Gold-Catalyzed Oxime-Oxime Rearrangement

Date

2015-06-05

Author

Guven, Sinem
Ozer, Merve Sinem
Kaya, Serap
Menges, Nurettin
BALCI, METİN

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

186
views

0
downloads

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.

Subject Keywords

Meyer-Schuster rearrangement, H bond functionalization, One-pot conversion, C triple bonds, Highly efficient, Atom economy, Skeletal rearrangement, Organic-synthesis, Mild conditions, Aldoximes

URI

https://hdl.handle.net/11511/47614

Journal

ORGANIC LETTERS

DOI

https://doi.org/10.1021/acs.orglett.5b01041

Collections

Test and Measurement Center In advanced Technologies (MERKEZ LABORATUVARI), Article

Suggestions

OpenMETU
Core

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...
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...
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...
Triazine herbicide imprinted monolithic column for capillary electrochromatography Asir, Suleyman; Derazshamshir, Ali; YILMAZ, FATMA; DENİZLİ, ADİL (2015-12-01) Trietazine was selectively separated from aqueous solution containing the competitor molecule cyanazine, which is similar in size and shape to the template molecule. Structural features of the molecularly imprinted column were figured out by SEM. The influence of the mobile-phase composition, applied electrical field, and pH of the mobile phase on the recognition of trietazine by the imprinted monolithic polymer has been evaluated, and the imprint effect in the trietazine-imprinted monolithic polymer was de...
Synthesis of selenophene substituted benzodithiophene and fluorinated benzothiadiazole based conjugated polymers for organic solar cell applications Cevher, Duygu; Taşkaya Aslan, Sultan; Bolayır, Eda; Hizalan Ozsoy, Gonul; UDUM, YASEMİN; Yıldırım, Erol; Toppare, Levent Kamil; Çırpan, Ali (2021-12-01) A series of alternating conjugated copolymers which contain selenophene modified benzodithiophene and fluorine bearing benzothiadiazole have been synthesized via Stille polycondensation reaction to investigate the effect of the number of fluorine atoms substituted to the benzothiadiazole. Three different polymers, PBDTSe-BT, PBDTSe-FBT and PBDTSe-FFBT, were reported and their electrochemical, spectroelectrochemical, and photovoltaic behaviors were examined. Density functional theory calculations were perfor...

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: https://hdl.handle.net/11511/47614.