On the Reactivity of Penicillamine and its Derivatives. Joint Reaction of Elementary Sulfur and Gaseous Ammonia with Ketones, 97

Article abstract of DOI:10.1007/BF00809375

DL-penicillamine-hydrochloride was condensed with various aldehydes (1 - 22) and ketones (23 - 28) to the corresponding 5,5-dimethyl-thiazolidine-4-carboxylic acid hydrochlorides and the free bases respectively.Their methylesters were obtained with diazomethane or methanol (29 - 35).Various 5,5-dimethyl-thiazolidine-4-carboxylic acids were formylated in position 3 (36 - 39).The reactivity of the carboxylic group was studied for 3-formyl-2,2,5,5-tetramethyl-thiazolidine-4-carboxylic acid.Substituted N-penicillaminamides were obtained for the first time (40 - 53).Also some S-alkylated penicillamines were prepared (54 - 60).By diazotation of 2,2,5,5-tetramethyl-thiazolidine-4-carbonamide or of penicillaminamide itself, 2-carbamyl-3,3-dimethyl-ethylene-sulfide was obatined. - Keywords: 3-Formyl-2,2,5,5-tetramethyl-thiazolidine-carboxylic acid amides; N-Formyl-5,5-dimethyl-thiazolidine-4-carboxylic acids; S-Alkylpenicillamines