Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds.
A unified convenient strategy for the synthesis of 5,6-dihydroxyindole-derived 2,7'-, 2,2'-, and 2,3'-biindolyls is reported, which is based on proper manipulation of key o-ethynylaniline precursors. By the same methodology 5,6-diacetoxy-7-iodoindole can also be obtained in good yield.
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
Napolitano
Alessandra
A
d'Ischia
Marco
M
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D003500:Cyclization; D019281:Dimerization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008543:Melanins / Q000737:chemistry*; D008956:Models, Chemical; D010084:Oxidation-Reduction
C483919:2-ethynylaniline; C545901:5,6-diacetoxy-7-iodoindole; D000814:Aniline Compounds; D004791:Enzyme Inhibitors; D007211:Indoles; D008543:Melanins; C041877:eumelanin; D000114:Acetylene; C033871:5,6-dihydroxyindole