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Selenium-Catalyzed Oxidative C–H Amination of (E)‑3-(Arylamino)-2-styrylquinazolin-4(3H)‑ones: A Metal-Free Synthesis of 1,2-Diarylpyrazolo[5,1‑b]quinazolin-9(1H)‑ones

Posted on 2019-02-11 - 00:00
A novel metal-free catalysis protocol for the synthesis of 1,2-diarylpyrazolo­[5,1-b]­quinazolin-9­(1H)-ones via intramolecular oxidative C–H amination of (E)-3-(arylamino)-2-styrylquinazolin-4­(3H)-ones has been developed in moderate to good yield. The method shows good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2,3-fused quinazolinones. Moreover, the present synthetic route can be readily scaled up to gram quantity without difficulty. A possible mechanism involves a seleniranium ion followed by three-membered ring opening to form the C–N bond.

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