The Facile Isomerization of 4-Methylene-2-oxazolidinones to 4-Methyl-4-oxazolin-2-ones

Attempted synthesis of a keto diazene: reactions of propargylic amines, sulfamides, and ureas

“…2-Methyl-4-oxo-2-pentylacetamide (14). To 7.15 g (0.174 mol) of acetonitrile, 20 mL of concentrated H2S04, and 40 mL of glacial acetic acid was added 13.5 g (0.116 mol) of diacetone alcohol (4methyl-4-hydroxy-2-pentanone, Aldrich).…”

“…The dried CHC13 extract (MgS04) was concentrated to give an orange-red liquid. Distillation gave a yellow liquid (bp 115-118 0C/~1 mm) which crystallized from pentane at -78 °C to give 9.1 g (50%) of amide 14 which was recrystallized from pentane to give pure 2-methyl-4-oxo-2-pentylacetamide ( 14): mp 44-45 °C (lit. 46 °C);17 NMR (CDCls) 1.42 (s, 6 ), 1.96 (s, 3 ), 2.18 (s, 3 H) and 3.0 ppm (s, 2 H); IR (CHCI3) 3440,1746,1710, and 1658 cm"1.…”

Synthesis and Herbicidal Activities of 4-Substituted 3-Aryl-5-tert-butyl-4-oxazolin-2-ones

“…McCombie and coworkers reported the synthesis of 4-oxazolin-2-ones from R-aminoketones and ethyl chloroformate (McCombie and Parkes, 1912;Pain and Slack, 1951). Stoffel and co-workers described the synthesis of 4-oxazolin-2-ones from propargyl alcohol and phenyl isocyanate (Stoffel and Dixon, 1964;Sisido et al, 1962;Cum et al, 1968). Previously, in the course of the study of isoxazole compounds, we discovered a novel synthetic method for 4-oxazolin-2-ones (4) from acyl Meldrum's acids (1) and N-hydroxyaniline derivatives (2) via N-arylhydroxamic acids (3) as shown in Figure 1 (Sato et al, 1986).…”