Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

Wang, Zeyou; Shen, Guodong; Huang, Xianqiang; Gong, Shuwen; Yang, Bingchuan; Sun, Zhenzhen; Zhang, Zuhao; Liu, Wanxing

doi:10.1007/s40242-020-9019-3

Cited by 2 publications

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“…Tetrahydroquinolines are widely found in natural products and are important pharmacophores bearing various properties, such as excellent antithrombotic efficacies in rabbit thrombosis models. 81 A. A. Sara et al…”

Section: Special Topic Synthesis 413 Synthesis Of Tetrahydropyrazolo[4′3′:56] Pyrano[34-c]quinolonesmentioning

confidence: 99%

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Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

et al. 2021

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The Diels-Alder reaction has long established its high rank in the toolbox of any natural product chemist. The tremendous toleration of building blocks of various complexity and derivatization degree, as well as the enablement of furnishing six-membered rings with well-defined stereochemistry represents its main features and advantages. In recent years, many total syntheses of natural products relied at some point on the use of a [4+2]-cycloaddition step. Among classic approaches, several modifications of the Diels-Alder reaction, such as hetero-Diels-Alder reactions, dehydro-Diels-Alder reactions or domino-Diels-Alder reactions have been employed to extend the scope in the synthesis of natural products. Our review covers the application of the Diels-Alder reaction in natural product syntheses from 2017 to 2020, as well as selected methodologies which were inspired by, or could be used to access natural products.

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Section: Special Topic Synthesis 413 Synthesis Of Tetrahydropyrazolo[4′3′:56] Pyrano[34-c]quinolonesmentioning

confidence: 99%

“…Talatisamine, isolated from Aconitum species shows a high biological activity as an analgesic, anti-inflammatory, antipyretic, antiepileptic and hypotensive agent. Furthermore, talatisamine serves as a potent antiarrhythmic due to its selective inhibition of K + -channels 82.…”

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confidence: 99%

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

et al. 2021

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Insights into Quinoline in Context of Conventional versus Green Synthesis

Grover,

Singh,

Vaja

2023

COC

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A relatively new field dubbed "green chemistry" seeks to achieve sustainability at the molecular level. This topic has received a lot of interest in recent years because of its ability to fulfill both environmental and economic goals through non-hazardous chemical innovation. A number of substituted quinoline derivatives were synthesized using microwave irradiation (MW), light irradiation, the presence of a non-biodegradable and recyclable catalyst, the presence of nanoparticles under solvent-free conditions, or the use of a green solvent. High target compound yields, fast reaction times, a simple workup process, the ability to reuse the catalyst, and environmentally favorable settings are all advantages of this effective approach. This study explores the synthesis of quinoline, a versatile heterocyclic compound with widespread applications in pharmaceuticals, agrochemicals, and material science. The focus is on comparing conventional and green synthesis methods and evaluating their respective advantages, drawbacks, and environmental impacts. The transition from conventional to sustainable green methodologies highlights the significance of reducing waste, energy consumption and toxic reagents in quinoline synthesis.

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Ball-milling Synthesis of Tetrahydroquinolines via ‘One-pot’ Three-component Diels-Alder Reaction Catalyzed by Phosphotungstic Acid

Cited by 2 publications

References 42 publications

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

Recent Applications of the Diels–Alder Reaction in the Synthesis of Natural Products (2017–2020)

Insights into Quinoline in Context of Conventional versus Green Synthesis

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