Synthesis of 2-Aryl-Substituted Indole-3-acetic Acid Derivatives via Intramolecular Imino-Stetter Reaction of Aldimines with Cyanide
- Authors
- Lee, Seong Jong; Seo, Hong-Ahn; Cheon, Cheol-Hong
- Issue Date
- 19-5월-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- aldimines; 2-arylindole-3-acetic acid derivatives; cyanide; imino-Stetter reaction; umpolung
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.358, no.10, pp.1566 - 1570
- Indexed
- SCIE
SCOPUS
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 358
- Number
- 10
- Start Page
- 1566
- End Page
- 1570
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/88632
- DOI
- 10.1002/adsc.201600155
- ISSN
- 1615-4150
- Abstract
- A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino-Stetter reaction of aldimines obtained from 2-aminocinnamic acid derivatives and aromatic aldehydes with cyanide, affording 2-aryl-substituted indole-3-acetic acid derivatives. Furthermore, the usefulness of this method was successfully demonstrated by the synthesis of an FPTase inhibitor, one of the biologically important 2-arylindole-3-acetic acid derivatives.
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