Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 5, Pages 2798-2807Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03179
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Funding
- National Natural Science Foundation of China [21572162]
- Natural Science Foundation of Zhejiang Province [LQ18B020006]
- Science and Technology Project of Zhejiang Province [2016C31022]
- Xinmiao Talent Planning Foundation of Zhejiang Province [2017R426046]
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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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