First synthetic entry to the trimer stage of 5,6-dihydroxyindole polymerization: ortho-alkynylaniline-based access to the missing 2,7':2',7''-triindole.
5,6-Dihydroxyindole oligomers are valuable synthetic targets for the structural characterization of eumelanin biopolymers as well as for the realization of bioinspired functional materials. An ortho-alkynylaniline-based strategy allowed the first access to a trimer, the missing 5,5',5'',6,6',6''-hexaacetoxy-2,7':2',7''-triindole, and its detection as a minor intermediate en route from 5,6-dihydroxyindole to eumelanin-like polymers.
Capelli
Luigia
L
Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte S. Angelo, via Cintia 4, I-80126, Naples, Italy.
Manini
Paola
P
Pezzella
Alessandro
A
d'Ischia
Marco
M
D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D058105:Polymerization
D000814:Aniline Compounds; D007211:Indoles; C033871:5,6-dihydroxyindole