197582-19-7Relevant academic research and scientific papers
The chemistry of 5-oxodihydroisoxazoles. Part 22. The synthesis of 1,3-oxazin-6-ones from N-thioacylisoxazol-5(2H)-ones
Millan, David S.,Prager, Rolf H.
, p. 3245 - 3252 (2007/10/03)
N-Thioacylisoxazol-5(2H)-ones, prepared by the reaction of thiocarbonyl chlorides with isoxazol-5(2H)-ones in the presence of base, are reduced by triphenylphosphine to afford 1,3-oxazin-6-ones and triphenylphosphine sulfide. If the thioacylation is carried out with phenyl chlorodithioformate, the thermal rearrangement of the intermediate, to again form the oxazin-6-one and sulfur, is so rapid that the use of the phosphine is not required. The presence of an ethoxycarbonyl group at C-3, or of a bromine atom at C-4 of the isoxazolone results in the formation of thiazoles.
The chemistry of 5-oxodihydroisoxazoles. Part 19. The synthesis and photolysis of N-thioacylisoxazol-5(2H)-ones
Prager, Rolf H.,Taylor, Max R.,Williams, Craig M.
, p. 2673 - 2678 (2007/10/03)
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. Copyright 1997 by the Royal Society of Chemistry.
