141860-83-5Relevant 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 (1998)
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.
SYNTHESES OF NEW 4-TRIFLUOROMETHYLATED 1,3-OXAZIN-6-ONES FROM THE ENAMINE OF ETHYL TRIFLUOROACETOACETATE
Decock-Plancquaert, Marie-Aimee,Evariste, Francois,Guillot, Nadine,Janousek, Zdenek,Maliverney, Christian,et al.
, p. 313 - 322 (2007/10/02)
New 4-trifluoromethyl-1,3-oxazin-6-ones have been prepared in excellent yields form ethyl 3-amino-4,4,4-trifluorocrotonate (ATFC) by two original procedures: reaction of ATFC with phosgeniminium chlorides to give 2-dialkylamino-4-trifluoromethyl-1,3-oxazin-6-ones, or action of chlorinating agents on N-acyl ATFC.The reactivity of ATFC in these reactions is compared with non-fluorinated analogs.
