Premium
Notiz Untersuchungen zur 6‐Hydroxyindol‐Bildung bei der Nenitzescu‐Reaktion, I Nucleophile Addition an N ‐Chinonyl‐enaminone
Author(s) -
Kuckländer Uwe,
Ulmer Petra,
Kuna Krystina,
Töberich Hildegard
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891220132
Subject(s) - chemistry , phenoxazine , hydroquinone , nucleophile , nucleophilic addition , medicinal chemistry , hydrolysis , stereochemistry , organic chemistry , catalysis , pharmacology , medicine , phenothiazine
Investigation on the Formation of 6‐Hydroxyindole in the Nenitzescu Reaction, I Nucleophilic Addition to N ‐Quinonlyenaminones 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 .