CHLORINE DISPLACEMENT OF HETEROCYCLIC HALIDES BY ENOLATE-OXYGEN - SYNTHESIS OF 1,3-OXATHIOL-2-IMINES FROM 5-CHLORO-1,2,4-THIADIAZOL-3(2H)-ONES AND ACTIVE METHYLENE KETONES AND ESTERS
G. Labbe et al., CHLORINE DISPLACEMENT OF HETEROCYCLIC HALIDES BY ENOLATE-OXYGEN - SYNTHESIS OF 1,3-OXATHIOL-2-IMINES FROM 5-CHLORO-1,2,4-THIADIAZOL-3(2H)-ONES AND ACTIVE METHYLENE KETONES AND ESTERS, Journal of the Chemical Society. Perkin transactions. I, (10), 1994, pp. 1263-1265
1,3-Oxathiol-2-imines 4-8 are conveniently prepared from 5-chloro-1,2,
4-thiadiazol-3(2H)-one 3 and pentane-2,4-dione, methyl acetoacetate, d
imethyl malonate and cyclohexane-1,3 diones, while the normal substitu
tion product 9 is obtained from the thiadiazole 3 and Meldrum's acid.