Development of new synthetic methodologies for isoquinolone and isoindolinone derivatives

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2010

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Müjde, Berk

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Due to the wide range of physiological activities, heterocycles containing nitrogen and oxygen have always attracted the interest of chemists. The objective of this research is to develop new synthetic routes to the synthesis of isoquinolone and isoindolinone derivatives starting from 2-(2-carboxyethyl)benzoic acid and homophthalic acid, respectively. The half ester produced from 2-(2-carboxyethyl)benzoic acid was an important key compound for the synthesis of new isoquinolone derivatives which are expected to be biologically active. The corresponding acyl azides and isocyanates were generatedwhich might be used as a precursors to construct a variety of isoquinolone derivatives. Transformation of acyl azides into urea derivatives followed by ring-closure under the basic conditions provided isoquinolones. Bromo- and methoxyhomophthalic acid derivatives were synthesized to increase in variety of isoindolinone derivative. Then corresponding anhydrides were generated to further reactions for synthesis of isoindolinone derivatives. Surprisingly, tetrazolinone derivatives are also formed by 1,3 dipolar cycloaddition. Whole products were conscientiously purified and characterized. In addition, the similar methodology which was used for the synthesis of isoquinolone derivatives, was applied to 2-(carboxymethyl)furan-3-carboxylic acid to synthesize new nitrogen and oxygen containing heterocycles.

Subject Keywords

Chemistry., QD Organic Chemistry 241-441 .

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http://etd.lib.metu.edu.tr/upload/3/12612145/index.pdf
https://hdl.handle.net/11511/19549

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

B. Müjde, “Development of new synthetic methodologies for isoquinolone and isoindolinone derivatives,” M.S. - Master of Science, Middle East Technical University, 2010.