117527-10-3Relevant articles and documents
Investigations on the Formation of 6-Hydroxyindole in the Nenitzescu Reaction, I. - Nucleophilic Addition to N-Quinonyl-enaminones
Kucklaender, Uwe,Ulmer, Petra,Kuna, Krystina,Toeberich, Hildegard
, p. 209 - 212 (2007/10/02)
N-Quinonyl-enaminone 6 is synthesized.Its transformation into 6-hydroxyindole 5 fails.Thus, structure 6 is no intermediate in the formation of 5 from 1 and 2.Nucleophilic attack of trifluoroacetate on enaminone 6 yields hydroquinone 9a, which is hydrolysed to 10a,b.The structures of 9a and 10a,b are proven spectroscopically and by oxidation of 10b to 11, being equilibrated with phenoxazine 12.The latter is reduced to 13a,b. - Keywords: Nenitzescu reaction / Phenoxazine derivatives / Ring-chain tautomerism / Enaminone protonation