Ruthenium‐Catalyzed Synthesis of Quinazolinones through Hydrogen Transfer and Cyclization

Abstract

An efficient ruthenium‐catalyzed tandem cyclization for the formation of C–N bond was developed by using hydrogen transfer reaction and intramolecular cyclization. This process relied on the efficient availability of nitroarenes and primary alcohols to form C–N bond by hydrogen transfer reaction. This method could be widely used in the synthesis of quinazolinone skeletons due to less waste, higher reaction efficiency and better functional groups tolerance. A series of quinazolin‐4(3H)‐ones derivatives were obtained with high production by using nitroarenes and primary alcohols as the substrates. Finally, based on the experimental results, a reasonable series reaction mechanism was proposed.

Fast quinazolinone synthesis by combining enzymatic catalysis and photocatalysis

“…The classical method for the synthesis of quinazolinones involves the condensation reaction between 2-aminobenzamide and aldehyde in the presence of various catalysts [17,18], including acids [19,20] and metal catalysts [21]. However, such reactions commonly require toxic solvents [22,23] or high temperature [24][25][26]. Therefore, organic chemists have sought to develop green and efficient approaches to synthesize quinazolinones.…”

Unexpected Insertion of Nitrogen into a C–C Bond: Access to 2,3-Disubstituted Quinazolinone Scaffolds

“…Alper and Wu described palladium-catalyzed cyclocarbonylation to give 2,3-disubstituted quinazolinones . Deng and Chu developed the hydrogen transfer reaction of N-substituted o -nitrobenzamides with benzylic alcohols under iron or ruthenium catalysis . Chiba and co-workers described transition metal free access to 2,3-disubstituted quinazolinones utilizing 5-aryl-4,5-dihydro-1,2,4-oxadiazoles in the presence of O 2 .…”