Synthesis of Novel Pyrrolo-[3,2-c]quinolines via Iron-Catalyzed Cross-Coupling Reaction of Grignard Reagents

Abstract

Cross-coupling reaction of alkyl and aryl magnesium halides with 4-chloro-pyrrolo-[3,2-c]quinoline in the presence of a catalytic amount of iron salt is described. The reactions are completed in 30 min, resulting in moderate to excellent yields of 52–94% in a tetrahydrofuran (THF)–N-methylpyrrolidinone (NMP) solvent mixture.

Keywords:

• Cross-coupling
• imidoyl chloride
• iron catalysis
• nitrogen heterocycles
• organomagnesium reagents

ACKNOWLEDGMENT

We thank the Ministère de l'Education Nationale, de la Recherche et de la Technologie (MENRT), the Centre National de la Recherche Scientifique (CNRS), and la Ligue contre le Cancer for financial support.

Notes

^a Isolated yield after purification on column chromatography;

^b The product was recovered by crystallization from CH₂Cl₂.