Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones?

New Journal of Chemistry Pub Date: 2020-05-04 DOI: 10.1039/D0NJ00887G

Abstract

The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2–5 min. The dicyclic spiropyrrolidine oxoindole was smoothly acquired in moderate to excellent yields (35–95%) with high diastereoselectivities (>20?:?1 dr).

Graphical abstract: Rapid abnormal [3+2]-cycloaddition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones
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