SYNTHESIS OF NEW AZIRIDINE DERIVATIVES AS POTENTIAL PIPERAZINE PRECURSORS

Download

Thesis_Final.pdf

Date

2022-7-19

Author

Bayat, Duygu

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

319
views

153
downloads

Aziridines are three-membered heterocyclic compounds. They have significant properties in organic chemistry and medicinal chemistry. Many natural products have aziridines as medicines to treat various disorders. Especially, they are essential intermediates in the synthesis of heterocyclic frameworks. Moreover, aziridines can be easily transformed into diverse types of biologically active compounds. Other remarkable heterocyclic compounds are piperazines, known as six-membered rings with two nitrogen atoms at 1,4-position in the structure. Similarly, critical pharmacological compounds, especially some antibiotics, contain piperazine structures. Aziridine-fused piperazine precursors are rare compounds due to their extremely high ring strain. They have tremendous potential to be active biological compounds. In addition to that, aziridine-fused piperazine precursors can be easily converted to functionalized piperazine structures. However, the characterizable and isolable ones are limited in the literature. In this study, different aziridines were obtained by using the Gabriel-Cromwell strategy. Starting with aryl vinyl ketones, bromination was done first; then chiral aminoalcohol was reacted with dibromocompound to get chiral aziridines. In order to replace hydroxyl group with amino group, hydroxy group was tosylated and then reacted with azide. Reduction of azide leads to intramolecular cyclization over the ketone carbonyl. As a result of this cyclization, novel aziridine-fused piperazine imines were obtained in moderate to good yields (36-75%). This strategy can be used for the synthesis of highly functionalized piperazine derivatives.

Subject Keywords

Aziridine, Gabriel-Cromwell Reaction, piperazine precursors.

URI

https://hdl.handle.net/11511/98548

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

REGIOSELECTIVE RING OPENING REACTIONS OF AZIRIDINE-2-PHOSPHONATES AND AZIRIDINE BASED CHIRAL LIGANDS FOR CATALYTIC, ASYMMETRIC AZOMETHINE YLIDE CYCLOADDITIONS AND AZA-HENRY REACTION Beksultanova, Nurzhan; Doğan, Özdemir; Department of Chemistry (2021-7-16) Aziridines are small three-membered heterocyclic compounds. They are important as building blocks for many nitrogen-containing biologically active compounds and as chiral ligands in metal catalyzed asymmetric synthesis of different organic compounds. In the first part of this thesis, we have studied the ring opening reactions of various racemic and chiral aziridine-2-phosphonates. Regioselective aziridine ring opening reaction with HCl formed -amino--chlorophosphonates in 60-95 % yield and the same reacti...
Production and biochemical characterization of polyphenol oxidase from thermomyces lanuginosus Astarcı, Erhan; Bakır, Ufuk; Ögel, Zümrüt B.; Department of Biotechnology (2003) Polyphenol oxidases are enzymes that catalyze the oxidation of certain phenolic substrates to quinones in the presence of molecular oxygen. Polyphenol oxidases are widely used in several applications. In food industry, they are used for enhancement of flavor in coffee, tea and cocoa production, and determination of food quality. In medicine, they have several uses in treatments of Parkinson̕s disease, phenlyketonurea and leukemia. In wastewater treatment, they are used for the removal of phenolic pollutants...
DETERMINATION OF SIALIC ACID BY USING PLASMONIC NANOPARTICLES AKIN, EDA; Volkan, Mürvet; Ertaş, Gülay; Department of Chemistry (2022-6-22) Sialic acids are an important sub-group of nine carbon acidic sugars. Sialic acid plays a significant role in mediating and modulating a variety of physiological activities due to its widespread distribution in human body. Several pathogens and toxins also bind to sialic acid, change its level and signal pathological conditions. The identification and quantification of sialic acid levels are also significant for early detection of many diseases such as breast and colon cancer. In this study, sialic acid de...
Multicomponent ion exchange on synthetic zeolites Beşel Düzgün, Elif; Yücel, Hayrettin; Department of Chemical Engineering (2014) Zeolites are natural and synthetic microporous crystalline aluminosilicates with ion-exchange and molecular sieve properties. Zeolites consist of a three-dimensional framework of (SiO4)4- and (AlO4)5- tetrahedras, connected by a shared oxygen atom. The presence of aluminum in the aluminosilicate framework introduces a net negative charge. Zeolites are mostly used in ion exchange, adsorption processes and catalytic applications. The objective of the study was to determine and model the multicomponent ion exc...
Metal catalyzed asymmetric synthesis of thienyl-substituted pyrrolidines by 1,3-dipolar cycloaddition reaction of azomethine ylides Bulut, Merve; Doğan, Özdemir; Department of Chemistry (2019) Pyrrolidines are structurally and biologically important heterocyclic compounds. One of the efficient methods for the synthesis of these compounds is 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides with electron deficient dipolarophiles. Asymmetric synthesis of these compounds has been studied by many groups by using 1,3-DC reactions with chiral transition metal catalysts. In all these studies aryl-substituted pyrrolidines were synthesized mainly. In this thesis, heteroaryl-substituted pyrr...

Citation Formats

D. Bayat, “SYNTHESIS OF NEW AZIRIDINE DERIVATIVES AS POTENTIAL PIPERAZINE PRECURSORS,” M.S. - Master of Science, Middle East Technical University, 2022.