22903-00-0Relevant articles and documents
Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging
Amarante, Giovanni W.,Carvalho, Bernardo B. P. P.,Correa, José R.,Franco, Chris H. J.,Meirelles, Luan V.,Neto, Brenno A. D.,Passos, Saulo T. A.,de Castro, Pedro P.
, (2022/02/16)
A transition metal-free protocol for the preparation of fluorescent and non-fluoresent 3-methylthio-4-arylmaleimides in a single step through a new rearrangement from thiazolidine-2,4-diones is described. By employing the optimized reaction conditions, a broad scope of derivatives was prepared in ≤97% yield. The reaction tolerated several substituted aryl groups, including the challenging preparation of pyridyl-containing derivatives. A series of control experiments strongly suggested that the new rearrangement involves a key isocyanate intermediate and a further reaction with in situ-generated methylthiomethyl acetate. The photophysical properties of some of the synthesized derivatives as well as their use in live cell imaging were also investigated, revealing that some of the substituted maleimides are capable of selectively staining different regions of the cells.
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.
