Synthesis of pyrroloquinoxalino-fused benzoxazepines and ester-containing iodopyridines

Download

index.pdf

Date

2013

Author

Yazıcı, Nuray Esra

Metadata

Show full item record

Item Usage Stats

59
views

17
downloads

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]quinoxalino[1,2-d][1,4]benzoxazepine derivatives starting from pyrrolo-substituted anilines and o-propargyloxybenzaldehydes. First of all, the synthesis of pyrrolo-substituted anilines was accomplished. Then, o-propargylation of benzaldehyde derivatives was performed. The reaction between pyrrolo-substituted anilines and o-propargyloxybenzaldehydes have afforded pentacyclic pyrroloquinoxalino-fused benzoxazepine molecules in one pot manner. For the synthesis of benzoxazepine derivatives, InCl3 was used as a Lewis acid catalyst in order to initiate electrophilic cyclization. In the second part of the study, the synthesis of ester-containing iodopyridines was performed in the presence of molecular iodine. In the course of this study, the synthesis of 5-iodopyridine-2,3-dicarboxylate was achieved through electrophilic cyclization of dimethyl 2-(prop-2-ynylamino)maleate in the presence of I2 and NaHCO3. The synthesized iodopyridine molecule was further functionalized by the Sonogashira coupling using terminal alkynes.

Subject Keywords

Azepines, Aniline, Pyridine, Aldehydes, Heterocyclic compounds

URI

http://etd.lib.metu.edu.tr/upload/12616189/index.pdf
https://hdl.handle.net/11511/22769

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

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...
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 6-halogen-substituted 2-methylene-2,3dihydro-1,4-oxazepine derivatives İbiş, Özge; Zora, Metin; Department of Chemistry (2017) Heterocyclic compounds are important since they are present in life naturally or synthetically. Among heterocyclic compounds, seven-membered 1,4-oxazepines are giving more attention than ever due to their wide range of biological and medicinal activities. There are many studies about their synthesis and new ones continue to appear. In this study, synthesis of halogen-substituted 1,4-oxazepine derivatives was investigated, which may have potential for biological studies. For this purpose, α,β-alkynic ketone ...
Synthesis of indole fused heterocyclic compounds Kaptı, Tolga; Balcı, Metin; Department of Chemistry (2013) Nitrogen containing heterocyclic compounds show wide range of biological activities so their syntheses have always been attractive area in organic chemistry. Indole derivatives, which are one of the important example of these biological active compound, are precursors to many pharmaceuticals. The aim of this research is to develop new synthetic methodologies leading to the synthesis of new derivatives of pyrimidoindole and quinoline, which have been found to show important biological activities. In this stu...
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...

Citation Formats

N. E. Yazıcı, “Synthesis of pyrroloquinoxalino-fused benzoxazepines and ester-containing iodopyridines,” M.S. - Master of Science, Middle East Technical University, 2013.