Efficient Synthesis of Fully Substituted Pyrrolidine-Fused 3-Spirooxindoles via 1,3-Dipolar Cycloaddition of Aziridine and 3-Ylideneoxindole

Abstract

Drug-like spirocyclic scaffolds have been prepared by fusing fully functionalized pyrrolidine with oxindoles in an approach based on 1,3-dipolar cycloaddition. Reaction between aziridine and 3-ylideneoxindole generated diverse spirooxindole-pyrrolidines in good yield (up to 95%) with high diastereoselectivity (up to >20:1). The reaction also proceeded smoothly with several other synthetically useful activated trisubstituted olefins. The mild reaction conditions, short reaction times, and high tolerance for various substitutions make this approach attractive for constructing pharmacologically interesting spiro-architectures.

Synthesis of 1,2,3-Triazole 5-Chloroisatin Derivatives via Copper-Catalyzed 1,3-Dipolar Cycloaddition Reactions

“…Many azide compounds have mutagenic activities [33][34]. The chemistry of azides has therefore attracted the attention of many chemists, then many of the azide compounds play an important role in organic chemistry [35,36]. One of the most useful synthetic applications of the azides is the preparation of 1,2,3-triazoles by the 1,3-dipolar cycloaddition reaction of the azides with substituted alkenes.…”