanisms responsible for the formation of the different products were elucidated based on the results of time-dependent 1 HNMR experiments.T ot he best of our knowledge, this work represents the first reported systematicassessment of the catalytic activity of nanocrystalline zeolites for the synthesis of heterocyclic compounds. Notably,t he catalysts were readily recovered and reused without any considerable decrease in their catalytic activity.T he high eco-scale score and low E-factorv alue of this process clearly demonstrate that it represents ag reen and sustainable synthetic route for the preparation of aw ide range of heterocyclic compoundso fs ignificant industrial importance.Scheme1.Some representative examples of biologically important molecules containingf ive-, six-, and seven-membered heterocyclicunits.Scheme2.Various pathways for the construction of five-membered heterocyclic compoundsreported in the literature.

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The First Solvent‐Free, Microwave‐Accelerated, Three‐Component Synthesis of Thiazolidin‐4‐ones via One‐Pot Tandem Staudinger/aza‐Wittig Reaction

Cited by 13 publications

References 45 publications

Borylated methyl cinnamates: Expedited synthesis, characterization, crystallographic analysis and biological activities in glycosidase inhibition and in cancer cells lines.

Borylated methyl cinnamates: Expedited synthesis, characterization, crystallographic analysis and biological activities in glycosidase inhibition and in cancer cells lines.

A Smart and Efficient One‐Pot Green Synthesis of Novel 1, 2, 3‐Triazolyl Pyrazoline‐/Indazolyl‐Carbothioamide Hybrids under Solvent‐Free Grinding Strategy at Room Temperature

Sustainable Catalytic Process with a High Eco‐Scale Score for the Synthesis of Five‐, Six‐, and Seven‐Membered Heterocyclic Compounds Using Nanocrystalline Zeolites

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