Synthesis and characterization of N-phenolyl amino acid derivatives of novel spiro cyclotriphosphazenes

In this thesis, it is aimed to synthesize new spiro cyclotriphosphazene structures containing cinnamic acid derivatives with biphenyl substituted cyclotriphosphazene ring in the center and carrying amino acid structures in the side groups and to explain their structural characterizations by spectroscopic methods. For this purpose, firstly, 4-hydroxybenzaldehyde (HBA) and 4-hydroxy-3-methoxybenzaldehyde (HMBA) compounds were synthesized as 4-hydroxycinnamic acid (HCA) and 4-hydroxy-3-methoxycinnamic acid (HMCA), respectively, from the reactions of piperidine in the presence of malonic acid in pyridine. In the second step, these synthesized cinnamic acids (HCA, HMCA) were interacted with alanine and phenylalanine amino acids separately according to DCC methodology to obtain six N-phenolyl amino acid derivatives (HCA-Ala-OCH3, HCA-Phe-OCH3, HMCA-Ala-OCH3, HMCA-Phe-OCH3, HNtCA-Ala-OCH3, HNtCA-Phe-OCH3). New cyclotriphosphazene compounds (CRG-CA-Ala-OCH3, CRG-CA-Phe-OCH3, CRG-MCA-Ala-OCH3, CRG-MCA-Phe-OCH3, CRG-NtCA-Ala-OCH3, CRG-NtCA-Phe-OCH3)) were synthesized for the first time in this study by the interaction of these N-phenolyl amino acid compounds with dispirophosphazene compound (CRG) in acetone in the presence of potassium carbonate (K2CO3). Structural characterizations of the synthesized cinnamic acid and amino acid derivatives were elucidated by 1H and 13C-APT NMR spectroscopy methods. In addition to these methods, the structures of phosphazene compounds were successfully characterized using 31P and HETCOR (2D) NMR spectroscopic methods.