Base-Mediated Tandem Michael Addition and SuFEx Cyclization for the Synthesis of Sultone-Containing Spirooxindoles.
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Govender KB, Simelane SB, Chetty LC, Kruger HG, Govender T, Arvidsson PI, Naicker T
ACS Omega 10 (39) 45516-45523 [2025-10-07; online 2025-09-28]
Sulfur-containing spirooxindoles are recognized for their significant biological activity, yet accessing these compounds with diverse heteroatoms in the spirocyclic core has remained challenging. This study introduces a simple and efficient base-mediated tandem Michael addition reaction and SuFEx cyclization to synthesize novel sultone-containing spirooxindoles. The transformation occurred in a green solvent, which proved essential in suppressing side reactions, leading to the successful synthesis of 20 novel sultone-spirooxindoles and two sulfonates that are resistant to cyclization. Additionally, a chiral variant of the reaction was explored, laying the groundwork for the future development of enantioselective methods.
PubMed 41078771
DOI 10.1021/acsomega.5c05571
Crossref 10.1021/acsomega.5c05571