Decarboxylative 1,3-dipolar cycloadditions of l-proline

RSC Advances, Journal Year: 2024, Volume and Issue: 14(12), P. 8481 - 8501

Published: Jan. 1, 2024

1,3-Dipolar cycloaddition is one of the important chemical reactions between a 1,3-dipole and dipolarophile to construct five-membered heterocyclic compound. As an available α-amino acid reactant, l-proline extensively used in 1,3-dipolar reactions. A diverse spectrum bioactive spiro fused N-heterocycles obtained through this synthetic approach. In review, we have described use synthesis various spiro- scaffolds.

Language: Английский

Heteroatom-Controlled Three-Component [4 + 3] or [3 + 2] Annulation of Isatin-Derived Azomethine Ylide with Azadiene: Selective Synthesis of Spirooxindole-diazepines and Density Functional Theory Studies

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8945 - 8950

Published: Oct. 9, 2024

A novel three-component [4 + 3] annulation reaction of isatin-derived azomethine ylides with azadienes was developed for the first time to efficiently synthesize spirooxindole-diazepines incorporating a benzothiophene moiety under catalyst-free conditions. Effects heteroatom azadiene on chemoselectivity investigated. With use bearing benzofuran as substrate, dominant pathway changed an α-[3 2] annulation. When indenone used, distinct γ-[3 observed. Density functional theory calculations revealed that delicate balance between kinetic accessibility and thermodynamic driving force controlled competition different reactions.

Language: Английский