1982 年 40 巻 2 号 p. 123-135
The characteristic reaction of Schiff bases and a variety of related compounds with carbon disulfide leading to N-substituted β-imino-dithiocarboxylic acids or the related derivatives was investigated especially by R. Mayer, R. Gompper, and their co-workers. The reaction of ketimines having no substituent on the nitrogen atom, however, had not been explored until 1966 when we started the title investigation.
We outline here the essentials of our investigation originated in the synthesis of N-unsubstituted, β-imino-dithiocarboxylic acids. Our finding was that the syntesis required no isolations of ketimines ; the reaction of ketones with carbon disulfide in the presence of aqueous ammonia alone sufficed. Special mention may be made of stereochemical relationships in the syntheses and reactions of the acids, involving a novel mode of ring opening in the synthesis from 2-methylcyclopentanone. Synthetic applications are described together with a variety of new type compounds obtained. In addition, we referred to the reaction of acid amide-type compounds with carbon disulfide.
Finally, we touched on some of our future projects, and, further, potentiality of powerful chemotherapeutic agents in this area.