95395-19-0Relevant academic research and scientific papers
AROYLACETYLATION OF AMIDES BY 6-ARYL-2,2-DIMETHYL-1,3-DIOXIN-4-ONES
Andreichikov, Yu. S.,Vinokurova, O. V.,Gein, V. L.
, p. 2189 - 2192 (2007/10/02)
Aroylketenes, generated during the thermolysis of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones, react with formamide, acetamide, and anthranilamide with the formation of N-acylaroylacetamides.The N-(ethoxycarbonyl)aroylacetamides formed during the aroylacetylation of urethane undergo cyclization at 185-190 deg C to 6-aryl-3,4-dihydro-2H-1,3-oxazine-2,4-diones.
Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H,4H-1,3-dioxin-4-ones
Sato, Masayuki,Ogasawara, Hiromichi,Komatsu, Sachiko,Kato, Tetsuzo
, p. 3848 - 3856 (2007/10/02)
Thermal reaction of 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones (1) with amines was studied.Acylketenes 2, generated by heating of 1, reacted with anilines and benzylamine to give the corresponding β-ketocarboxamides (3,4, and 5) in good yields.The reaction of 1 with ammonia gave 3-amino-2-alkenamides (7), which were hydrolyzed to β-ketocarboxamides (6).The former products 7 were readily transformed to the 6-substituted 2-methyl-3H-pyrimidin-4-ones (9) via the 3-acetamido-2-alkenamides (8).Acylation of O-benzylhydroxylamine with 1 gave the β-ketohydroxamic acids 10.Debenzylation of 10 followed by cyclization gave rise to 5-alkyl-3-hydroxyisoxazoles (12).The reaction of 1 with amides gave the corresponding N-acetylated amides (13). Keywords --- 2H,4H-1,3-dioxin-4-one; thermal fragmentation; acylketene; acylation; carboxamide; hydroxamic acid; 3-hydroxyisoxazole; 3H-pyrimidin-4-one
