Abstract
1. The seven-membered heterocyclic compounds methyl 6-(acylamino)-2,2-dimethyl-5-oxo-1-thia-4-azacycloheptane-3-carboxylates were synthesized by the condensation of 3-mercaptovaline (3,3-dimethylcysteine) methyl ester with 2-(acylamino)acrylic acids, and by successive halogenation and dehydrohalogenation reactions these products were converted into new isomers of phenyl- and benzyl-penicillin: 2-(acylamino)-2,2-dimethyl-5 -oxo-1 -thia -5-aza-5-cycloheptene-3 -carboxylic acids. 2. It was shown that the isomerization of six-membered cyclic compounds into unsaturated seven-membered cyclic compounds can occur, the case studied being that of the conversion of methyl 6-(acylamino)-6-(halomethyl)-2,2-dimethyl-5-oxo-3-thiarnorpholinecarboxylates (XII) into methyl 6-(acylamino)-2,2-dimethyl -5 -oxo-1 -thia -4-aza-5-cycloheptene-3 -carboxylates (VII).
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