Facile synthesis of highly substituted 2-pyrone derivatives via a tandem Knoevenagel condensation/lactonization reaction of β-formyl-esters and 1,3-cyclohexadiones

Moghaddam, Firouz Matloubi; Mirjafary, Zohreh; Javan, Marjan Jebeli; Motamen, Sara; Saeidian, Hamid

doi:10.1016/j.tetlet.2014.02.104

Cited by 18 publications

(4 citation statements)

References 33 publications

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“…Knoevenagel condensation is a productive reaction for the formation of CC bonds having various applications in the synthesis of pharmaceuticals (metallothionein-3 (MT3) ligand, 2-pyrone derivatives) and fine chemicals. − Knoevenagel condensation is a strategic step in the industrial scale manufacture of antimalarial drug lumifantrine (a constituent of coartem). , The reaction has a wide range of applications regarding coumarin and its derivatives’ synthesis that is a significant moiety of organic compounds and is also employed as additives in both cosmetics and the food industry . Knoevenagel condensation has been employed in the total synthesis of a multitargeted kinase inhibitor .…”

Section: Introductionmentioning

confidence: 99%

Amide Functionalized Mesoporous MOF LOCOM-1 as a Stable Highly Active Basic Catalyst for Knoevenagel Condensation Reaction

et al. 2023

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Acyl-amide is extensively used as functional group and is a superior contender for the design of MOFs with the guest accessible functional organic sites. A novel acyl-amide-containing tetracarboxylate ligand, bis(3,5-dicarboxy-pheny1)terephthalamide, has been successfully synthesized. The H4L linker has some fascinating attributes as follows: (i) four carboxylate moieties as the coordination sites confirm affluent coordination approaches to figure a diversity of structure; (ii) two acyl-amide groups as the guest interaction sites can engender guest molecules integrated into the MOF networks through H-bonding interfaces and have a possibility to act as functional organic sites for the condensation reaction. A mesoporous MOF ([Cu2(L)(H2O)3]·4DMF·6H2O) has been prepared in order to produce the amide FOS within the MOF, which will work as guest accessible sites. The prepared MOF was characterized by CHN analysis, PXRD, FTIR spectroscopy, and SEM analysis. The MOF showed superior catalytic activity for Knoevenagel condensation. The catalytic system endures a broad variety of the functional groups and presents high to modest yields of aldehydes containing electron withdrawing groups (4-chloro, 4-fluoro, 4-nitro), offering a yield > 98 in less reaction time as compared to aldehydes with electron donationg groups (4-methyl). The amide decorated MOF (LOCOM-1-) as a heterogeneous catalyst can be simply recovered by centrifugation and recycled again without a flagrant loss of its catalytic efficiency.

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Section: Introductionmentioning

confidence: 99%

Amide Functionalized Mesoporous MOF LOCOM-1 as a Stable Highly Active Basic Catalyst for Knoevenagel Condensation Reaction

et al. 2023

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“…The Knoevenagel condensation reaction, in which an activated methylene group joins with the carbonyl carbon of a ketones or aldehyde, is an important reaction for the industrial-scale formation of C-C bonds and is often employed for the synthesis of functional polymers, ne chemicals, cosmetics, and pharmaceuticals [18][19][20][21]. This reaction is typically conducted using homogeneous bases as catalysts, such as amines, alkali metal hydroxides and ammonium salts [22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Enhanced Catalysis of Mechano-Chemically Synthesized KMgF3 Catalysts for the Knoevenagel Condensation

Iida,

Sugiyama,

Horie

2023

Catal Surv Asia

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Catalysis of KMgF 3 catalysts for Knoevenagel condensation were enhanced by synthesizing mechanochemically. The BET surface area and number of strongly basic site of KMgF 3 were increased by applying greater mechanical energy (higher rotation rate) in a mechano-chemical process. Their increases were caused by stronger mechano-chemical effects such as the micronization of the particles and the creation of lattice defect on the surface, resulted in resulted in the enhancement of catalytic activity of KMgF 3 for Knoevenagel condensation. The XPS analysis revealed that the element composition on the surface of KMgF 3 was similar with K 2 MgF 4 and indicated the possibility which the true active component for this reaction was K 2 MgF 4 rather than KMgF 3 . The kinetic measurements revealed that the Knoevenagel condensation catalyzed by KMgF 3 was regard as a rst order reaction and apparent activation energy was estimated at 55.8 kJmol -1 . A soluble component capable of acting as a catalyst was not present in the solution and the KMgF 3 acted as a true solid catalyst.

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“…Given the presence of numerous amine groups, we decided to employ the newly obtained amine cross‐linked polymers as catalysts for the Knoevenagel condensation reaction. Knoevenagel condensation reaction is widely employed in the synthesis of electron‐poor olefins and a wide range of pharmaceuticals and fine chemicals . Moreover, the current intense interest aroused by this kind of reaction is also witnessed by the extensive research efforts regarding the development of different heterogeneous catalysts for the Knoevenagel condensation as alternative to homogeneous catalysis.…”

Section: Introductionmentioning

confidence: 99%

Cross‐Linked Polyamine from Imidazolium‐Based Materials: A Simple Route to Useful Catalytic Materials

et al. 2018

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Cross‐linked polyamine‐based materials were easily prepared by reduction of the corresponding cross‐linked imidazolium‐based materials with sodium borohydride in hot ethanol. Overall, the synthetic procedure is based on the polymerization of a suitable bis‐vinylimidazolium salt with or without a suitable support, such as silica or silica‐coated magnetic nanoparticles (γ‐Fe2O3@SiO2), followed by reduction. This simple approach allows the synthesis of materials based on a network of secondary and tertiary amines. Materials were characterized by 13C cross‐polarization magic angle spinning NMR (13C CPMAS NMR), proton spin‐lattice relaxation times in the rotating frame (T1ρH) and thermogravimetric analysis (TGA). Cross‐linked polyamine‐based materials were used as recoverable catalyst for Knoevenagel reaction. High yields of the condensation products were obtained and up to 11 cycles were carried out.

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Facile synthesis of highly substituted 2-pyrone derivatives via a tandem Knoevenagel condensation/lactonization reaction of β-formyl-esters and 1,3-cyclohexadiones

Cited by 18 publications

References 33 publications

Amide Functionalized Mesoporous MOF LOCOM-1 as a Stable Highly Active Basic Catalyst for Knoevenagel Condensation Reaction

Amide Functionalized Mesoporous MOF LOCOM-1 as a Stable Highly Active Basic Catalyst for Knoevenagel Condensation Reaction

Enhanced Catalysis of Mechano-Chemically Synthesized KMgF3 Catalysts for the Knoevenagel Condensation

Cross‐Linked Polyamine from Imidazolium‐Based Materials: A Simple Route to Useful Catalytic Materials

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