134208-94-9Relevant academic research and scientific papers
Oxidation of Diethyl (Pyridylmethyl)malonates with Mn(III) Acetate, Ce(IV) Ammonium Nitrate, and Iron(III) Perchlorate in the Presence of Alkenes and Alkynes
Citterio, Attilio,Sebastiano, Roberto,Carvayal, Magaly Caceres
, p. 5335 - 5341 (2007/10/02)
The oxidation of substituted diethyl 2-,3-, or 4-picolylmalonates (1a-g) by Mn(III) acetate in acetic acid, Ce(IV) ammonium nitrate in methanol, and Fe(III) perchlorate in acetonitrile in the presence of substituted alkenes (2) and alkynes (3) affords substituted tetra- or dihydroquinolines and/or isoquinolines (4-9) in good to excellent yield.The influence of reaction medium on yield and isomer distribution has been investigated.A mechanism involving oxidative deprotonation of malonic esters by high-valent metal salts to malonyl radicals, their addition to olefins, and intramolecular homolytic substitution to protonated or metal-complexed heteroaromatic bases by the resulting substituted carbon radicals is suggested.
