Synthesis of (2H)-Indazoles and Dihydrocinnolinones through Annulation of Azobenzenes with Vinylene Carbonate under Rh(III) Catalysis
- Authors
- Park, Min Seo; Moon, Kyeongwon; Oh, Harin; Lee, Ji Yoon; Ghosh, Prithwish; Kang, Ju Young; Park, Jung Su; Mishra, Neeraj Kumar; Kim, In Su
- Issue Date
- Jul-2021
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.23, no.14, pp 5518 - 5522
- Pages
- 5
- Journal Title
- ORGANIC LETTERS
- Volume
- 23
- Number
- 14
- Start Page
- 5518
- End Page
- 5522
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/146501
- DOI
- 10.1021/acs.orglett.1c01866
- ISSN
- 1523-7060
1523-7052
- Abstract
- The Rh(III)-catalyzed C-H functionalization and subsequent intramolecular cyclization between azobenzenes and vinylene carbonate is described herein. Depending on the electronic property of azobenzenes, this transformation results in the formation of (2H)-indazoles or dihydrocinnolin-4-ones through the generation of ortho-alkylated azo-intermediates followed by decarboxylation. Surprisingly, vinylene carbonate acts as an acetaldehyde or acetyl surrogate to enable the [4 + 1] or [4 + 2] annulation reaction. This transformation is characterized by its mild reaction conditions, simplicity, and excellent functional group compatibility.
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