Titanocene(III)-Mediated 5‑exo-trig Radical Cyclization: En Route to Spirooxindole-Based Tetrahydrofuran and Bicyclic Lactone
journal contributionposted on 11.12.2019, 13:10 authored by Jothi Lakshmi Nallasivam, Tushar Kanti Chakraborty
The isatin core system is of immense importance due to the highly reactive prochiral C-3 position, which paves an easy way to construct large arrays of spirooxindole heterocyclic motifs. Herein, we depict an isatin-derived and 3,3′-disubstituted oxindole-appended epoxy-acrylate undergoing Cp2Ti(III)Cl-mediated reductive oxirane-ring opening with concomitant intramolecular 5-exo-trig radical cyclization leading to tetrahydrofuran-based oxa-spirooxindole systems. The fused spirooxindole structural feature is embedded in many natural products and tends to exhibit a wide spectrum of biological activities. The presence of more than one quaternary center and the availability of multiple functional groups like hydroxyl, ester, or lactone in the resultant products expand the scope of synthetic applications of the newly acquired oxa-spirooxindole molecules.
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exhibitoxirane-ringSpirooxindole-Based TetrahydrofurancyclizationCyclizationTiisatin core systemarrayavailabilityBicyclic Lactoneepoxy-acrylateEn RouteTitanocenepresencetetrahydrofuran-based oxa-spirooxindole systemsesterscopelactonequaternary centerreductiveopeningimportancespectrumintramolecular 5- exo-trigreactive prochiral C -3 positionapplicationoxa-spirooxindole moleculesoxindole-appendedRadicalHereindisubstitutedisatin-derivedCpspirooxindole heterocyclic motifshydroxyl