Synthesis of 5-Acyl-3,4-dihydropyrimidine-2-thiones via Solvent-Free, Solution-Phase and Solid-Phase Biginelli Procedures

Comas, Horacio; Buisson, David‐Alexandre; Najman, Romain; Kozielski, Frank; Rousseau, Bernard; Lopez, Roman

doi:10.1055/s-0029-1217373

Cited by 4 publications

(1 citation statement)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The heterocyclic Biginelli scaffold has also been obtained under various synthesis conditions such as water or ionic liquids as solvent. Alternatively, this reaction was conducted either under solvent–free conditions or under microwave irradiation . Among various activated catalysts, Baker's yeast, iodine, Zeolite, ion exchange resin, ethyl polyphosphate, TMSCl, TMSCl–NaI, and FeCl 3 –Si(OEt)4 have been used in this procedure.…”

Section: Introductionmentioning

confidence: 99%

Immobilized Gelatin–λ–Carrageenan on Magnetite Nanoparticles as an Efficient Organocatalyst for Enantioselective Biginelli Reaction

Jafari-Chermahini

Tavakol

2019

ChemistrySelect

View full text Add to dashboard Cite

A facile method for preparation of stabilized and functionalized nanoparticles (NPs) from magnetite by successive application of blended natural polymers (gelatin and λ–carrageenan) on Fe3O4 core has been developed. Gelatin plays a privileged role in the catalytic active sites and it is responsible for the enantiomeric induction. λ–carrageenan endowed chemical stability for immobilization of gelatin on Fe3O4 nanoparticles, thereby enhancing its stability and recoverability. The versatility of the modified NPs was proved by their excellent heterogeneous catalytic activity in one–pot, three–component Biginelli cyclocondensation reaction involving an aromatic aldehyde, urea, and ethyl acetoacetate (or Dimedone) to afford optically active corresponding dihydropyrimidinones in acceptable yields. This novel and green protocol has several advantages such as high efficiency, reusability of the catalyst, using inexpensive and available compounds for the catalyst.

show abstract

Section: Introductionmentioning

confidence: 99%

Immobilized Gelatin–λ–Carrageenan on Magnetite Nanoparticles as an Efficient Organocatalyst for Enantioselective Biginelli Reaction

Jafari-Chermahini

Tavakol

2019

ChemistrySelect

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: Synthesis of 5‐Acyl‐3,4‐dihydropyrimidine‐2‐thiones via Solvent‐Free, Solution‐Phase and Solid‐Phase Biginelli Procedures.

Comas¹,

Buisson²,

Najman³

et al. 2009

ChemInform

View full text Add to dashboard Cite

Procedures. -The title compounds (IV) are synthesized using a solvent-free solution phase Biginelli condensation reaction. An analogous protocol involving polymer-supported m-hydroxybenzaldehyde gives only low yields (10-15%) of dihydropyrimidine-2-thiones. -(COMAS, H.; BUISSON, D.-A.; NAJMAN, R.; KOZIELSKI, F.; ROUSSEAU, B.; LOPEZ*, R.; Synlett 2009, 11, 1737-1740; Commis. Energ. At., Dep. Bioorg. Chem., CEA, F-91191 Gif-sur-Yvette, Fr.; Eng.) -Mais 49-166

show abstract

Solid Heterogeneous Catalysts Based on Sulfuric Acid and Transition-Metal Salts: Synthesis of Bioactive Heterocycles

Karami¹

2014

Heterogeneous Catalysis

View full text Add to dashboard Cite

Synthesis of 5-Acyl-3,4-dihydropyrimidine-2-thiones via Solvent-Free, Solution-Phase and Solid-Phase Biginelli Procedures

Cited by 4 publications

References 2 publications

Immobilized Gelatin–λ–Carrageenan on Magnetite Nanoparticles as an Efficient Organocatalyst for Enantioselective Biginelli Reaction

Immobilized Gelatin–λ–Carrageenan on Magnetite Nanoparticles as an Efficient Organocatalyst for Enantioselective Biginelli Reaction

ChemInform Abstract: Synthesis of 5‐Acyl‐3,4‐dihydropyrimidine‐2‐thiones via Solvent‐Free, Solution‐Phase and Solid‐Phase Biginelli Procedures.

Solid Heterogeneous Catalysts Based on Sulfuric Acid and Transition-Metal Salts: Synthesis of Bioactive Heterocycles

Contact Info

Product

Resources

About