Browsing by Author "Pirat, Jean-Luc. Promotor"
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Item Fluorinated phosphonate analogues of phenylalanine – synthesis, structural studies and reactivity(2017) Kwiczak, Joanna Marianna; Pluskota-Karwatka, Donata. Promotor; Pirat, Jean-Luc. Promotorα-Aminophosphonates containing in their structure fluorine atom(s) are bioactive compounds. Due to their biological and pharmacological activities, they have found a wide range of applications in medicinal and agricultural chemistry. First aim of the doctoral dissertation was the synthesis and structural characterization of phosphonate analogues of phenylalanine containing in the phenyl ring different number of fluorine atoms, as potential inhibitors of aminopeptidase. α-Aminophosphonates were synthesized by one-pot two steps reaction. First, imine was generated, followed by the nucleophilic addition of diethyl phosphite. What is more, a convenient method for the synthesis of fluorinated aldehydes, which were not commercially available, was developed. In this work, novel monodeprotection method of diethyl phosphonate group by LiI leading to corresponding monosalt, and deprotection by Me3SiBr resulted in aminophosphonic acid, were developed. Additionally, reactivity of α-aminophosphonates towards aromatic nucleophilic substitution was studied. A large library of para substituted fluorinated analogues of phenylalanine was synthesized in the reactions with different nucleophiles such as thiolates, amines and phenolates.