Application of ynamides in the synthesis of 2-amidoindoles.
A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-iodoanilines is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without activation of the alkyne.
Dooleweerdt
Karin
K
Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Ruhland
Thomas
T
Skrydstrup
Troels
T
D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D000577:Amides; D000814:Aniline Compounds; D007211:Indoles; D008024:Ligands; D010165:Palladium; C075715:3-iodoaniline