Regioselective Alcoholysis and Hydrochlorination Reactions of Spiro‐Epoxy Oxindoles at the Spiro‐Centre: Synthesis of 3,3‐Disubstituted Oxindoles and Application for Anticancer Agents.

An efficient and highly regioselective BiIII catalyzed alcoholysis and Hydrochlorination reaction of spiro‐epoxy oxindole is demonstrated with alcohols and chlorine for easy access to 3,3‐disubstituted oxindoles. This protocol furnished alkyloxy and chlorinated products at the C3 spiro center of the epoxy ring in high yields up to 98 % with excellent regioselectivity > 99 %. The synthetic protocol was further exploited for the synthesis of the anti‐cancer active molecule, 1‐benzyl‐3‐(hydroxymethyl)‐3‐(phenylamino)indolin‐2‐one. Regioselective BiIII‐catalyzed alcoholysis and hydrochlorination reactions of spiro‐epoxy oxindoles offer an easy access to 3,3‐disubstituted oxindoles. These catalytic protocols give the alkoxy and chlorinated products at the C3 spiro center of the former epoxy ring in high yields (up to 98 %) and excellent regioselectivity (> 99 %). The synthetic protocol was further exploited for the synthesis of an anticancer active derivative. [ABSTRACT FROM AUTHOR]