Synthesis of novel heterocyclic compounds with nitrogen-containing reagents
2015
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Advisor: Prof. Dr. Zehra Nüket Öcal Sunguroğlu
Abstract (EN)
N-carboxy-α-amino acid anhydrides (4-alkyl-oxazolidin-2,5-dione) are also known as Leuchs' anhydrides. Leuchs' anhydrides (NCA), peptides, polypeptides, cyclic peptides, block copolymers, are important intermediates for the preparation of drugs and drug carriers. In literature research about Leuchs' anhydride, no reactions were seen with imines. In our study, we aimed to react Leuchs' anhydrides with Schiff base to obtain imidazolidin-4-one and α-amino acid amides-Schiff base. Imidazolidin-4-one derivatives show a broad spectrum of biological activity. It is reported to be used in Anti-malaria, diabetes and Alzheimer's disease. They are used as important chiral building total synthesis of natural products, chiral auxiliary for the synthesis of amino acids and also as organacatalyst for the synthesis of various asymmetric reactions [1]. In literature research, we found that the synthesis of α-amino acid amide-Schiff base is multistep syntheses and this compound play an important role in the preparation of chiral vicinal diamines, α-amino alcohols and α-aminoketones [2]. We have made numerous experiments on reaction conditions and synthesized to α-Amino acid amide Schiff base by a short, simple and one-step method. In addition, we also prepared compounds of the amine by reduction with sodium borohydride. In important addition, we synthesized imidazolidin-4-ones by one-pot reaction. In the last step, we characterized structures of all new compounds by FTIR, 1H NMR, 13C NMR (APT) and LC-MS techniques. Keywords: Leuchs' anhydride, Schiff base, imidazolidin-4-one, a-amino acid amide- Schiff base
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Bilgesu Onur Sucu Bavkır
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Bilgesu Onur Sucu Bavkır (Doctorate thesis). Synthesis of novel heterocyclic compounds with nitrogen-containing reagents, 2015, Yıldız Technical University.
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