Abstract
An efficient, transition-metal-free protocol employing I2/Cs2CO3 for the synthesis of thiosulfonate containing 2-iminoindolin-3-ones motifs has been developed from C-3 phenylthio indoles. The reaction proceeded through intramolecular cyclization involving C-N bond formation, leading to the formation of indole-fused benzothiazines as a key intermediate. Remarkably, Cs2CO3 played a crucial role in the reaction as an oxygen source, enabling oxidative rearrangement with [1,4]-sulfonyl migration to furnish the final products with the formation of multiple functional groups such as C═O, C═N, and S-SO2.
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