Isoxazoline compounds are used as important intermediates for the synthesis of organic molecules, which are widely used in the chemical and life science industries. Oxime-participating cyclization has emerged as an efficient strategy for the construction of isoxazolines. This review is devoted to highlighting the main achievements (since 2010) in the development of methodologies for the synthesis of isoxazolines. According to the reaction mechanism, the oxime-participating synthesis of isoxazolines can be mainly classified into four reaction types: iminoxyl radical-initiated intramolecular cyclization, intermolecular radical addition-initiated cyclization, intramolecular nucleophilic cyclization, and [3 + 2] cycloaddition. Meanwhile, miscellaneous examples are also illustrated, such as [2 + 2 + 1] cycloaddition. Representative reactions will be discussed for each of the highlighted synthetic strategies. In addition, the enantioselective synthesis of isoxazolines is also illustrated in this review.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/d0ob00963f | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs.
J Org Chem
January 2025
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.
View Article and Find Full Text PDFSynthesis of Pyrrolidine-2-ylidenes from Isoxazolines and Allenes.
J Org Chem
December 2024
Department of Chemistry, University of Illinois Chicago, 845 West Taylor Street, MC 111, Chicago, Illinois 60607, United States.
A diastereoselective addition and rearrangement reaction has been developed for the synthesis of pyrrolidine-2-ylidenes from N-isoxazolines and electron-deficient allenes. This method proceeds via the rearrangement of a proposed -alkenylisoxazoline intermediate to generate densely functionalized pyrrolidine-2-ylidenes under simple catalyst-free conditions that tolerate ketone substituents and install relative stereochemistry at positions 3 and 4 of the heterocycle. Reaction optimization and the substrate scope are described in addition to studies evaluating the reactivity of the -dione and enaminone groups of the products.
View Article and Find Full Text PDFGeneral Alkene 1,2--Cyano-Hydroxylation Procedure Via Electrochemical Activation of Isoxazoline Cycloadducts.
J Am Chem Soc
November 2024
Department of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Stereoselective alkene 1,2-difunctionalization is a privileged strategy to access three-dimensional C(sp)-rich chiral molecules from readily available "flat" carbon feedstocks. State-of-the-art approaches exploit chiral transition metal-catalysts to enable high levels of regio- and stereocontrol. However, this is often achieved at the expense of a limited alkene scope and reduced generality.
View Article and Find Full Text PDFManganese-Mediated Cascade Radical Oxidative Cyclization/1,6-Conjugate Addition of Unsaturated Oximes with p-Quinone Methides: Facile Access to β,β-Diarylmethine Substituted Isoxazolines.
Chem Asian J
November 2024
Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune, 411 008, India.
Article Synopsis
- * The process involves an oxidative cyclization and a 1,6-conjugate addition of unsaturated oximes to p-quinone methides, resulting in the formation of important chemical bonds.
- * High yields of isoxazolines with various functional groups were successfully achieved, showcasing the versatility of this synthetic approach.
1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (-)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing.
Int J Mol Sci
October 2024
Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
The cycloaddition of nitrile oxides and nitrilimines to one or both of the C=C double bonds of caryophyllene is described. The possibility of introducing five-membered fused and spiro-linked heterocycles into the structure of sesquiterpenes by the 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrilimines to caryophyllene was demonstrated. As a result of these reactions, pharmacophore fragments of isoxazoline and pyrazoline are introduced into the structure of caryophyllene, which leads to an increase in the conformational rigidity of the molecule.
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!