Copper-Catalyzed Sequential Ullmann N-Arylation and Aerobic Oxidative C–H Amination: A Convenient Route to Indolo[1,2-c]quinazoline Derivatives

Abstract

An efficient synthesis of indolo[1,2-c]quinazoline derivatives has been developed by copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination. The protocol uses readily available 2-(2-halophenyl)-1H-indoles and (aryl)methanamines as the starting materials to afford indolo[1,2-c]quinazolines, which are the core units of hinckdentine A.

Quinazoline derivatives: synthesis and bioactivities

“…It raised attention from many chemists and became one of the focal point in organic chemistry research in recent years. Sang et al reported a copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination for the convenient synthesis of indolo[1,2-c]quinazoline derivatives [41]. In their research, 2-(2-halophenyl)-1H-indoles and (aryl)methanamines were adopted as raw materials to generate corresponding Schiff base via Ullmann reaction.…”

Synthesis of 6‐Aminoindolo[2,1‐a]isoquinoline‐5‐carbonitriles by the Cu‐Catalyzed Reaction of 2‐(2‐Bromophenyl)‐1H‐indoles with CH2(CN)2

“…): Thermo Scientific Exactive spectrometer; in m/z. [4], and 2-(2-bromophenyl)-5-chloro-1H-indole (1g) [4] were prepared according to reported procedures. All other chemicals used in this study were commercially available.…”

“…It should be noted that, during our work, we became aware of a report on the elaboration of these 1H-indole derivatives to the synthesis of indolo[2,1-c]quinazolines by Zhang and co-workers. [4].…”

Synthesis and Biological Evaluation of Some Quinazoline Heterocyclic Derivatives

“…A convenient and clean water-mediated synthesis of a series of indolo[1,2-c] quinazoline derivatives was reported using alternative nonconventional energy sources. The products are obtained in shorter times with excellent yields (78-89 %) from the MCR of 2-aminobenzimidazole, malononitrile, and carbonyl compounds [55]. In their research, 2-(2-halophenyl)-1H-indoles and (aryl)methanamines were adopted as raw materials to generate corresponding Schiff base via the Ullmann reaction.…”