The Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,4 asymmetric induction in an Ugi reaction as well as the first example of diastereoselective Ugi reaction of seven membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170203 | PMC |
| http://dx.doi.org/10.3762/bjoc.7.109 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction.
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 PDFOne-Step Synthesis for Orn-Val with High Molecular Weight and Low Polydispersity by Ugi Four-Component Condensation.
ACS Biomater Sci Eng
November 2024
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 PDFCore-shell structured magnetite carboxymethyl cellulose for cervical cancer treatment by maintaining methotrexate serum concentration.
Int 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 PDFModular Design and Scaffold-Synthesis of Multi-Functional Fluorophores for Targeted Cellular Imaging and Pyroptosis.
Angew 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 PDFSynthesis of spiroindolenines through a one-pot multistep process mediated by visible light.
Beilstein 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.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!