Notiz Untersuchungen zur 6‐Hydroxyindol‐Bildung bei der Nenitzescu‐Reaktion, I Nucleophile Addition an  N ‐Chinonyl‐enaminone | Zendy

Kuckländer Uwe | Zendy; Ulmer Petra | Zendy; Kuna Krystina | Zendy; Töberich Hildegard | Zendy

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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 .

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