Synthesis of pyrroloquinoxalino-fused benzoxazepines and ester-containing iodopyridines

Yazıcı, Nuray Esra
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.


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