Cyclohepta[b]indole Core Construction via the Michael Addition/Friedel–Crafts Condensation Sequence

Abstract

An approach to cyclohepta[b]indoles via the formal (4 + 3) annulation of readily synthesized 2-indolyl-derived 1,3-dicarbonyl compounds to acrolein and enones was developed. The process is initiated by catalytic Michael addition, wherein the adduct was generated in situ. The subsequent addition of a Bro̷nsted acid catalyst triggers a cascade process that includes intramolecular Friedel–Crafts hydroxylalkylation followed by dehydration. The cascade reaction is relatively undemanding since even degrading chloroform is able to initiate it. The obtained tetrahydrocyclohepta[b]indoles were prone toward easy dimerization, underscoring the high reactivity of the double bond in the seven-membered ring.