1976 年 24 巻 5 号 p. 948-959
The reaction of 2-acylamino-3, 3-dichloroacrylonitriles (1) with various mercaptans in the presence of base gives 2-acylamino-3, 3-bis (substituted mercapto) acrylonitriles (5) or 2-acylamino-3-chloro-3-(substituted mercapto) acrylonitriles (17), each in good yield, depending upon the amount of mercaptans used. Similar nucleophilic substitutions are possible with the corresponding amides (8, 9), N-acylamides (10), esters (7), and acid (11). Treating the 3-mercapto acrylic acid derivatives thus obtained with silver compounds, such as Ag2O, Ag2CO3, and CH3COOAg, gives an excellent new method for synthesizing 5-(substituted mercapto) oxazoles (4). The scope and limitations of this new cyclization are also described.