Synthesis of New 2,3-Disubstituted 4-Chloro-1-hydroxyindoles

摘要

The syntheses of new 2,3-disubstituted 4-chloro-1-hydroxyindoles were described. The conjugate nitro ketoester was reacted with various thiol and alcohol nucleophiles by the action of stannous chloride dihydrate through the unique processes of reduction of nitro group, intramolecular condensation, and addition of nucleophiles in one pot, to provide multisubstituted 1-hydroxyindoles. The reactions with thiol nucleophiles provided better results than those with alcohols, and, in particular, secondary and tertiary thiols provided best yields.