biostudies-literaturePrabhakaran PCouncil of Scientific and Industrial Research, India10263-10276https://www.ebi.ac.uk/biostudies/studies/S-EPMC9050375biostudies-literatureUnknown10(17)A convenient and efficient method for the regioselective macrocyclization of triazole bridged spiropyrrolidine-oxindole, and bis-spiropyrrolizidine-oxindole derivatives was accomplished through intra and self-intermolecular [3 + 2] cycloaddition of azomethine ylides. The chalcone isatin precursors 9a-i required for the click reaction were obtained from the reaction of <i>N</i>-alkylazidoisatin 4 and propargyloxy chalcone 8a-i which in turn were obtained by the aldol condensation of propargyloxy salicylaldehyde 6 and substituted methyl ketones 7a-i. The regio- and stereochemical outcome of the cycloadducts were assigned based on 2D NMR and confirmed by single crystal XRD analysis. High efficiency, mild reaction conditions, high regio- and stereoselectivity, atom economy and operational simpRSC advancesRegio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.PMC905037509/115(0775)/2014 EMR-IRajakumar PPrabhakaran PfalseRegio- and stereoselective synthesis of spiropyrrolidine-oxindole and bis-spiropyrrolizidine-oxindole grafted macrocycles through [3 + 2] cycloaddition of azomethine ylides.A convenient and efficient method for the regioselective macrocyclization of triazole bridged spiropyrrolidine-oxindole, and bis-spiropyrrolizidine-oxindole derivatives was accomplished through intra and self-intermolecular [3 + 2] cycloaddition of azomethine ylides. The chalcone isatin precursors 9a-i required for the click reaction were obtained from the reaction of <i>N</i>-alkylazidoisatin 4 and propargyloxy chalcone 8a-i which in turn were obtained by the aldol condensation of propargyloxy salicylaldehyde 6 and substituted methyl ketones 7a-i. The regio- and stereochemical outcome of the cycloadducts were assigned based on 2D NMR and confirmed by single crystal XRD analysis. High efficiency, mild reaction conditions, high regio- and stereoselectivity, atom economy and operational simp2020-01-01T00:00:00Z2020 Mar2025-04-19T09:17:58.887Z2025-04-19T09:17:58.887ZS-EPMC90503753549861310.1039/c9ra10463a