Ruthenium(ii)-catalyzed C−H/C−H(4+2) annulation of 2-aryl-N-heterocycles with vinylene carbonate

Abstract

A ruthenium(II)-catalyzed direct C−H/C−H (4+2) annulation of 2-aryl-N-heterocycles such as 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones, 2-arylimidazo[1,2-a]pyridines, 2-aryl-2H-indazoles and 2-arylquinolin-4(1H)-ones with vinylene carbonate has been described. This one-pot cascade strategy provided the diversely substituted fused-polyheterocycles such as 7H-benzo[h]pyrido[2,1-b]quinazolin-7-ones, naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines, indazolo[2,3-a]quinolines and benzo[c]acridin-7(12H)-ones in moderate to excellent yields. The developed protocol exhibited a broad substrate scope with good functional group tolerance and acid/base-free conditions. Based on a preliminary mechanistic investigation, a tentative mechanism of Ru(II)-catalyzed (4+2) annulation reaction has been proposed.