A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-aminobenzamides with aryl iodides leading to quinazolinones.

Abstract The first heterogeneous carbonylative annulation of 2-aminobenzamides with aryl iodides was achieved in N,N- dimethylformamide (DMF) at 120 °C under 10 bar of carbon monoxide by using an MCM-41-immobilized bidentate phosphine palladium(II) complex [MCM-41-2P-Pd(OAc) 2 ] as catalyst and 1,8-diazabicycloundec-7-ene (DBU) as base, yielding a wide variety of quinazolinone derivatives in good to excellent yields. The new heterogeneous palladium catalyst can easily be prepared by a simple procedure from commercially readily available reagents, and recovered by filtration of the reaction solution, and recycled up to eight times without significant loss of activity. Graphical abstract Image 1 Highlights • The new MCM-41-2P-Pd(OAc) 2 complex could be easily prepared by a simple procedure. • This Pd catalyst exhibited the same catalytic activity as the Pd(OAc) 2 /DPPP system. • The reaction generated a variety of quinazolinones in good to excellent yields. • This Pd catalyst can be recycled up to eight times almost without loss of activity. • Our catalytic system provides a practical route for the synthesis of quinazolinones. [ABSTRACT FROM AUTHOR]