Synthesis of pyrroloquinoxalino-fused benzoxazepines and ester-containing iodopyridines

Date

2013

Author

Yazıcı, Nuray Esra

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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

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Graduate School of Natural and Applied Sciences, Thesis