New 4-trifluoromethyl-1,3-oxazin-6-ones have been prepared in excellent yields from 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.
Janousek, Advances in Organic Chemistry”, 9 (1976)
Norris, J. Org. Chem., 27, 1449 (1962)
Swarts, Bull. Acad. Sci. Belg., 5, 680 (1926)
Bibliographic reference
Decockplancquaert, MA. ; Evariste, F. ; Guillot, N. ; Janousek, Z. ; Maliverney, C. ; et. al. Syntheses of New 4-trifluoromethylated 1,3-oxazin-6-ones From the Enamine of Ethyl Trifluoroacetoacetate. In: Societes Chimiques Belges. Bulletin, Vol. 101, no. 4, p. 313-321 (1992)