Gold-Catalyzed Oxime-Oxime Rearrangement

Guven, Sinem
Ozer, Merve Sinem
Kaya, Serap
Menges, Nurettin
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.


Mechanistic Insights into the Reaction of N-Propargylated Pyrrole- and Indole-Carbaldehyde with Ammonia, Alkyl Amines, and Branched Amines: A Synthetic and Theoretical Investigation
Sari, Ozlem; Seybek, Ali Fatih; Kaya, Serap; Menges, Nurettin; ERDEM, SAFİYE; BALCI, METİN (Wiley, 2019-09-01)
The reaction of pyrrole- and indole-carbaldehydes having a propargyl group attached to the nitrogen atom with various amines was studied. The reaction with ammonia formed pyrrolo[1,2-a]pyrazine and pyrazino[1,2-a]indole while the reaction with alkylamines such as methyl, ethyl, hexyl, and benzylamines formed the corresponding pyrazinone derivatives. Unexpectedly, the reaction with allylamine and propargylamine formed pyrazine derivatives in which the allyl and propargyl groups were removed from the molecule...
Silicon tetrachloride mediated asymmetric aldol addition reaction
Tan, Duygu; Doğan, Özdemir; Department of Chemistry (2013)
Aldol addition reaction is one of the most important and most studied carbon-carbon bond forming reactions in organic chemistry. Recent studies focused on the catalytic version of this chemistry. Different from the classical Mukaiyama-type aldol reactions, chiral lewis bases have been used as promoters. In the presence of SiCl4, these reactions proceed through a cyclic transition state leading to anti aldol product as a major product with moderate-to-good diastereo and enantioselectivities. Phosphoramide de...
Free radical scavenging and antioxidative properties of 'silibin' complexes on microsomal lipid peroxidation
Basaga, H; Poli, G; Öztekin, Ceren; Aras, I (1997-03-01)
The antioxidant properties of silibin complexes, the water-soluble form silibin dihemisuccinate (SDH), and the lipid-soluble form, silibin phosphatidylcholine complex known as IdB 1016, were evaluated by studying their abilities to react with the superoxide radical anion (O-2(-)), and the hydroxyl radical (OH.). In addition, their effect on pulmonary and hepatic microsomal lipid peroxidation had been investigated. Superoxide radicals were generated by the PMS-NADH system and measured by their ability to red...
Copper-catalyzed asymmetric conjugate addition of diethylzinc to substituted chalcones using a chiral phosphine ligand
Doğan, Özdemir; Polat, Savas; Tecimer, M. Ali (2011-09-15)
A series of chiral phosphine PFAM and phosphine oxide POFAM ligands were studied for the copper-catalyzed asymmetric diethylzinc addition to enones. One of these ligands, PFAM2, was an efficient catalyst with a variety of enones to give conjugate addition products in up to 96% yield and 92% ee.
Synthesis and characterization of conducting copolymers of succinic acid bis-(4-pyrrol-1-yl-phenyl) ester and their electrochromic properties
Ertas, M; Çırpan, Ali; Toppare, Levent Kamil (Elsevier BV, 2004-05-07)
A new dipyrrolyl monomer was synthesized via the reaction between 4-pyrrol-1-yl phenol and butanedioyl dichloride. Electrochemical behavior of this monomer, succinic acid bis-(4-pyrrol-1-yl-phenyl) ester (SM) was studied. Homopolymerization was achieved by chemical and constant Current electrolysis methods. Copolymerization of SM with thiophene was performed by constant potential electrolysis in acetonitrile (AN)-tetrabutylammonium tetrafluoroborate (TBAFB) and dichloromethane (DCM)-TBAFB, solvent-electroly...
Citation Formats
S. Guven, M. S. Ozer, S. Kaya, N. Menges, and M. BALCI, “Gold-Catalyzed Oxime-Oxime Rearrangement,” ORGANIC LETTERS, pp. 2660–2663, 2015, Accessed: 00, 2020. [Online]. Available: