Synthesis of furopyrrolone and furopyridazinone derivatives: a new class of compounds

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2011

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Karahan, Emrah

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Furopyrrolone has a bicyclic structure consisting of furan and a pyrrolone ring. It is isoelectronic with isoindolinone which is also a heterocyclic organic compound. It has a bicyclic structure, consisting of a benzene ring fused to a five-membered nitrogen containing pyrrolone ring. Pyrrolones, pyrrolidines, pyrrolidinones, pyridazines and pyridazinones are precursors to many pharmaceuticals. In this project we developed new synthetic procedures leading to the synthesis of furopyrrolone derivatives. To do this, the starting compound, methyl 2-(2-methoxy-2-oxoethyl)-3-furoate, was converted to isocyanate, regioselectively. This isocyanate was converted into the corresponding urethane and/or urea derivatives by treatment with alcohol and amine, respectively. It is known that acyl chlorides are more reactive than esters and carboxylic acids. Therefore, ester was converted to more reactive compound acyl azide that was used for intramolecular cyclization to get desired furopyrrolone skeletons. In the second part, methyl 2-formylfuran-3-carboxylate was treated with hydrazine and hydrazine salts. Then, intramolecular molecular cyclization caused the formation of desired heterocycles via acyl chloride intermediate.

Subject Keywords

Chemistry., Chemical reactions.

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http://etd.lib.metu.edu.tr/upload/12612937/index.pdf
https://hdl.handle.net/11511/20360

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

E. Karahan, “Synthesis of furopyrrolone and furopyridazinone derivatives: a new class of compounds,” M.S. - Master of Science, Middle East Technical University, 2011.