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Synthesis of Cinnolines via Rh(III)-Catalyzed Annulation of N-Aryl Heterocycles with Vinylene Carbonate

Authors
Kim, S[Kim, Suho]Choi, SB[Choi, Su Bin]Kang, JY[Kang, Ju Young]An, W[An, Won]Lee, SH[Lee, Suk Hun]Oh, H[Oh, Harin]Ghosh, P[Ghosh, Prithwish]Mishra, NK[Mishra, Neeraj Kumar]Kim, IS[Kim, In Su]
Issue Date
Nov-2021
Publisher
WILEY-V C H VERLAG GMBH
Keywords
annulation; C-H functionalization; cinnoline; rhodium; vinylene carbonate
Citation
ASIAN JOURNAL OF ORGANIC CHEMISTRY, v.10, no.11, pp.3005 - 3014
Indexed
SCIE
SCOPUS
Journal Title
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume
10
Number
11
Start Page
3005
End Page
3014
URI
https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/90719
DOI
10.1002/ajoc.202100588
ISSN
2193-5807
Abstract
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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