Palladium-catalyzed intramolecular C–N coupling: Facile synthesis of tetracyclic C(3)-aminoisoindolinones

Abstract

Herein, we report a new methodology to access tetracyclic heterocyclic compounds incorporating fused isoindolinone and benzimidazoline or isoindolinone and quinazoline motifs. The palladium-(II) catalyzed intramolecular Buchwald-Hartwig C–N coupling involving the C(3) amino and the N(2) 2-bromophenyl groups provided coveted heterocycles in excellent yields. The methodology is versatile, highly efficient, and has a wide scope for the synthesis of a range of medicinally important tetracyclic C(3)-aminoisoindolinones.

Graphical Abstract

Keywords:

• Aminoisoindolinones
• Buchwald–Hartwig
• C–N Coupling
• tetracyclic

Acknowledgements

HSPR thanks Pondicherry University (PU) for the financial support to carry out the work described here. We thank DST-FIST and UGC-SAP for the instrumentals given to the Department of Chemistry. JP thanks UGC-RGNF for fellowship. We thank the Central Instrumentation Facility, PU for spectral and analytical data.