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Zur Umsetzung von 2‐Amino‐2‐cyclopenten‐1‐on‐Derivaten mit p ‐Benzochinonen, II
Author(s) -
Kuckländer Uwe,
Schneider Bettina
Publication year - 1988
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.19881210331
Subject(s) - chemistry , quinone , hydroquinone , adduct , medicinal chemistry , benzoquinone , yield (engineering) , acetylation , 1,4 benzoquinone , stereochemistry , organic chemistry , biochemistry , materials science , metallurgy , gene
Reaction of 2‐Amino‐2‐cyclopenten‐1‐one Derivatives with p ‐Benzoquinones, II N ‐Aryl‐α‐ketoenamine 2a reacts with methyl‐ p ‐benzoquinone 1a to yield the hydroquinone adduct 3a . This is oxidized to the stable quinone 5a , which is cyclisized to indolequinone 4 and the quinonoid heterocyclus 6a . Compounds 6a and 4 are reduced and acetylated to hydroquinones 9a and 7 , respectively. The path of the reaction is discussed. Reaction of 1b and 2b yields directly quinone 6b .