110700-77-1Relevant articles and documents
Chloromethyl Substituted Heterocycles from Methyl Chlorotetrolate
Janietz, D.,Goldmann, B.,Rudorf, W.-D.
, p. 607 - 616 (2007/10/02)
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-thiazolopyrimidin-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.