Rapid Sequentially Palladium Catalyzed Four-Component Synthesis of Novel Fluorescent Biaryl-Substituted Isoxazoles

Deden, Tobias; May, Lars; Reiß, Guido J.; Müller, Thomas J. J.

doi:10.3390/catal10121412

Cited by 5 publications

(8 citation statements)

References 51 publications

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“…In one‐pot preparation of 3‐biaryl‐substituted isoxazoles 3 , a Pd‐catalyzed Sonogashira coupling of an aroyl chloride 1 with p‐bromophenyl acetylene 2 was conducted [48]. Later on the product that is, corresponding alkynone, the successive cyclo‐condensation reaction was done with hydroxylamine very fastly by using the microwave which was followed by Suzuki coupling of various boronic acids, without further addition of Pd catalysts to the reaction mixture (Scheme 27).…”

Section: Synthetic Methods Of Isoxazole and Their Derivativesmentioning

confidence: 99%

“…solvents such as acetonitrile, EtOH, THF, Toluene, water, and DMF, but the solvent-free reaction condition was found to form more yield (> 95%) than the solvent condition (25%-70%). The plausible mechanism has been proposed as follows: The first step is the Lewis-acid sites S C H E M E 2 5 Synthetic pathway of the trifluoromethylated flavonoid isoxazoles under microwave radiation [46] S C H E M E 2 6 Preparation of (E)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one using microwave technology [47] S C H E M E 2 7 One-pot preparation of 3-biaryl-substituted isoxazoles using a Pdcatalyzed Sonogashira coupling reaction [48] (Al +3 ) of ZSM-5 activate carbonyl oxygen of ethyl acetoacetate 3. Oximation of activated ethyl acetoacetate produces intermediate 5 which can undergo Knoevenagel condensation with an activated aldehyde 1 leads the formation of intermediate 6.…”

Section: Other Synthetic Routesmentioning

confidence: 99%

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A review of recent synthetic strategies and biological activities of isoxazole

Pandhurnekar¹,

Pandhurnekar

Mungole³

et al. 2022

Journal of Heterocyclic Chem

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Among different heterocyclic compounds, isoxazole and their analogues are very important classes of heterocyclic compounds as they display an extensive range of biological actions. This makes such scaffolds very important structures in the field of medicinal chemistry. From an extensive literature assessment, isoxazole is clinically proven to be very effective as an anti‐bacterial, anti‐fungal, anti‐inflammatory, anti‐cancer, anti‐tubercular, and anti‐neoplastic agent. The different derivatives of isoxazole which exhibits adjustment in their structure have shown a high degree of variety in their medicinal properties which makes evident them as very beneficial in the progress of novel bioactive drugs which show enhanced effectiveness along with minor harmfulness. Structural aspects of isoxazole having aromaticity with weaker nitrogen‐oxygen bonding provide a potential site for the ring cleavage. Thus, this isoxazole ring system allows easier modifications of substituents in their ring structure which consequently make isoxazole very useful intermediates in various synthetic routes of bioactive compounds. Hence, the synthesis and evaluation of isoxazole‐containing molecules with wider therapeutic consequences are always the topic of interest for chemists. Hence, in light of this comprehensive research on isoxazole, it is thought worthwhile to review various pathways for the synthesis of isoxazole analogues and having a broad spectrum of bioactive actions.

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Section: Synthetic Methods Of Isoxazole and Their Derivativesmentioning

confidence: 99%

Section: Other Synthetic Routesmentioning

confidence: 99%

A review of recent synthetic strategies and biological activities of isoxazole

Pandhurnekar¹,

Pandhurnekar

Mungole³

et al. 2022

Journal of Heterocyclic Chem

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“…In addition, 19 examples of 1,3,5-substituted pyrazoles were obtained in 75-92% yield by adding (phenyl)hydrazine to the in situ generated ynones underlining the versatility of the one-pot sequence. Similarly, Deden and coauthors showed that this cyclocondensation route was readily elaborated to a sequentially Pd-catalyzed four-component synthesis of intensively fluorescent biaryl-substituted isoxazoles with donor-acceptor decoration in moderate-to-good yields [93].…”

Section: Scheme 27mentioning

confidence: 98%

Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Niedballa

Müller

2022

Catalysts

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Multicomponent processes are beneficial tools for the synthesis of heterocycles. As densely substituted bifunctional electrophiles, ynones are essential intermediates by applying cyclocondensations or cycloadditions in numerous heterocycle syntheses. The respective alkynoyl intermediates are generally accessible by palladium-, copper- and palladium/copper-catalyzed alkynylation. In turn, the mild reaction conditions allow for a fast and versatile entry to functional heterocycles in the sense of consecutive multicomponent processes. This review collates and presents recent advances in accessing thirteen heterocycle classes and their applications by virtue of catalytic alkynoyl generation in diversity-oriented multicomponent syntheses in a one-pot fashion.

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“… 17 The sonication method is also regarded as a one-pot multicomponent reaction method, which is recently discovered for the synthesis of heterocyclic compounds. 18 − 21 …”

Section: Introductionmentioning

confidence: 99%

“…Ultrasound irradiation-based chemical reactions have great importance in chemistry due to mild reaction conditions, with good yield, improved selectivity, and in short time in comparison to the conventional methods . The sonication method is also regarded as a one-pot multicomponent reaction method, which is recently discovered for the synthesis of heterocyclic compounds. − …”

Section: Introductionmentioning

confidence: 99%

Isoxazole Derivatives against Carbonic Anhydrase: Synthesis, Molecular Docking, MD Simulations, and Free Energy Calculations Coupled with In Vitro Studies

et al. 2022

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Heterocyclic compounds with a five-membered ring as a core, particularly those containing more than one heteroatom, have a wide spectrum of biological functions, especially in enzyme inhibition. In this study, we present the synthesis of five-membered heterocyclic isoxazole derivatives via sonication of ethyl butyrylacetate with aromatic aldehyde in the presence of a SnII-Mont K10 catalyst. The synthesized compounds were characterized using sophisticated spectroscopic methods. In vitro testing of the compounds reveals three derivatives with significant inhibitory action against carbonic anhydrase (CA) enzyme. The compound AC2 revealed the most promising inhibitory activity against CA among the entire series, with an IC 50 = 112.3 ± 1.6 μM (% inh = 79.5) followed by AC3 with an IC 50 = 228.4 ± 2.3 μM (% inh = 68.7) compared to the standard with 18.6 ± 0.5 μM (% inh = 87.0). Molecular docking (MD) study coupled with extensive MD simulations (400 ns) and MMPBSA study fully supported the in vitro enzyme inhibition results, evident from the computed Δ G bind (AC2 = −13.53 and AC3 = −12.49 kcal/mol). The in vitro and in silico studies are also augmented by a fluorescence-based enzymatic assay in which compounds AC2 and AC3 showed significant fluorescence enhancement. Therefore, on the basis of the present study, it is inferred that AC2 and AC3 may serve as a new framework for designing effective CA inhibitors.

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Rapid Sequentially Palladium Catalyzed Four-Component Synthesis of Novel Fluorescent Biaryl-Substituted Isoxazoles

Cited by 5 publications

References 51 publications

A review of recent synthetic strategies and biological activities of isoxazole

A review of recent synthetic strategies and biological activities of isoxazole

Heterocycles by Consecutive Multicomponent Syntheses via Catalytically Generated Alkynoyl Intermediates

Isoxazole Derivatives against Carbonic Anhydrase: Synthesis, Molecular Docking, MD Simulations, and Free Energy Calculations Coupled with In Vitro Studies

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