860346-40-3Relevant academic research and scientific papers
New quinoline-2, -3, and 4-yl-(amino) methylphosphonates: Synthesis and study on the C-P bond cleavage in quinoline-2 and -4 derivatives under acidic conditions
Michalska, Joanna,Boduszek, Bogdan,Olszewski, Tomasz K.
, p. 617 - 624 (2011/12/04)
Synthesis of new quinoline-(amino)methylphosphonic acids, their phosphonate esters, and phosphine oxides is presented. The desired new compounds were efficiently obtained by nucleophilic addition of phosphorous species to quinoline-derived Schiff bases. In addition, it was discovered that heating of quinolin-2 and quinolin-4-yl-(amino)-methylphosphonates with aqueous HCl leads to their decomposition resulting in a rupture of the C-P bond, rejecting of the phosphorus containing fragment, and formation of the corresponding secondary quinoline-2 and quinoline-4-alkylamines. Two alternative mechanistic pathways for this cleavage are postulated. Copyright
