Development of new synthetic methodologies for furan fused heterocycles

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2013

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Ergun, Merve

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Furopyranones and furopyrrolones are furan-fused bicyclic heterocycles containing pyranone and pyrrolone framework respectively. Many natural products and pharmaceutical agents include these core structures. In this study, new synthetic methodologies were developed for the synthesis of furopyranone and furopyrrolone derivatives. In the first section of this thesis, methyl 2-(2-methoxy-2-oxoethyl)-3-furoate was hydrolyzed forming 2-(carboxymethyl)-3-furoic acid which underwent intramolecular cyclization reaction using two different methodologies forming furopyranone derivatives. In the second part of the study, 2-(carboxymethyl)-3-furoic acid was regioselectively converted to acyl azide, which was accomplished by utilizing the reactivity differences between the two acid functionalities within the molecule. This acyl azide was then transformed into urea derivative to perform cyclization reaction yielding a new furan-fused heterocycle, furopyrrolone. In both parts of this study, ring closure reactions were achieved benefiting from the reactivities of different carbonyl groups within the molecules

Subject Keywords

Furans., Isocyanates., Cyclopolymerization., Ring formation (Chemistry).

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http://etd.lib.metu.edu.tr/upload/12615337/index.pdf
https://hdl.handle.net/11511/22426

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

M. Ergun, “Development of new synthetic methodologies for furan fused heterocycles,” M.S. - Master of Science, Middle East Technical University, 2013.