A facile and efficient procedure for the synthesis of substituted thiazole-2(3H)-thiones and thiazolidine-2-thiones by the reaction of primary amines, carbon disulfide, and nitroepoxides is described. By using secondary amines in this protocol, the corresponding dithiocarbamate-substituted phenyl-2-propanones were prepared in excellent yields. In addition, substituted thiazoles and 1-(alkylthio)-1-phenylpropan-2-ones were prepared in reactions of S-alkyl dithiocarbamates and nitroepoxides.
Nitroepoxides are easily transformed into benzodiazepines, tetrahydrobenzodiazepines, imidazopyridines, and N-alkyl tetrahydroquinoxalines by treatment with 2-aminobenzylamines, 2-aminopyridines, and N-alkyl 1,2-diaminobenzenes, respectively. Regioselectivity is controlled through attack of the most nucleophilic nitrogen of the unsymmetrical diamine to the β position of the epoxide. These reactions represent an efficient way to prepare privileged bioactive structures.
An environmentally benign procedure for the synthesis of 2‐(3‐alkyl‐4‐oxo‐2‐thioxo‐1,3‐thiazinan‐5‐yl)acetic acid via the one‐pot three‐component reaction of primary amines, carbon disulfide, and itaconic anhydride in water is described. Also, this protocol was expanded for the synthesis of succinic acids containing a dithiocarbamate group by using hindered primary amines and secondary amines.
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