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

Date

2015-11-15

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Taşkaya Aslan, Sultan
Balcı, Metin

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https://hdl.handle.net/11511/83081

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Gold catalyzed synthesis of pyrrole and indole fused heterocycles via alkyne cyclization Aslan Taşkaya, Sultan; Balcı, Metin; Department of Chemistry (2015) 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...
Gold-Catalyzed Oxime-Oxime Rearrangement Guven, Sinem; Ozer, Merve Sinem; Kaya, Serap; Menges, Nurettin; BALCI, METİN (2015-06-05) The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the lit...
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Gold nanoparticle modified conducting polymer of 4-(2,5-di(thiophen-2-yl)-1H-pyrrole-1-l) benzenamine for potential use as a biosensing material Tuncagil, Sevinc; Ozdemir, Caglar; ODACI DEMİRKOL, DİLEK; TİMUR, SUNA; Toppare, Levent Kamil (2011-08-01) Gold nanoparticle (AuNP) modified conducting polymer of 4-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)benzenamine (SNS-NH2) was used as the biosensing platform for glucose analysis. Electrochemical measurements were carried out by following the consumed oxygen due to the enzymatic reaction of glucose oxidase (GOx) at -0.7 V vs Ag/AgCl. Optimisation of pH, enzyme loading, stability experiments were carried out. Effect of NP was investigated by monitoring the signal responses at different AuNP sizes and amounts. A ...
Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products Taşkaya Aslan, Sultan; BALCI, METİN (2015-05-28) Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.

Citation Formats

S. Taşkaya Aslan and M. Balcı, “Gold catalyzed synthesis of pyrrole and indole fused heterocycles via alkyne cyclization,” 2015, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/83081.