Aminophthalimide as a Protected Nitrogen Source for N-Insertion to Indenones
1Department of Gastrointestinal Oncology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430072, China.
Abstract:
Nitrogen scanning is central to medicinal chemistry, yet N-positional variants and N-H analogues often require de novo synthesis. We report a nitrene-based, two-step one-pot formal N-H insertion into indenones to access isoquinolinones. N-Aminophthalimide, activated by PIDA, aziridinates the C═C bond and the resulting N-NPhth intermediate undergoes acid-promoted rearrangement in one pot. The method tolerates diverse substrates, including previously unreactive 2-alkyl and strongly electron-poor enones, and enables easy deprotection to N-H isoquinolinones.
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