Synthesis of 2-Vinylindole-3-Acetic Acid Derivatives via Cyanide-Catalyzed Imino-Stetter Reaction
- Authors
- Seo, Hong-Ahn; Cheon, Cheol-Hong
- Issue Date
- 2-9월-2016
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.81, no.17, pp.7917 - 7923
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 81
- Number
- 17
- Start Page
- 7917
- End Page
- 7923
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/87545
- DOI
- 10.1021/acs.joc.6b01621
- ISSN
- 0022-3263
- Abstract
- A new method for the synthesis of 2-vinyl-indole-3-acetic acid derivatives from aldimines, which are derived from 2-aminocinnamic acid derivatives and alpha,beta-unsaturated aldehydes, via a cyanide-catalyzed imino-Stetter reaction is described. Various types of 2-aminocinnamic acid derivatives and alpha,beta-unsaturated aldehydes could be used in this protocol, and the desired 2-vinyl substituted indole-3-acetic acid derivatives were obtained in high yields. This cyanide-catalyzed imino-Stetter reaction was further extended to the preparation of indole-3-acetic acid derivatives bearing a carboxylic acid functionality at the 2-position, using aldimines obtained from glyoxylates and 2-aminocinnamic acid derivatives.
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