Intramolecular low-temperature 1,3-dipolar cycloadditions of nitrones: synthesis of chromano-heterocycles

In contrast to the reported facile intramolecular 1,3-dipolar cycloadditions of in-situ generated nitrone on heterocyclic systems, reactions of 2-(N-allyl/crotyl/cinnamyl-anilino)-3-formylchromones with N-phenyl-/methylhydroxylamine under comparable conditions, afford fused isoxazolidines only in low to moderate yields; the corresponding amides derived from rearrangement of in situ generated nitrones are formed as major products. However, when reactions were carried by stirring the reactants at an ice-cold temperature in dichloromethane, highly stereoselective intramolecular 1,3-dipolar cycloadditions lead to novel fused isoxazolidines in high yields (80–90%).

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide