An environmentally benign multi-component reaction: Highly regioselective synthesis of functionalized 2-(diarylphosphoryl)-1,2-dihydro-pyridine derivatives

Li, Kun; Lv, Ying; Lu, Zihan; Yun, Xing-Han; Yan, Sheng‐Jiao

doi:10.1016/j.gresc.2021.10.008

Cited by 27 publications

(18 citation statements)

References 54 publications

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“…Over the past 10-15 years, not only selectivity parameters and overall yield of reaction products but also such factors as enhanced requirements to starting materials, reaction time, energy consumption, toxicity, etc., have acquired increasing significance in the assessment of the efficiency of chemical syntheses. 1,3-Diketones turned out to be excellent versatile intermediates in multicomponent reactions, in particular regio-and stereoselective, which is especially important in the synthesis of potentially biologically active compounds [7][8][9][10][11][12]. Moreover, 1,3diketones (β-diketones) are ubiquitous scaffolds found in many natural products, exhibiting a wide range of biological activities.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of heterocyclic derivatives as potential cytotoxic compounds evaluated toward hepatocellular and cervical carcinoma cell lines

Mohareb¹,

Ibrahim²

2022

Bull. Chem. Soc. Eth.

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ABSTRACT. Through the present work the 3-oxo-N,3-diphenylpropamide derivatives 5a,b were used to synthesize pridine, pyrazole and thiophene derivatives. 3-Phenylisoxazol-5(4H)-one produced from the reaction of ethyl benzoylacetate was used as the key starting compound for different multi-component reactions. The synthesized compounds were evaluated toward Hepatocellular carcinoma HepG2 and cervical carcinoma HeLa cell lines. Compounds 3b, 5b, 7b, 7d, 9c, 9d, 15e, 15f, 16b, 18b, 18e, 18f, 19e and 19f were the most cytotoxic compounds against the tested cell lines. The results obtained in this work encourage further work in the future to produce new cytotoxic compounds. KEY WORDS: Diphenylpropamide, 3-Phenylisoxazole, Pyran, Pyridine, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(1), 141-158. DOI:https://dx.doi.org/10.4314/bcse.v37i1.12

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Section: Introductionmentioning

confidence: 99%

Syntheses of heterocyclic derivatives as potential cytotoxic compounds evaluated toward hepatocellular and cervical carcinoma cell lines

Mohareb¹,

Ibrahim²

2022

Bull. Chem. Soc. Eth.

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“…One pot multicomponent reactions (MCRs) with high atom economy combinatorial chemistry has attracted great attention in recent years [1][2][3][4][5][6][7]. During MCRs, complex compounds are produced in a one pot from three or more reactants [8,9].…”

Section: Introductionmentioning

confidence: 99%

Introduction of Sb (V)-metalloid ion supported on mesoporous Nano- γ-alumina as an effective catalytic system for the synthesis of highly substituted tetrahydropyridines under ultrasonic and thermal conditions

Aghamohammadsadegh

Bamoniri

Mirjalili

2022

Preprint

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Background In this research work, Nano-γ-Al2O3/Sb(V) was synthesized and characterized as a heterogeneous Lewis acid catalyst. Fourier Transform Infrared Spectroscopy, Field Emission Scanning Electron Microscopy, Brunauer–Emmett–Teller plot, Energy Dispersive X-ray Spectroscopy and Thermo Gravimetric Analysis were used to characterization of Nano-γ-Al2O3/Sb(V). Tetrahydropyridine, is known as the nuclear structure in some natural products and drugs. Results Poly substituted tetrahydropyridine-3-carboxylates are synthesized via one pot multi component reaction of ethyl acetoacetate, aldehyde and aniline derivative. This present study introduces synthesis of tetrahydropyridine-3-carboxylate in the presence of Nano-γ-Al2O3/Sb(V) under ultrasonic and thermal conditions. Conclusion Compared to the previously reported methods, our attitude is suitable and offers several benefits such as milder reaction conditions, shorter reaction time, excellent yields and use of reusable catalyst.

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“…2-(Pyridine-2-yl)acetate derivatives are also versatile building blocks ,, used in the synthesis of a variety of different heterocycles. In this paper, we reacted 2-(pyridine-2-yl)acetate derivatives with maleimides through a cascade reaction to test this model reaction in the presence of different catalysts and oxidants.…”

Section: Introductionmentioning

confidence: 99%

Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones

Zhao

et al. 2022

J. Org. Chem.

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A novel protocol for the construction of highly functionalized indolizine derivatives, that is, 1H-pyrrolo[3,4-b]indolizine-1,3-diones (PIZDOs, 3) from 2-(pyridine-2-yl)acetates and maleimides via a regioselective oxidative [3 + 2] annulation was developed. The cascade oxidative reaction was enabled by heating a mixture of the two substrates in the presence of Ag2CO3 as an oxidant and Cu(OAc)·H2O as a catalyst in chlorobenzene. Consequently, a series of PIZDOs 3 were synthesized with high regioselectivity in moderate yields. This protocol can be used in the synthesis of functionalized PIZDOs via the one-pot oxidative annulation reaction rather than through multistep reactions, which is suitable for both combinatorial and parallel syntheses of PIZDOs.

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An environmentally benign multi-component reaction: Highly regioselective synthesis of functionalized 2-(diarylphosphoryl)-1,2-dihydro-pyridine derivatives

Cited by 27 publications

References 54 publications

Syntheses of heterocyclic derivatives as potential cytotoxic compounds evaluated toward hepatocellular and cervical carcinoma cell lines

Syntheses of heterocyclic derivatives as potential cytotoxic compounds evaluated toward hepatocellular and cervical carcinoma cell lines

Introduction of Sb (V)-metalloid ion supported on mesoporous Nano- γ-alumina as an effective catalytic system for the synthesis of highly substituted tetrahydropyridines under ultrasonic and thermal conditions

Cu-Catalyzed Oxidative [3 + 2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones

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