J. Michalska, B. Boduszek, T. Olszewski
Sep 1, 2011
Citations
0
Influential Citations
27
Citations
Journal
Heteroatom Chemistry
Abstract
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 CP 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. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:617–624, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20704