Four methodologies are reported for the regioselective synthesis of four series of regioisomer isoxazoles from cyclocondensation of β-enamino diketones and hydroxylamine hydrochloride. Regiochemical control was achieved by varying reaction conditions and substrate structure. The mild reaction conditions used to access 4,5-disubstituted, 3,4-disubtituted, and 3,4,5-trisubstituted regioisomer isoxazoles, as well as the pharmacological and synthetic potential of the products, make these novel methodologies very powerful.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9077875 | PMC |
| http://dx.doi.org/10.1039/c7ra13343j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Novel 3-chloro-6-nitro-1-indazole derivatives as promising antileishmanial candidates: synthesis, biological activity, and molecular modelling studies.
J Enzyme Inhib Med Chem
December 2022
College of Science, Physics Department, Alfaisal University, Riyadh, Saudi Arabia.
An efficient pathway was disclosed for the synthesis of 3-chloro-6-nitro-1-indazole derivatives by 1,3-dipolar cycloaddition on dipolarophile compounds and . Faced the problem of separation of two regioisomers, a click chemistry method has allowed us to obtain regioisomers of triazole-1,4 with good yields from 82 to 90% were employed. Also, the antileishmanial biological potency of the compounds was achieved using an MTT assay that reported compound as a promising growth inhibitor of .
View Article and Find Full Text PDFGold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.
ACS Catal
June 2021
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, U.K.
The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group.
View Article and Find Full Text PDFScope and Limitations of Boron Fluorescent Complexes from Stable Nitrile Oxides in ABPP Assays.
ACS Omega
April 2019
Department of Chemistry, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy.
Anthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reactions with 1-substituted-4-(prop-2-yn-1-yloxy)benzene affording the expected isoxazoles in good yields and as single regioisomers. N-O Bond cleavage and boron complexation afforded the corresponding boron complexes, derivatized with either a triple bond for click-chemistry applications or an oxime group for nitrile oxide 1,3-dipolar cycloaddition. The optical properties of these compounds show potential for employment as fluorescent tags in imaging techniques.
View Article and Find Full Text PDFAnthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reaction with propargyl bromide affording the expected isoxazole as single regioisomer, suitably synthetically elaborated and functionalized with a protected triple bond. The introduction of a bromine atom at the position C10 of the anthracene moiety allows for inserting a variety of aromatic and heterocyclic substituents through Suzuki coupling. A two-way synthetic route can lead to simple isoxazole derivatives or, after N-O bond reductive cleavage and BF complexation, enamino ketone boron complexes.
View Article and Find Full Text PDFDevelopment of methodologies for the regioselective synthesis of four series of regioisomer isoxazoles from β-enamino diketones.
RSC Adv
January 2018
Departamento de Química, Universidade Estadual de Maringá (UEM) 87030-900 Maringá PR Brazil
Four methodologies are reported for the regioselective synthesis of four series of regioisomer isoxazoles from cyclocondensation of β-enamino diketones and hydroxylamine hydrochloride. Regiochemical control was achieved by varying reaction conditions and substrate structure. The mild reaction conditions used to access 4,5-disubstituted, 3,4-disubtituted, and 3,4,5-trisubstituted regioisomer isoxazoles, as well as the pharmacological and synthetic potential of the products, make these novel methodologies very powerful.
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!