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Synthesis and Photochemical Behaviour of 2‐Amino‐1,3‐Cyclohexadienes
Author(s) -
Kilger Ralf,
Margaretha Paul
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660302
Subject(s) - chemistry , pyrrolidine , enamine , amine gas treating , enone , derivative (finance) , hydrolysis , medicinal chemistry , morpholino , nitrogen atom , organic chemistry , photochemistry , ring (chemistry) , catalysis , biochemistry , zebrafish , financial economics , economics , gene
The reaction of the 4,4‐dialkylated 2‐cyclohexenones 1 or 2 with a twofold excess of a secondary amine 3 affords the 2‐amino‐1,3‐cyclohexadienes 4 and 5 , respectively. Irradiation (λ ≧ 300 nm) of the morpholino derivative 4a yields a mixture of the isomeric 3‐morpholino‐6‐methyl‐1,3,5‐heptatrienes 6 and 7 , while 5 gives only one corresponding product 8 . The reaction of enone 1 with an equimolar amount of pyrrolidine ( 3c ) affords the bis ‐enamine 9 which is converted to the unsaturated diketone 10 by oxidative hydrolysis.