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4 article(s) from Balci, Metin

Bromination of endo-7-norbornene derivatives revisited: failure of a computational NMR method in elucidating the configuration of an organic structure

Demet Demirci Gültekin,
Arif Daştan,
Yavuz Taşkesenligil,
Cavit Kazaz,
Yunus Zorlu and
Metin Balci

Beilstein J. Org. Chem. 2023, 19, 764–770, doi:10.3762/bjoc.19.56

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Scheme 1: Bromination of endo-7-bromonorbornene.

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Figure 1: Structure 6 (our assignment) and structure 7 revised by Novitskiy and Kutateladze.

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Figure 2: W or M orientaition in norbornane and the corresponding coupling constants.

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Figure 3: The determined structure 6 by NMR experiments and the proposed structure 7 by computional NMR.

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Figure 4: The normal and expanded ¹H NMR spectra of compound 6.

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Figure 5: γ-Gauche effects caused by bromine atoms in 3, 5, and 6.

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Figure 6: NOE-Diff experiment. Double resonance experiment. Irradiation at the resonance frequency of protons...

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Figure 7: NOE-Diff experiment. Irradiation at the resonance frequency of proton H₇ (4.23 ppm).

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Scheme 2: Our mechanism suggested for the formation of 6 [4].

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Scheme 3: The mechanism suggested by Novitskiy and Kutateladze for the formation of 7 [3].

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Figure 8: A) Molecular structure of the compound 6 with displacement ellipsoids drawn at the 30% probability ...

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Published 02 Jun 2023

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Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

Işıl Yenice,
Sinan Basceken and
Metin Balci

Beilstein J. Org. Chem. 2017, 13, 825–834, doi:10.3762/bjoc.13.83

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Figure 1: Structures of some natural products containing pyrazinone and aminotriazonone skeletons.

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Figure 2: Structures of some natural products containing a pyrrolopyrazinone moiety.

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Figure 3: N-alkyne substituted pyrrole esters 7a–d.

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Scheme 1: Synthesis of N-alkyne substituted methyl 1H-pyrrole-2-carboxylate derivatives 7a–d.

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Scheme 2: Nucleophilic cyclization reaction of compounds 7a–d and acetylation of 12c.

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Figure 4: Correlations of olefinic proton in 12c and methylene protons in 13c and 16 with the relevant carbon...

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Figure 5: Single-crystal X-ray structure of 12c shown with 40% probability displacement ellipsoids.

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Scheme 3: Synthesis of 16.

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Figure 6: The structure of allene 17 formed during the reaction of 7d with a base.

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Scheme 4: Proposed reaction mechanism of nucleophilic cyclization reaction of 7.

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Scheme 5: Electrophilic cyclization reactions of 19a–c with iodine.

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Figure 7: Single-crystal X-ray structure of 19c shown with 40% probability displacement ellipsoids.

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Scheme 6: Proposed reaction mechanism of electrophilic cyclization reaction of 7c.

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Figure 8: Potential energy proﬁle related to the formation of pyrrolooxazinone 19c in the polarizable continu...

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Published 04 May 2017

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Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products

Sultan Taskaya,
Nurettin Menges and
Metin Balci

Beilstein J. Org. Chem. 2015, 11, 897–905, doi:10.3762/bjoc.11.101

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Figure 1: Structures of some marine natural products 1–4.

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Figure 2: Structures 5–7.

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Scheme 1: Intramolecular gold(I)-catalyzed cyclization reaction of 8 to give 9 and 10.

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Scheme 2: Synthesis of 13 and its reaction with AuCl₃.

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Scheme 3: Synthesis of 6.

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Figure 3: Geometry optimized structures of 6, 7, 30 and 31.

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Scheme 4: Reaction of 15 with Au(I)/AgOTf in the presence of EtOH and CD₃OD.

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Scheme 5: Reaction of 7 with Au(I)/AgOTf in the presence of EtOH.

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Scheme 6: Proposed reaction mechanism for the intramolecular gold-catalyzed cyclization followed by EtOH addi...

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Published 28 May 2015

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Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study

Benan Kilbas and
Metin Balci

Beilstein J. Org. Chem. 2011, 7, 246–253, doi:10.3762/bjoc.7.33

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Scheme 1: General route to oxazolidinones via a palladium-catalyzed reaction.

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Figure 1: Metal–olefin complexation from the anti-face of the double bond.

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Figure 2: Cyclic systems with enantiotopic leaving groups at allylic positions.

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Scheme 2: The cycloheptatriene–norcaradiene equilibrium.

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Scheme 3: Synthesis of oxazolidinone 9 starting from carboxymethyl cycloheptatriene 5a.

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Scheme 4: Attempted isomerization of 7 to 10.

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Scheme 5: Synthesis of oxazolidinones 17 and 20.

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Scheme 6: The mechanism for the formation of oxazolidinones [3].

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Figure 3: Nucleophilic attack on the double bond from the leaving group's side.

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Published 24 Feb 2011

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