The reaction of anthranilonitrile and triethylorthoformate revisited: formation of dimeric and trimeric species

The reaction of anthranilonitrile and triethylorthoformate was performed under different experimental conditions, leading to substituted quinazolines, triazachrysenes or quinazolinyl-aminophenyl quinazolines. A mechanistic proposal is presented to rationalize the formation of these compounds. The fluorescence properties of the highly conjugated triazachrysene structures were studied and the fluorescence quantum yield for compounds 5 and 13 was comparable to that of pyrene.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide