49601-28-7Relevant articles and documents
Synthesis of 3-methylthio-4-aryl-3-pyrroline-2,5-diones and 3-arylpyrolidine-2,5-diones by reaction of nitroketene dithioacetal with arylacetonitriles
Shigemitsu, Yasuhiro,Tominaga, Yoshinori
, p. 2257 - 2260 (2007/10/03)
The reaction of nitroketene dithioacetal (1a), i.e., 2,2-bis(methylthio)-1-nitroethylene, with arylacetonitriles (2a-I) in the presence of the base like sodium hydroxide gave 4-nitrobut-2-enenitriles (3a-I) which were convened into 5-hydroxyimino-4-methylthio-3-phenyl-3-pyrrolin-2-ones (4a-i) under refluxing in methanol. Title compounds (5a-i) were readily obtained by the treatment of 4a-i with hydrochloric acid and were finally led to N-methylated products (6a-I) with methyl iodide. The reduction of maleimides (4 - 6) with zinc dust in acetic acid afforded the corresponding 3-arylpyrrolidine-2,5-diones (7a-i) that can be convened to pharmacologycally active compounds like mesembrines.