Synthesis of indole-fused new heterocycles via alkyne cyclizations

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2015

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Şeybek, Ali Fatih

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It is known that many natural and synthetic structures including indole ring have important biological activities. In this thesis, synthesis of pyridine, pyrazine and pyrazinone rings condensed to indole was carried out via alkyne cyclization reactions. In the first part, oxindole was synthesized by reduction of isatin. Then, aldehyde group and chlorine atom was introduced to the C-3 and C-2 positions via Vilsmeier-Haack reaction. After that, Sonagashira coupling reaction led to functionalize C-3 position with an alkyne group. Reaction of the resulting compound with hydrazine gave γ-carboline derivative. In the second part, C-2 and C-3 positions were functionalized by ester and alkyne groups, respectively. We attempted to synthesize diazepinone derivative by using ring closure reaction with hydrazine, but the desired compound could not obtained. In the final part, C-2 position was substituted by an aldehyde group and N-1 position was substituted by a propargyl group starting from indole-2-carboxylic acid. Then, as a result of the reactions of this key compound with variety of amines, indolopyrazine and indolopyrazinone derivatives were synthesized.

Subject Keywords

Indole., Carbolines., Pyrazines., Alkynes., Ring formation (Chemistry).

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http://etd.lib.metu.edu.tr/upload/12619129/index.pdf
https://hdl.handle.net/11511/25113

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

A. F. Şeybek, “Synthesis of indole-fused new heterocycles via alkyne cyclizations,” M.S. - Master of Science, Middle East Technical University, 2015.