Relevant bibliographies by topics / Ugi-Knoevenagel three- and four-component products

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Academic literature on the topic 'Ugi-Knoevenagel three- and four-component products'

Author: Grafiati
Published: 11 December 2022
Last updated: 25 January 2023

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Journal articles on the topic "Ugi-Knoevenagel three- and four-component products"

1

Barreto, Angélica de Fátima S., Veronica Alves dos Santos, and Carlos Kleber Z. Andrade. "Consecutive hydrazino-Ugi-azide reactions: synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles." Beilstein Journal of Organic Chemistry 13 (December 5, 2017): 2596–602. http://dx.doi.org/10.3762/bjoc.13.256.

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Isocyanide-based multicomponent reactions (IMCRs) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Our strategy was accomplished in only three steps: first, a one-pot hydrazino-Ugi-azide four-component reaction; second a hydrazinolysis and finally an additional hydrazino-Ugi-azide reaction. This sequence provides the title compounds in moderate to excellent yields. The products synthesized herein contain functional groups within their structures that can be easily modified to obtain new acylhydrazino 1,5-disubstituted tetrazoles.
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2

Trinh, Trieu N., Eileen A. McLaughlin, Mohammed K. Abdel-Hamid, et al. "Quinolone-1-(2H)-ones as hedgehog signalling pathway inhibitors." Organic & Biomolecular Chemistry 14, no. 26 (2016): 6304–15. http://dx.doi.org/10.1039/c6ob00606j.

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A series of quinolone-2-(1H)-ones derived from a Ugi-Knoevenagel three- and four-component reaction were prepared exhibiting low micromolar cytotoxicity against a panel of eight human cancer cell lines known to possess the Hedgehog Signalling Pathway (HSP) components, as well as the seminoma TCAM-2 cell line.
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3

Lesma, Giordano, Fiorella Meneghetti, Alessandro Sacchetti, Mattia Stucchi, and Alessandra Silvani. "Asymmetric Ugi 3CR on isatin-derived ketimine: synthesis of chiral 3,3-disubstituted 3-aminooxindole derivatives." Beilstein Journal of Organic Chemistry 10 (June 18, 2014): 1383–89. http://dx.doi.org/10.3762/bjoc.10.141.

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An efficient Ugi three-component reaction of a preformed chiral ketimine derived from isatin with various isonitrile and acid components has been developed. The reactions proceeded smoothly and in a stereocontrolled manner with regard to the new center of the Ugi products due to the stereoinduction of the amine chiral residue. A wide variety of novel chiral 3,3-disubstituted 3-aminooxindoles were obtained, a selection of which were subjected to post-Ugi transformations, paving the way to application as peptidomimetics.
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4

Glavač, Danijel, Ivanka Jerić та Matija Gredičak. "Organocatalytic Synthesis of α,α–Diaryl Substituted α–Amino Acid Derivatives by an Interrupted Three-Component Ugi Reaction". Croatica chemica acta 92, № 2 (2019): 203–9. http://dx.doi.org/10.5562/cca3536.

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An organocatalytic interrupted three-component Ugi reaction for the synthesis of α,α–diaryl α–amino acid derivatives is described. The transformation proceeds with a range of isocyanides and 3-aryl isoindolinone alcohols using Brønsted acid catalysts to afford products in good to excellent yields. Based on the obtained results, a reaction mechanism is proposed and discussed.
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5

Capurro, Pietro, Lisa Moni, Andrea Galatini, Christian Mang, and Andrea Basso. "Multi-Gram Synthesis of Enantiopure 1,5-Disubstituted Tetrazoles Via Ugi-Azide 3-Component Reaction." Molecules 23, no. 11 (2018): 2758. http://dx.doi.org/10.3390/molecules23112758.

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Tetrazoles have been widely studied for their biological properties. An efficient route for large-scale synthesis of 1,5-disubstituted tetrazoles (1,5-DTs) is presented. The strategy exploits a reductive approach to synthetize a cyclic chiral imine substrate which is then converted into the target product through an Ugi-azide three-component reaction (UA-3CR). The final products are equipped with additional functionalities which can be further elaborated for the generation of combinatorial libraries of enantiopure heterocycles.
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6

Xu, Da-Zhen, Cheng-Bin Li, and Yu-Wei Li. "An Efficient and Ecofriendly Three-Component Reaction for the Rapid Synthesis of 2-Amino-4H-chromenes Catalyzed by a DABCO­-Based Ionic Liquid." Synthesis 50, no. 18 (2018): 3708–14. http://dx.doi.org/10.1055/s-0037-1610123.

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An efficient, economical, and green strategy for the construction of biologically relevant 2-amino-4H-chromene scaffolds via a tandem Knoevenagel–Pinner cyclization–Michael reaction has been successfully developed. In the presence of DABCO-based ionic liquids, two different 2-amino-4H-chromene derivatives, 2-amino-4-(indol-3-yl)-4H-chromenes and 2-amino-4-(pyrazol-4-yl)-4H-chromenes, were prepared in good to excellent yields (81–97%) within short reaction times under mild conditions. All the products are purified by simple crystallization. The catalyst could be recycled for at least five times.
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7

Foley, Christopher, Arthur Shaw, and Christopher Hulme. "Two-Step Route to DiverseN-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products." Organic Letters 18, no. 19 (2016): 4904–7. http://dx.doi.org/10.1021/acs.orglett.6b02383.

