G. Marzoni
Mar 1, 1986
Citations
0
Influential Citations
8
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
A two-reaction synthesis of 2-substituted-4-chloromethylthiazoles from thioamides and 1,3-dichloroacetone is reported. The first step, cyclization to a 2-substituted-4-chloromethyl-4-hydroxythiazoline is carried out in the presence of bicarbonate in an aprotic solvent. Dehydration of this intermediate to a 2-substituted-4-chloromethylthiazole is accomplished by reaction with thionyl chloride, sulfuryl chloride, phosphoryl chloride, phosphorus trichloride or phosphorus pentachloride. Substituents on the thioamide, such as amino, alkyl, or aryl, are shown not to affect the success of the reaction. As a trend, alkylthioamides give slightly better yields of 4-chloromethylthiazoles than do arylthioamides. The yields of 4-chloromethylthiazoles prepared using this procedure are comparable to the yields obtained using acid catalyzed procedures.