Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue 11, Pages 3005-3014Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202100588
Keywords
annulation; C-H functionalization; cinnoline; rhodium; vinylene carbonate
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIT) [2019R1A4A2001451, 2020R1A2C3005357, 2020R1I1A1A01052800]
- National Research Foundation of Korea [2019R1A4A2001451, 2020R1A2C3005357, 2020R1I1A1A01052800] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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The Rh(III)-catalyzed C-H annulation reactions provide a rapid access to indazolocinnolines and phthalazinocinnolines, which are important assets for developing novel bioactive compounds. Intriguingly, a vinylene carbonate acts as a vinyl transfer agent enabling the [4+2] annulation reaction, characterized by simplicity, mild reaction conditions, and broad functional group tolerance.
The Rh(III)-catalyzed C-H annulation reactions of N-aryl indazolones or N-aryl phthalazinones with a vinylene carbonate is described herein. This transformation provides the rapid access to indazolocinnolines and phthalazinocinnolines as important assets towards the development of novel bioactive compounds. Intriguingly, a vinylene carbonate acts as a vinyl transfer agent to enable the [4+2] annulation reaction. This method is characterized by its simplicity, mild reaction conditions, and broad functional group tolerance.
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