Polyoxometalate immobilized on MOF‐5 as an environment‐friendly catalyst for the synthesis of poly‐functionalized 3‐pyrrolin‐2‐ones

Li, Baole; Zhang, Hongyan; Di, Jia‐Qi; Zhang, Zhan‐Hui

doi:10.1002/aoc.6064

Cited by 5 publications

(5 citation statements)

References 86 publications

(41 reference statements)

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“…Immobilization of HPAs on suitable solid supports, such as metal oxides or silica-based materials is another common and effective strategy to solve the problem of difficult recovery of HPAs [84][85][86]. The loading of HPAs on suitable solid supports can overcome the issues of low specific surface and high solubility of HPAs; furthermore, supports can provide additional reaction sites.…”

Section: Hpas Supported On Suitable Solid Supportsmentioning

confidence: 99%

Polyoxometalate catalysts for the synthesis of N-heterocycles

Hu,

Li,

Chen

et al. 2024

Polyoxometalates

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N-Heterocycle compounds are crucial scaffolds in natural products, synthetic molecules, agricultural chemicals, and pharmaceuticals. Hence, green catalytic systems for the synthesis of N-heterocycles have been widely researched in organic synthesis and industrial catalysis. Polyoxometalates (POMs) are polynuclear metal-oxygen clusters with diverse structures and physicochemical properties. POMs exhibit multiple advantageous properties such as adjustable acidity, redox properties, high thermal stability, and nontoxic nature. Therefore, POMs have been widely investigated for their application in N-heterocycles synthesis and held great potential for industrial applications. In this review, we summarize recent advances (mainly from 2010 to 2023) in the synthesis of N-heterocycles, such as pyrroles, indoles, pyridines, and benzodiazepines, catalyzed by heteropolyacids (HPAs), modified HPA catalysts, and transition metal-modified POMs. The prospects of POM-based catalytic systems for the synthesis of N-heterocycles are also outlined.

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Section: Hpas Supported On Suitable Solid Supportsmentioning

confidence: 99%

Polyoxometalate catalysts for the synthesis of N-heterocycles

Hu,

Li,

Chen

et al. 2024

Polyoxometalates

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“…demonstrated the synthesis of poly‐functionalized 3‐pyrrolin‐2‐ones 19 in the presence of polyoxometalate immobilized on MOF‐5 through the one‐pot pseudo ‐four‐component reaction of dialkyl acetylenedicarboxylate 1 , amines 2 and aldehyde 6 in methanol at room temperature (Scheme 7). [16] …”

Section: Synthesis Of Five‐membered Rings With One Heteroatom Includingmentioning

confidence: 99%

“…[15] In 2020, Bao-Le et al demonstrated the synthesis of polyfunctionalized 3-pyrrolin-2-ones 19 in the presence of polyoxometalate immobilized on MOF-5 through the one-pot pseudofour-component reaction of dialkyl acetylenedicarboxylate 1, amines 2 and aldehyde 6 in methanol at room temperature (Scheme 7). [16] Based on chemical knowledge, pyrrols cores have recently received the attention because of their pharmaceutical field such as anti-oxidant, antitumor, antibacterial, anti-HIV, anti- ). [17] Substituted pyrroles 23 were synthesized from the reaction of dialkyl acetylene dicarboxylate 1, α-oximinoketone 22 and triphenylphosphine 15 using ionic liquid (1-methyl-3-butylimidazolium bromide [mbim]Br) at room temperature in 2018 by Shahvelayati and co-workers.…”

Section: Pyrrolesmentioning

confidence: 99%

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

2022

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Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di-ester in which the ester groups are conjugated with a carbon-carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels-Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016)(2017)(2018)(2019)(2020)(2021)(2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.

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“…In the current research methods of synthesizing pyrrole-2-ones, different catalysts have been developed and used, such as organic catalysts: fluoroimine thiocarbonate, 14 thioureas and phosphoric acids, 15 and benzoic acid. 16 Besides, inorganic catalysts including silica supported ferric chloride (SiO 2 –FeCl 3 ), 17 polyoxometalate immobilized on MOF-5, 18 magnetic CoFe 2 O 4 nanoparticles, 19 NiFe 2 O 4 nanoparticles, 20 acidic ionic liquid triethylammonium hydrogen sulfate ([Et 3 NH][HSO 4 ]), 21 and Lewis acid Yb(OTF) 3 22,23 have also been studied.…”

Section: Introductionmentioning

confidence: 99%