Palladium-Catalyzed Synthesis of Heterocyclic Ring Systems by Combination of Regioselective C-C with Twofold C-N Couplings

The combination of regioselective palladium-catalyzed C-C with twofold C-N couplings allows for the synthesis of a variety of heterocyclic ring systems. Starting materials include thiophenes arid benzothiophenes, pyrroles and indoles, furans and benzofurans, pyridines, quinolines and quinoxalines, complex heterocyclic systems and benzophenone derivatives. The products are in many cases complex polyheterocyclic systems, which are not readily available by other methods or, in a number of cases, were not described in the literature before. They are of pharmacological relevance or interesting in the field of material science. Products include thieno[3,2-b:4,5-b']diindoles, thieno[3,2-b]indoles, thieno[3,4-b]indoles, 5,10-dihydroindolo[3,2-b]indoles, furo[3,2-b:4,5-b']diindoles, benzo[4,5]furo[3,2-b]indoles, 5,7-dihydropyrido[3,2-b:5,6-b']diindoles, 5,7-dihydropyrido[2,3-b:6,5-b']diindotes, alpha- , beta-, gamma- and delta-carbolines, indolo[3,2-b]quinolines, indolo[2,3-b]quinolines, indolo[3,2-c]quinolines, indoloquinoxalines, pyrido[2',1':2,3]imidazo[4,5-b]indoles, thiadiazolo[2',3':2,3]imidazo[4,5-Nindoles, benzo[b]carbazolediones, acridones and thieno[3,2-b]quinolones.

Automated summary

The combination of regioselective palladium-catalyzed C-C with twofold C-N couplings allows for the synthesis of a variety of heterocyclic ring systems, including complex polyheterocyclic systems, which are of pharmacological relevance or interesting in the field of material science.