Browsing by Author "Ozer, Merve Sinem"

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Gold-Catalyzed Oxime-Oxime Rearrangement
(Amer Chemical Soc, 2015) Guven, Sinem; Ozer, Merve Sinem; Kaya, Serdal; Menges, Nurettin; Balci, Metin
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 literature and is named an oximeoxime rearrangement.
Intermolecular Heterocyclization of Alkynones With 2-Mercaptoacetaldehyde Under Metal-Free Conditions: Synthesis of 2,3-Disubstituted Thiophenes
(Pergamon-elsevier Science Ltd, 2015) Vatansever, Erol Can; Kilic, Kubra; Ozer, Merve Sinem; Koza, Gani; Menges, Nurettin; Balci, Metin
A concise and regioselective approach for the synthesis of 2,3-disubstituted thiophene derivatives has been developed. The synthetic strategy relies on the reaction of an in situ generated 2-mercaptoacetaldehyde with various alkynones. Furthermore, we calculated the energy gap between the HOMO and the LUMO orbitals of all compounds and observed that the introduction of a strong electron-withdrawing group decreased the HOMO-LUMO energy gap. (C) 2015 Elsevier Ltd. All rights reserved.
Synthesis of Pyrrole-Fused C,n-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values
(Amer Chemical Soc, 2016) Ozer, Merve Sinem; Menges, Nurettin; Keskin, Selbi; Sahin, Ertan; Balci, Metin
The AgOTf-catalyzed reaction of C-2 substituted pyrrole hydrazones having an N-propargyl group was studied. The selective 6-endo-dig mode of cyclization was observed, giving rise to the formation of pyrrole-fused C,N-cyclic azomethine imine derivatives. The reaction of one azomethine imine derivative with various dipolarophiles resulted in the formation of cycloadducts having a pyrazolopyrrolopyrazine skeleton. The aromaticity of C,N-cyclic azomethine imines as well as that of pyrazolopyrrolopyrazines was determined by calculating of nucleus-independent chemical shifts values.