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8

Tshiluka, Ndivhuwo R., Mpelegeng V. Bvumbi, Unarine Tshishonga, and Simon S. Mnyakeni-Moleele. "Synthesis of new 5-benzylidene-hydantoin esters." Journal of Chemical Research 46, no. 4 (2022): 174751982211041. http://dx.doi.org/10.1177/17475198221104183.

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Compounds containing a hydantoin moiety are found in several medicines in clinical use. In this research, ethyl- and methyl-[2-(5-benzylidene)-2,4-dioxoimidazolidin-3-yl]acetyl esters are successfully synthesized over four reaction steps using conventional methods. The synthesis begins by subjecting hydantoin to a Knoevenagel condensation reaction with three different benzaldehydes to afford the penultimate products, which are further reacted with ethyl or methyl (bromoacetyl)alaninates, butanoates, valinates, and norvalinates to give the desired products as esters in low to moderate yields.
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9

Vázquez-Vera, Óscar, Daniel Segura-Olvera, Mónica Rincón-Guevara, et al. "Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization." Molecules 23, no. 8 (2018): 2029. http://dx.doi.org/10.3390/molecules23082029.

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A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before.
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10

Talpara, Pratik K., Guarang G. Dubal, and Viresh H. Shah. "Synthesis and Biological Evaluation of some Novel Pyrano[2,3-d]Pyrimidine Derivatives." International Letters of Chemistry, Physics and Astronomy 74 (June 2017): 9–14. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.74.9.

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The synthesis of novel Pyrano[2,3-d]pyrimidine derivatives, had been synthesized by three component domino Knoevenagel hetero Diels-Alder reaction. The products were assayed for their in vitro biological assay antibacterial activity against with two Gram-positive bacteria Staphylococcus aureus MTCC-96, Streptococcus pyogenes MTCC 443, two Gram-negative bacteria Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441 and three fungal strains Candida albicans MTCC 227, Aspergillus Niger MTCC 282, Aspergillus clavatus MTCC 1323 taking ampicillin, chloramphenicol, ciprofloxacin, norfloxacin, nystatin, and griseofulvin as standard drugs. Among the various synthesized heterocyclic compounds, 1b, 1c and 1g are display broad spectrum antibacterial and antifungal activities against both gram-positive and gram-negative bacteria as compared with standard drugs.
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Dissertations / Theses on the topic "Ugi-Knoevenagel three- and four-component products"

1

Nin, Brauer Martin Claudio [Verfasser], Ludger [Akademischer Betreuer] Wessjohann, and Thomas J. J. [Akademischer Betreuer] Müller. "New post condensation reactions of Biginelli three and Ugi four component products / Martin Claudio Nin Brauer. Betreuer: Ludger Wessjohann ; Thomas J. J. Müller." Halle, Saale : Universitäts- und Landesbibliothek Sachsen-Anhalt, 2015. http://d-nb.info/1079217614/34.

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2

Trinh, Nguyen Trieu. "Small molecule inhibitors of the hedgehog signalling pathway as cancer suppressing agents." Thesis, 2016. http://hdl.handle.net/1959.13/1337980.

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Research Doctorate - Doctor of Philosophy (PhD)<br>The HSP plays a pivotal role in the spatial and temporal regulation of cell proliferation and differentiation. Conversely aberrant Hh signalling is involved in Gorlin syndrome, basal cell carcinoma (the most common cancer in the world), and more than one third of all human medulloblastoma cases. In all of these cases, it is believed that deregulated Hh signalling leads to increased cell proliferation and tumour formation. Inhibition of the Hedgehog Signalling Pathway, is a recently validated anti-cancer drug target, with vismodegib (GDC-0449, Erivedge®) and sonidegib (LDE225, Odomzo®), approved by the U.S. Food and Drug Administration for treatment of early and advanced basal cell carcinomas. We developed three new scaffolds of small molecule inhibitors of the HSP. The first scaffold consisted of 11 quinolone-2-(1H)-ones developed from a sequential Ugi-Knoevenagel reaction pathway (Chapter 3). These analogues not only express their anti-hedgehog activity through the significant inhibition of Gli₂ at both <i>gene</i> and protein expression in SAG-activated Shh LIGHT 2 cells at 10 and 25 μM, respectively, but are able to suppress a panel of nine human HSP expressing cancer cells (GI₅₀ from 2.9 to 18.0 μM). Whilst the exact mechanism remains to be determined, it is probable the inhibition observed is occurring downstream of Smo, due to its activity in the presence of SAG, a potent Smo activator. Subsequent second and third generation analogues were developed on the quinolone-2-(1H)-one pharmacophore, which highlighted the importance of a C3-tethered indole moiety. These new scaffolds were built on tryptophan (9 analogues, Chapter 4) and benzo[1,3]dioxol-5-ylmethyl-[2-(1H-indol-3-yl)-ethyl]-amine derivatives (11 analogues, Chapter 4) displaying superior inhibitory activity against Gli protein expression with the best inhibitors displaying submicromolar IC₅₀ (Chapter 4). Noteworthy, active compounds from the second and third libraries displayed inhibitory activity downstream of Smo, which circumvents the resistance issues experienced by the Smo inhibitors currently in use. We discovered the fourth library of 1,3-thiazine-6-phenylimino-5-carboxylates in a multicomponent one pot synthesis (12 analogues, Chapter 5). These analogues display structural similarities to HPI-1, a non-selective Gli inhibitor, and thus may present themselves as HSP inhibitors. Current biological evaluation is going on to investigate their anti-hedgehog properties.
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