Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

Bouasla, Souad; Amaro-Gahete, Juan; Esquivel, Dolores; López, María Isabel; Jiménez‐Sanchidrián, César; Teguiche, Mabrouk; Romero–Salguero, Francisco J.

doi:10.3390/molecules22122072

Cited by 38 publications

(17 citation statements)

References 41 publications

(38 reference statements)

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“…Therefore, the catalytic performance of Amberlyst-15 was compared with zeolite H-β and sulfonic acid functionalized hybrid material TS-OS-SO 3 H, performing the reaction under solvent-free conditions, at 130 • C for 20 min in a microwave reaction tube. Amberlyst-15 showed a higher catalytic activity (97% yield against 21-44% obtained with two others catalysts) due to its high density of acid centers [326]. It is also worth mentioning the work of Konrádová et al, who in 2017 developed an interesting protecting-group-free method starting from commercially available aromatic aldehydes and using a microwave promoted Wittig reaction of a stabilized ylide for the synthesis of different natural products, including coumarins.…”

Section: Microwave Assisted Reactionsmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

223

156

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Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

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Section: Microwave Assisted Reactionsmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

223

156

View full text Add to dashboard Cite

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“…Sulfated zirconia supported on silica (SiO 2 -SZ) and unsupported sulfated zirconia (SZ) have been used as acidic solid catalysts for measuring the catalytic activity of the esterification reaction between lauric acid and palmitic acid [48], while phosphated zirconia has been employed as a catalyst for the condensation reaction of phenols and ethyl acetoacetate to achieve coumarin derivatives [25]. Furthermore, microwave has been used to prepare coumarin derivatives in the presence of sulfated zirconia, commercial sulfonic acid resin or amberlite-15 [25,49]. Silica gel has also impregnated with sulfuric acid to work as acidic solid catalysts for isolating coumarin derivatives under a solvent free solution [50].…”

Section: Introductionmentioning

confidence: 99%

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

et al. 2018

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New modified acidic catalysts were prepared from the treatment of silica, titania and silica prepared from hydrolyzed tetraethyl orthosilicate (TEOS) with sulfuric and phosphoric acid. The sulfated and phosphated silica synthesized from TEOS were calcined at 450 and 650 • C. These catalysts were characterized by X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), transmission electron microscope (TEM), and scanning electron microscope (SEM). The surface areas, total pore volume, and mean pore radius of the acidic catalysts were investigated, while the pore size distribution was determined by the Barrett, Joyner and Halenda (BJH) method. The catalytic activity of the sulfated and phosphated silica and/or titania were examined with the Pechmann condensation reaction, in which different phenols reacted with ethyl acetoacetate as a neat reaction to obtain the corresponding coumarin derivatives. The results indicated that the treatment of the catalysts with sulfuric or phosphoric acid led to a decrease in the phases' crystallinity to a certain degree. The morphology and the structure of the acidified catalysts were examined and their particle size was calculated. Furthermore, the amount of the used catalysts played a vital role in controlling the formation of the products as well as their performance was manipulated by the number and nature of the active acidic sites on their surfaces. The obtained results suggested that the highest catalytic conversion of the reaction was attained at 20 wt % of the catalyst and no further increase in the product yield was detected when the amount of catalyst exceeded this value. Meanwhile the phenol molecules were a key feature in obtaining the final product.

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“…In summary, a series of new coumarin-triazole hybrids 8 (a-e) synthesized and characterized, and the crystal and molecular structure of the intermediate 3a was confirmed by crystallographic and computational studies. The compound 3a is stabilized through the formation of supramolecular ring motif [R 2 2 (14), R 2 2 (10) and R 2 1 (6)]. The HSA shows that, the intermolecular O…H (25.4%) interactions are the main contributor amongst the other interactions.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of coumarin-triazole hybrids: biocompatible anti-diabetic agents, in silico molecular docking and ADME screening

Basappa

Vivek²,

Kumara

et al. 2020

Heliyon

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The current study demonstrates the synthesis of coumarin-triazole hybrids 8 (a-e) in four steps starting from substituted salicylaldehyde 1 (a-e), and diethyl malonate 2. The spectroscopic studies provide the structure proofs of the new compounds, and the molecular structure of an intermediate 3a by crystallographic studies. The crystal structure analysis revealed the C-H...O, C-H... π, CO ...π and π...π molecular interactions. Further, the intermolecular interactions were quantified using Hirshfeld surface analysis and the DFT method B3LYP functional with 6-311þþ G (d,p) basis set was employed to optimize the molecular geometry. The synthesized new coumarintriazole hybrids, 8 (a-e) were screened for their α-amylase inhibitory potentials, and the results suggest that amongst the series, compounds 8c, and 8e show the promising inhibition of the enzyme, and might act as lead molecules for anti-diabetic activities. To understand the mode of action in silico molecular docking and ADME screening were performed.

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Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

Cited by 38 publications

References 41 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

Design and synthesis of coumarin-triazole hybrids: biocompatible anti-diabetic agents, in silico molecular docking and ADME screening

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