Design and synthesis of benzene-fused heterocycles: aminopyridazinones, chromenopyridinones and benzopyrazoloxazepines /

Keskin, Selbi
The interest in the synthesis of heterocyclic compounds has increased day by day due to their biological activities. This study focuses on the synthesis of different benzene-fused heterocycles. In the first part, we synthesized novel class of compounds, 4-aminophthalazin-1(2H)-ones starting from methyl 2-(2-methoxy-2-oxoethyl)-benzoate. Methylene group in this starting material was oxidized to the corresponding ketoester. Reaction of ketoesters with hydrazine derivatives provided the hydrazone derivatives. An intramolecular cyclization in the presence of thionyl chloride formed fused pyridazinone skeleton. Hydrolysis of the remaining ester groups and transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the isocyanates. Reaction of the isocyanates with methanol and water produced urethane and aminopyridazinone derivatives, respectively. In the second part of this thesis, a concise and regioselective approach to the synthesis of chromenopyridine and chromenopyridinone derivatives was developed. The synthetic strategy relies on the O-propargylation of aromatic hydroxyaldehydes followed by the reaction with propargylamine. The intramolecular cycloaddition reaction between the alkyne and azadiene, which was formed as an intermediate, furnished the desired skeleton. Benzopyrazoloxazepine and benzopyrazoloxazocine skeletons were also formed via alkyne cyclization in the presence of gold catalyst.


Synthesis of Iodo-substituted spiro-fused pyridine derivatives
Teke, Ecem; Zora, Metin; Department of Chemistry (2014)
Spiro cyclic molecules have gained significance because of their biological activities and electronic properties. Spiro frameworks are present in importance natural products and optoelectronic materials. Moreover, due to steric strain, the presence of a spiro carbon atom induces easy rearrangements that can lead to different cyclic products. Although there are some methods to synthesize spiro compounds, the synthesis of iodo-substituted spiro-fused pyridines have not been studied. Accordingly, in this thesis...
Synthesis of pyrroloquinoxalino-fused benzoxazepines and ester-containing iodopyridines
Yazıcı, Nuray Esra; Zora, Metin; Department of Chemistry (2013)
Heterocyclic fused compounds have gained considerable attention for pharmaceutical applications since they show remarkable biological activities such as antitumor and/or anticancer activities. In particular, the synthesis of seven-membered ring embedded molecules is a challenging issue among organic chemists. Therefore, we have aimed to develop one-pot reaction for the synthesis of seven-membered-fused heterocyclic compounds. We have developed a new methodology for the synthesis of pyrrolo[2',1':3,4]quinoxa...
Studies on new synthetic methodologies for synthesis of phthalazinone derivatives vicyclization of 2-ethylnylbenzohydrazides
Yaman, Tolga; Doğan, Özdemir; Balcı, Metin; Department of Chemistry (2017)
Nitrogen-containing heterocyclic compounds display a wide range of biological activities, which account for the increasing interest for their synthesis. In particular, the pyridazinone and phthalazinone derivatives represent a privileged structural motif in biologically active natural products and pharmaceutical compounds. For example, 4-aminophthalizinones have shown potential as anticancer agents. We have developed a methodology for the synthesis of various substituted phthalazinone derivatives. The start...
Synthesis of metal binding artificial amino acids
Eşan, Gözde; Özçubukçu, Salih; Department of Chemistry (2014)
A large variety of peptides with different physical and chemical properties can be acquired by using different amino acids. Through chemical peptide synthesis, utilizing unnatural synthetic amino acids beside 21 natural amino acids, divergent peptides can also be obtained easily. Specifically amino acid and peptide conjugates of metals have received considerable attention due to their important role in many biological processes with unique structural properties. Moreover, it is well known that some metal io...
Investigation of neutron sensitivity of un-doped and Dy-doped CaB4O7 for thermoluminescence applications
Iflazoglu, Sera; Yılmaz, Ayşen; KAFADAR, VURAL EMİR; YAZICI, AHMET NECMEDDİN (2018-09-01)
In this study, thermoluminescence characteristics of un-doped and Dy-doped calcium tetraborate (CaB4O7) compounds are reported. The polycrystalline powder samples of un-doped and Dy-doped CaB4O7 were prepared by a solid-state reaction at high-temperature method. The identification and characteristics of the obtained compounds were determined by X-ray diffraction, Fourier transform infrared analysis, differential thermal analysis, thermogravimetric analysis, and scanning electron microscopy. The glow curves ...
Citation Formats
S. Keskin, “Design and synthesis of benzene-fused heterocycles: aminopyridazinones, chromenopyridinones and benzopyrazoloxazepines /,” Ph.D. - Doctoral Program, Middle East Technical University, 2015.