An efficient and practical approach for the synthesis of indoloquinolines and indolo/pyrroloquinoxalines via a Cu-catalyzed Ugi-C/Ugi-N-arylation sequence

Abstract

A Cu-catalyzed tandem transformation of Ugi adducts through CH/NH bond functionalization reactions was reported for synthesizing a broad spectrum of indolo/pyrrolo-[1,2-a]quinoxaline-6/4-carboxamide, 7H-indolo[2,3-c]quinoline-6-carboxamide, and 1-(cyclohexylamino)-14H-indolo[2,3-c][1,4]oxazino[4,3-a]quinolin-4(3H)-one derivatives in moderate to excellent yields. In this protocol the Ugi condensation of aromatic aldehydes, anilines, acids, and isocyanides leads to the formation of bis-amides in methanol at room temperature. This approach employed simple reaction conditions, including Ugi product as starting material, CuI, L-proline as a ligand, and cesium carbonate, in DMSO for 8 h. This method demonstrated efficiency in synthesizing fused-nitrogen-containing heterocycles through a convenient pathway.