Synthesis of a coronene analogue containing an amide bond by Pd-mediated intramolecular C[sbnd]C bond formation of 2-halogenated 4-(alkylamino)benzoic acid cyclic trimer.

• The synthesis of 2-halogenated 4-(isobutylamino)benzoic acids was reported. • Cyclic triamides of the 4-aminobenzoic acids were synthesized by condensation. • Pd-mediated C C bond formation of the cyclic triamide gave a coronene analogue. A coronene analogue containing amide linkage was synthesized from a halogenated cyclic triamide by palladium-mediated intramolecular C C bond formation. The cyclic triamide was formed from the condensation of 2-chloro-4-(isobutylamino)benzoic acid in the presence of dichlorotriphenylphosphorane in 1,1,2,2-tetrachloroethane. By contrast, the condensation of 2-bromo counterpart required silicon tetrachloride in pyridine. The intramolecular C C bond formation, which yielded the target coronene analogue, occurred during the reaction of bromo-substituted cyclic triamide with palladium(II) acetate, triphenylphosphine, and potassium carbonate in N , N -dimethylformamide. [ABSTRACT FROM AUTHOR]