42520-13-8Relevant academic research and scientific papers
Reaction of Diketene-Acetone Adduct with Enamines, Ketene Acetals, Vinyl Ethers, and β-Diketones
Sato, Masayuki,Ogasawara, Hiromischi,Kato, Keiko,Sakai, Masako,Kato, Tetsuzo
, p. 4300 - 4305 (2007/10/02)
Diketene-acetone adduct (1) generates acetylketene (2) under heating.In order to compare the reactivity of 2 with that of diketene, the reaction of 1 with electron-rich olefins was investigated.On heating with 1 primary enamines (3a-d) produced the corresponding 3-substituted 2,6-dimethyl-4(1H)-pyridones (4a-d), while the tertiary enamine 3e gave the 4-pyrone derivative (7).The reaction of 1 with ketene acetals (8) gave the 2,2-diethoxy-2,3-dihydro-4-pyrone derivatives (9).The vinyl ether derivatives 13 similarly reacted with 1 to give the 4-pyrone derivative 15 or 16 as the major product.The result shows that both diketene and 2 react with electron-rich olefins in a similar manner.Keywords -- diketene; acetylketene; diketene-acetone adduct; enamine; ketene acetal; vinyl ether; 1,3-dioxin-4-one; 4-pyridone; 4-pyrone; cycloaddition
