Gold catalyzed synthesis of pyrrole and indole fused heterocycles via alkyne cyclization

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2015
Aslan Taşkaya, Sultan
New methodologies were developed for the synthesis of pyrrolo- and indolo-oxazin1-one derivatives. In the first section of this thesis, various N-propargyl pyrrole and indole esters were efficiently converted into corresponding carboxylic acids which then underwent intramolecular cyclization reaction with AuCl3 to give 6-exo-dig cyclization products. In the second part of the study, 6-exo-dig pyrrolo- and indolo- oxazinone derivatives were treated with TFA in order to achieve double bond isomerization. Some of the 6-exo-dig cyclic double bonds underwent isomerization to 6-endo-cyclic compounds upon treatment with TFA. The experimental results were supported by DFT calculations. Moreover, the cyclization reaction of 1-prop-2-ynyl1H-pyrrole-2-carboxylic acid in the presence of alcohols catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.
Citation Formats
S. Aslan Taşkaya, “Gold catalyzed synthesis of pyrrole and indole fused heterocycles via alkyne cyclization,” M.S. - Master of Science, Middle East Technical University, 2015.