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Reaction of 1,6‐Dioxo‐2,4‐Diene with Aziridine and Secondary Amine
Author(s) -
Sun TsungHsien,
Ong ChiWi
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700225
Subject(s) - chemistry , diene , aziridine , enone , intramolecular force , nucleophile , enol , aldol reaction , adduct , isomerization , medicinal chemistry , ketone , amine gas treating , aldol condensation , photochemistry , ring (chemistry) , stereochemistry , organic chemistry , catalysis , natural rubber
The (2 E ,4 E )‐ and (2 E ,4 Z )‐1‐phenyl‐1,6‐dioxo‐hepta‐2,4‐diene reacts with aziridine to give aziridinecyclopentenol 3. This product arises from an intermolecular Michael addition of a nitrogen lone pair to the less reactive enone, followed by an intramolecular aldol reaction of the enol with ketone. Furthermore, the initially formed enol did not undergo nucleophilic attack onto the aziridine ring to form heterocycles. Interestingly, the reaction with secondary amine did not give the cyclopentenol adduct, and this only leads to the isomerization of (2 E ,4 Z )‐1‐phenyl‐1,6‐dioxo‐hepta‐2,4‐diene to the more stable (2 E ,4 E) ‐1‐phenyl‐1,6‐dioxo‐hepta‐2,4‐diene by addition to the more reactive enone.