The chemistry of 5-oxodihydroisoxazoles. Part 19.1 The synthesis and photolysis of N-thioacylisoxazol-5(2H)-ones

Abstract

5-Oxodihydroisoxazoles react with thiocarbonyl chlorides to afford N-thioacylisoxazol-5(2H)-ones which lose carbon dioxide under photochemical conditions and undergo intramolecular cyclisation of the iminocarbene to afford thiazoles. However, in some cases loss of carbon dioxide is accompanied by loss of sulfur, giving 1,3-oxazin-6-ones.