Studies on new synthetic methodologies for synthesis of phthalazinone derivatives vicyclization of 2-ethylnylbenzohydrazides

Yaman, Tolga
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 starting material, ethyl 2-iodobenzoate was first converted to ethyl 2-ethynylbenzoate and its derivatives substituted at the alkyne carbon atom. Ester functionality was converted into the corresponding hydrazide derivatives. Gold catalyzed cyclization of 2-ethynylbenzohydrazide resulted in the formation of some target compounds. Also, heating of hydrazide derivatives at the reflux temperature of propanol gave the target compounds.  


Development of new methods for the synthesis of pyrazoles, 4-iodopyrazoles, isoxazoles and 1,2,4-oxadiazoles
Kıvrak, Arif; Zora, Metin; Department of Chemistry (2011)
Synthesis of five-membered heteroaromatic compounds such as pyrazoles, isoxazoles and 1,2,4-oxadiazoles are important for pharmaceutical industry and material science due to their applications. Although there are many methods to prepare such compounds, new variants continue to appear since they exhibit a wide range of biological and medicinal activities. In this thesis, new methods were developed for the synthesis of 4-iodopyrazoles, pyrazoles, isoxazoles, 1,2,4-oxadiazoles and/or 1,2,4-oxadiazepines. In th...
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...
Design and synthesis of benzene-fused heterocycles: aminopyridazinones, chromenopyridinones and benzopyrazoloxazepines /
Keskin, Selbi; Balcı, Metin; Department of Chemistry (2015)
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. ...
Highly sensitive and selective colorimetric probe for determination of L-cysteine in aqueous media based on Ag/Pd bimetallic nanoparticles
Farhadi, Khalil; Forough, Mehrdad; Pourhossein, Atefeh; Molaei, Rahim (2014-10-01)
The interaction between Ag/Pd bimetallic nanoparticles and cysteine was introduced as a new and high potential colorimetric probe for the selective, sensitive and low-cost recognition and monitoring of cysteine in aqueous samples. In the presence of NaCl, cysteine was able to induce the aggregation of Ag/Pd bimetallic nanoparticles thereby resulting in a change in yellowish-brown color of the Ag/Pd colloid to green. The presence of 6.6 mM NaCl in the samples decreases the electrostatic repulsion and acceler...
Facile synthesis of (4-nitrophenyl)thio-substituted 1- pyrrolines
Korkmaz, Esra; Zora, Metin; Department of Chemistry (2019)
The importance of heterocyclic compounds is enormous in synthetic organic chemistry due to their presence in bioactive molecules. Five-membered 1-pyrrolines are one of the most important classes of them. They have recently drawn great attention from synthetic chemists since they have a prominent role for the synthesis of a great number of pharmaceutical molecules. Therefore, there is intense research on their synthesis. In this project, we concentrated on the synthesis of (4-nitrophenyl)thio-substituted 1- ...
Citation Formats
T. Yaman, “Studies on new synthetic methodologies for synthesis of phthalazinone derivatives vicyclization of 2-ethylnylbenzohydrazides,” M.S. - Master of Science, Middle East Technical University, 2017.