A novel three-step synthesis of 3-aryl β-carbolin-1-ones from non-indole starting materials has been developed. The two nitrogen atoms in β-carbolin-1-one were introduced efficiently by Michael addition of ethyl acetamidocyanoacetate to chalcone. The desired pyridone and indole rings were assembled by an intramolecular ketone-nitrile annulation mediated by aqueous HCl-HOAc and a Cu(i)-catalyzed intramolecular N-arylation of the amide, respectively. The target compounds were found to possess significant activity against tumor cell proliferaton.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry