One-pot access to indolo[2,3-b]quinolines by electrophile-triggered cross-amination/Friedel-Crafts alkylation of indoles with 1-(2-tosylaminophenyl)ketones

Abstract

Activation of C2 and C3 of indoles by molecular iodine (I(2)) and base followed by in situ reaction with 1-(2-tosylaminophenyl)ketones or 2-tosylaminobenzaldehyde can afford highly substituted indolo(2,3-b)quinolines in moderate to excellent yields (up to 99%). The reaction provides a metal-free selective difunctionalization of indoles. The synthetic potential of the protocol has been illustrated by the synthesis of neocryptolepine and its 11-methyl analogue.