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Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2‑Aryl-3-(arylamino)­quinazolinones: Synthesis of Fluorescent Indazolo­[3,2‑b]­quinazolinones

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journal contribution
posted on 17.10.2014, 00:00 by Weiguang Yang, Jiuxi Chen, Xiaobo Huang, Jinchang Ding, Miaochang Liu, Huayue Wu
A palladium-catalyzed intramolecular aerobic oxidative C–H amination of 2-aryl-3-(arylamino)­quinazolinones has been developed, providing a variety of substituted indazolo­[3,2-b]­quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade “rollover” cyclometalation and C–H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.