Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 53, Issue 23, Pages 9244-9248Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf051712h
Keywords
cysteine conjugates; Michael addition; alpha,beta-unsaturated alclehydes; hexahydro-1,4-thiazepine; 1,4-thiazepane; 3-methyl-2-butenal; 3-methyl-2-hexenal; citral
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The reaction of beta,beta-disubstituted acroleins [3-methyl-2-butenal (1), 3-methyl-2-hexenal (2), and citral (3)] with cysteine gave 1:2 adducts of a novel structural type, namely hexahydro-1,4-thiazepines. To the best of our knowledge, the spontaneous formation of a seven-membered heterocycle from the addition of cysteine to a,p-unsaturated aldehydes is unprecedented. The adduct 6 obtained from citral, under acidic conditions, reacted further to give the new bicyclic compound 8.
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