Sourav Ghorai
UIC
New reactivity of arynes was explored under silver-catalysed conditions wherein arynes were generated from tri- and tetraynes through the hexahydro Diels-Alder reaction at elevated temperature. Trapping of arynes with nitrile forms nitrilium ion intermediate, which reacts with water or carboxylic acid to afford amides or imides, respectively. In the absence of other nucleophilic species, the nitrlium ion intermediate reacts further with another molecule of nitrile to furnish quinazoline derivatives. In this silver-catalysed protocol, the unconventional reactivity of arynes has been manifested such that even weekly nucleophilic nitriles can participate in the aryne-mediated reaction to produce a large array of functionalized aromatic compounds in moderate to high yield.