D. Janietz, B. Goldmann, W. Rudorf
1988
Citations
0
Influential Citations
7
Citations
Journal
Journal Fur Praktische Chemie-chemiker-zeitung
Abstract
Chloromethyl Substituted Heterocycles from Methyl Chlorotetrolate Reaction of amidines, isothioureas or thioureas with methyl chlorotetrolate 1 leads to pyrimidin-4-ones 2 and 1,3-thiazines (3), respectively. Compounds 2 and 3 are starting materials for the synthesis of 6-chloromethyl-uracils (4), 1,3-thiazine-2,4-dione 5 and 6-benzylthiomethyl-thiazinone (6). 2-Aminothiazoles react with the ester 1 to yield 5-chloromethyl-thiazolo[3,2-a]pyrimidin-7-ones (7). The 5-oxo isomers 8 are obtained by reaction of thiazoles with ethyl γ-chloroacetoacetate. By reaction of 2-mercaptoimidazoles and 1 or chlorotetrolic acid the condensed 1,3-thiazinones (10) result. In the latter case the intermediate 9 is isolated. It can be cyclised to 10 by heating with acetic anhydride and sulphuric acid.