Nucleophilic and electrophilic cyclization reactions of n-alkyne substituted pyrrole derivatives

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2016

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Yenice, Işıl

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Pyrrolopyrazinone, triazinone and oxazinone derivatives were synthesized via practical methodologies. In the study, N-alkyne substituted pyrrole esters were synthesized and isolated as key compounds via copper catalyzed cross-coupling reaction. Then, key compounds underwent nucleophilic cyclization reaction with hydrazine monohydrate to yield pyrrolopyrazinone and/or pyrrolotriazinone derivatives according to electronic properties of group attached to alkyne unit. Additional study was the synthesis of pyrrolooxazinone derivatives. Key compounds were treated with iodine to achieve electrophilic cyclization reactions and iodine substituted 6-endo-dig cyclization products were obtained.

Subject Keywords

Pyrroles., Alkynes., Hydrazines., Electrophiles., Nucleophilic reactions., Ring formation (Chemistry).

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http://etd.lib.metu.edu.tr/upload/12619730/index.pdf
https://hdl.handle.net/11511/25427

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

I. Yenice, “Nucleophilic and electrophilic cyclization reactions of n-alkyne substituted pyrrole derivatives,” M.S. - Master of Science, Middle East Technical University, 2016.