engleski

NMR Characterization of Quinoline-based Aminophosphonate Derivatives

Aminophosphonic acids and their esters have attracted continuous attention because of their wide range biological properties and potential applications in the pharmacological and agrochemical fields [1]. These organophosphorus compounds are also known as good complexing agents for various transition metals, of which platinum group metals form complexes with noticeable antitumor activity [2]. One of the simplest synthetic routes to alpha-aminophosphonates is the Kabachnik-Fields reaction, a three-component one-pot reaction of amine, carbonyl compound (aldehyde or ketone) and hydrophosphoryl compound [3]. Recently, we focused our attention on the influence of microwave irradiation on the Kabachnik-Fields synthesis of quinoline-based alpha-aminophosphonates [4]. In studied reactions with 3-quinoline derivatives, along with main products diethyl phosphonates (1, 4), unusual monoester phosphonate derivatives (2, 3, 5) were isolated. We present here the NMR characterization of compounds 1-5 using various one- and two-dimensional 1H, 13C and 31P NMR spectroscopic methods. [1] P. Kafarski, B. Lejczak, in Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity ; V.P. Kukhar, H.R. Hudson (Eds.) ; John Wiley & Sons: Chichester, 2000 ; pp 407-442. [2] Lj. Tušek-Božić, V. Cmrečki, J. Balzarini, E. De Clercq, Lett. Drug Des. Discovery 3 (2006) 528-533 ; and references cited therein. [3] R.A. Cherkasov, V.I. Galkin, Russ. Chem. Rev. 67 (1998) 857-882. [4] Lj. Tušek-Božić, M. Juribašić, M. Komac, V. Cmrečki, I. Zrinski, J. Balzarini, E. De Clercq, Lett. Org. Chem. 4 (2007) 332-338.

NMR spectroscopy; aminophosphonates; quinoline; Kabachnik-Fields reaction

nije evidentirano