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

Download
index.pdf
2015
Keskin, Selbi
Show full item record
273
views
309
downloads
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.
Pyridazinones., Benzene., Pyridine., Pyrazoles.
http://etd.lib.metu.edu.tr/upload/12619089/index.pdf
https://hdl.handle.net/11511/25195
Graduate School of Natural and Applied Sciences, Thesis

Suggestions

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 ...
Novel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties
Doğan, Kübra; Forough, M; Persil Çetinkol, Özgül (2020-09-01)
Benzothiazoles are known to possess a number of biological activities and therefore are considered to be an important scaffold in the design and synthesis of pharmacophores. In this study, an improved synthesis method for novel fluorescent benzothiazole-based cyclic azacyanine (CAC) dyes bearing different electron-donating/withdrawing groups on their scaffold is presented. The improved method enabled us to increase the synthesis yield for the previously reported CACs. More importantly, it allowed us to synt...
Design, synthesis and biological evaluation of novel 1,3-diarylpyrazoles as cyclooxygenase inhibitors, antiplatelet and anticancer agents.
Inceler, Nazan; ÖZKAN, YEŞİM; Turan, Nilufer Nermin; Kahraman, Deniz Cansen; Atalay, Rengül; BAYTAŞ, Sultan (2018-04-06)
With the aim of achieving new compounds possessing both anti-inflammatory and antiplatelet activities, we synthesized (E)-3-[3-(pyridin-3/4-yl)-1-(phenyl/sulfonylmethylphenyl)-1H-pyrazol-4-yl]acrylamides, and evaluated their COX-1 and COX-2 inhibitory and antiplatelet activities. Since COX-2 inhibitory and antiplatelet compounds have anticancer potential, we also screened their antiproliferative effects against three human cancer cell lines. Compounds 5n, 5p, 5s, 10d, 10g and 10i were determined as dual COX...
Citation Formats
S. Keskin, “Design and synthesis of benzene-fused heterocycles: aminopyridazinones, chromenopyridinones and benzopyrazoloxazepines /,” Ph.D. - Doctoral Program, Middle East Technical University, 2015.
METU IIS - Integrated Information Service open@metu.edu.tr