Metal-free, oxidative four-component Ugi reactions (U-4CRs) were conducted to synthesize dipeptides from two different amines, isocyanides, and carboxylic acids using 2,4,6-trihydroxybenzoic acid catalyst in O atmosphere. The organocatalytic U-4CRs proceed via oxidative cross-coupling of benzylamines with other aliphatic or aromatic amines to form imines, followed by condensation with isocyanides and carboxylic acids. The U-4CRs via cross-coupling of amines are rare, and the simple, metal-free procedures are advantageous for further applications in drug and heterocycle syntheses.
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http://dx.doi.org/10.1021/acs.joc.9b01422 | DOI Listing |
Beilstein J Org Chem
November 2024
Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo. Ciudad Universitaria, C.P. 58030, Morelia, Michoacán, Mexico.
A series of 1,5-disubstituted tetrazole-indole hybrids were synthesized via a high-order multicomponent reaction consisting of an Ugi-azide/Pd/Cu-catalyzed hetero-annulation cascade sequence. This operationally simple one-pot protocol allowed high bond-forming efficiency and creating six new bonds (two C-C, three C-N, and one N-N). Additionally, the products were evaluated against breast cancer MCF-7 cells, finding moderate activity in the compounds substituted with fluorine and chlorine.
View Article and Find Full Text PDFACS Biomater Sci Eng
January 2025
Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Basic amino acid alternating copolymers exhibit exceptional antimicrobial properties and biosafety, yet their application is restricted by the complexity of the synthesis process and low molecular weight ( = 1000). In this study, we synthesized a basic amino acid alternating copolymer (Orn-Val) in only one step by the Ugi four-component condensation (Ugi'4CC), achieving high molecular weight ( = 20,000) and narrow polydispersity (PDI ≤ 1.10).
View Article and Find Full Text PDFInt J Biol Macromol
January 2025
Polymer Research Laboratory, Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran; Research Center for Pharmaceutical Nanotechnology, Biomedicine Institute, Tabriz University of Medical Science, Tabriz, Iran. Electronic address:
In this work, we attempted to improve the properties of magnetite carboxymethyl cellulose nanoparticles (Mag CMC NPs) through Ugi multicomponent reaction (MCR) to obtain magnetite carboxymethyl cellulose@functionalized carboxamide nanoparticles (Mag CMC@FCA NPs) as a new nano bio-carrier. Typically, at first Mag CMC NPs prepared by the co-precipitation method. Then by performing the Ugi MCR on Mag CMC NPs, the Mag CMC@FCA NPs achieved better properties in swelling ratio, loading efficiency and loading capacity.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
Physical and Synthetic Biology, Faculty of Biology, Ludwig-Maximilians-Universität München, Großhadernerstr. 2-4, 82152, Planegg-Martinsried, Germany.
Fluorophores are essential tools for optical imaging and biomedical research. Their synthetic modification to incorporate new functions, however, remains a challenging task. Conventional strategies rely on linear synthesis in which a parent framework is gradually extended.
View Article and Find Full Text PDFBeilstein J Org Chem
October 2024
Department of Chemistry and Industrial Chemistry, University of Genoa, Via Dodecaneso 31, 1646 Genova, Italy.
Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of -aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine.
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