A simple and practical method for the construction of 1,3,5-trisubstituted imidazolidine derivatives [3 + 2] cycloaddition reaction has been developed. This reaction could smoothly proceed between nonstabilized azomethine ylides generated and 2-benzothiazolamines to deliver a wide scope of differently substituted imidazolidines in high yields (up to 98%). The structure of one example was confirmed by X-ray single-crystal structure analysis.
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http://dx.doi.org/10.1039/d2ra04616d | DOI Listing |
J Org Chem
September 2023
Normandie Univ; UNILEHAVRE, URCOM, EA 3221, 25 rue Philipe Lebon, F-76600 Le Havre Cedex, France.
Electron-poor arenesulfonyloxypyridines are selectively dearomatized whether on the pyridine or on the phenyl group through 1,3-dipolar cycloaddition (1,3-DC) involving non-stabilized azomethine ylides (AMY). Electronic effects of substituents on the aromatic rings allow to induce the regioselectivity of the transformation. Novel pyrrolidinic polycyclic heterocycles are thereby produced under mild acidic conditions at room temperature.
View Article and Find Full Text PDFChemistry
September 2023
Univ Rouen Normandie, INSA Rouen Normandie, CNRS, Normandie Univ, COBRA, 76000, Rouen, France.
The photocatalyzed dearomative reaction between various electron-deficient aromatic compounds and a non-stabilized azomethine ylide is successfully performed in a flow system. Whereas the use of supported eosin as organic photocatalyst exhibits limited efficiency, turning to the soluble Rose Bengal allows to transform a broad range of substrates from hetarenes (indole, benzofuran, quinoline, pyridine) to naphthalenes and benzenes. This photocatalyzed (3+2) dearomative cycloaddition under green light irradiation provides a simple and efficient access to tridimensional pyrrolidino scaffolds with a tetrasubstituted carbon center at ring junction and can be performed in the friendly ethyl acetate.
View Article and Find Full Text PDFA simple and practical method for the construction of 1,3,5-trisubstituted imidazolidine derivatives [3 + 2] cycloaddition reaction has been developed. This reaction could smoothly proceed between nonstabilized azomethine ylides generated and 2-benzothiazolamines to deliver a wide scope of differently substituted imidazolidines in high yields (up to 98%). The structure of one example was confirmed by X-ray single-crystal structure analysis.
View Article and Find Full Text PDFNew J Chem
February 2022
Department of Chemistry and Centre for Green Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA.
1,3-Dipolar cycloaddition of nonstabilized azomethine ylides derived from α-C-H functionalization of tetrahydroisoquinoline for regio- and diastereoselective synthesis of spirooxindole-pyrrolidines is developed. A three-component reaction of readily available cyclic amine, aryl aldehydes, and olefinic oxindoles provides a pot, atom and step economy (PASE) approach for making spiro-heterocyclic compounds with biological interest.
View Article and Find Full Text PDFJ Org Chem
November 2021
Department of Chemistry, Indian Institute of Technology, Ropar, Rupnagar, Punjab 140001, India.
Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction of -heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins.
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