Direct synthesis of highly fused perimidines by copper(I)-catalyzed hydroamination of 2-ethynylbenzaldehydes
A novel synthesis of highly fused perimidine derivatives was achieved in two steps from 2-alkynylbenzaldehydes. Copper-catalyzed annulation of 2-[(2-bromophenyl)ethynyl]benzaldehydes with 1, 8-diaminonaphthalene produced dihydroisoquinolino[2, 1-a]perimidines bearing a 2-bromophenyl group. Subsequent palladium-catalyzed C–H arylation provided dibenzo[1, 2:7, 8]quinolizino[3, 4, 5, 6-kla]perimidine derivatives in moderate to good yields.
Tetrahedron 67 (29), 5168-5175, 2011-07