100616-18-0Relevant academic research and scientific papers
α-dicarbonylmonoximes as nucleophiles and neighbour groups
M?hrle, Hans,Keller, Georg
, p. 632 - 642 (2007/10/03)
The α-dicarbonylmonooximes 1 and 11 do not react as simple "CH-acidic-compounds" in the Mannich condensation. In a concerted reaction with aminals in absolute dioxane they give rise to the products 4a - e and 12a - e with better practicability and much higher yields compared with the conventional method. The Mannich bases with a cyclic amine part show in the dehydrogenation, using mercury-EDTA, a neighbouring group participation of the oxime in type 4 and of the oxime or amide function in 12 yielding cyclized products. For the reaction a plausible mechanism is proposed.
