The indoleacetic acids in IMCRs: a three-component Ugi reaction involving TosMIC

Isocyanide-based MCRs (IMCRs) involving for the first time the biological and pharmaceutical active indoleacetic acids are studied. In particular, the catalytic behavior of 2-acetyl-indoleacetic acid in the Ugi three-component reaction with TosMIC is emphasized. The reaction was optimized, revealing...

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Bibliographic Details
Published in:Tetrahedron 2016-08, Vol.72 (33), p.5149-5156
Main Authors: Neochoritis, Constantinos G., Livadiotou, Despina, Tsiaras, Vassilios, Zarganes-Tzitzikas, Tryfon, Samatidou, Evanthia
Format: Article
Language:English
Subjects:
Indoleacetic acid
Multi-component reactions
Passerini reaction
TosMIC
Ugi reaction
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Summary:Isocyanide-based MCRs (IMCRs) involving for the first time the biological and pharmaceutical active indoleacetic acids are studied. In particular, the catalytic behavior of 2-acetyl-indoleacetic acid in the Ugi three-component reaction with TosMIC is emphasized. The reaction was optimized, revealing the catalytic role of aromatic carboxylic acids as well, yielding a small library of a-aminoamides. Full assignment of all 1H and 13C NMR chemical shifts has been unambiguously achieved. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.07.013