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2 article(s) from Ozeryanskii, Valery A

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

Ekaterina V. Kolupaeva,
Narek A. Dzhangiryan,
Alexander F. Pozharskii,
Oleg P. Demidov and
Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

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Scheme 1: Comparison of basicity (in water scale) and synthetic availability of quinoline-type azaarenes and ...

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Figure 1: Suggested amination products 6 and two resonance forms of dianion 7.

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Figure 2: Targeted dipyridoacenaphthylene 8.

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Scheme 2: Formation of complex 9 and its slow hydrolytic degradation into protic salt 5·HCl.

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Figure 3: Molecular and crystal structure of salt 5·HCl·2H₂O is strongly dominated by severe H-bonding (blue ...

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Figure 4: Selected images of the supramolecular organization of two molecules of base 5 held by 4,6-dichloror...

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Figure 5: Fragment of the crystal packing of neutral dipyridoacenaphthene 5 showing self-association via mult...

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Scheme 3: Dinitration of compound 5 and the initially assumed admixture 11.

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Scheme 4: Mononitration of compound 5.

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Figure 6: Structure of dinitroacenaphthylene 12.

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Scheme 5: Dehydrogenation of compounds 10 and 11.

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Scheme 6: Nucleophilic methoxylation of compounds 10(12).

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Figure 7: Basicity of key compounds in acetonitrile.

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Scheme 7: Electrophilic bromination of compound 5.

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Scheme 8: tele-Elimination upon interaction of dibromide 15 with pyrrolidine.

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Scheme 9: Interaction of dibromide 15 with anionic bases.

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Published 08 Feb 2024

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Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene

Semyon V. Tsybulin,
Ekaterina A. Filatova,
Alexander F. Pozharskii,
Valery A. Ozeryanskii and
Anna V. Gulevskaya

Beilstein J. Org. Chem. 2023, 19, 674–686, doi:10.3762/bjoc.19.49

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Figure 1: Proton sponge-based 1,4-diaryl-1,3-butadiynes synthesized previously and in this study.

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Figure 2: Target oligomers as push–pull and cross-conjugated π-systems.

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Scheme 1: Synthetic strategy for target oligomers 5.

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Scheme 2: Synthesis of 7-(arylethynyl)-2-ethynyl-DMAN 6.

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Scheme 3: Synthesis of 1,4-diaryl-1,3-butadiynes 5 and their salts 11.

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Figure 3: Molecular structures of compounds 5b (top), 5d (middle), and 5e (bottom).

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Figure 4: Views on the molecular backbone of compounds 5b (top), 5d (middle), and 5e (bottom) along the napht...

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Scheme 4: Transformation of butadiyne 5c into benzo[g]indole 12.

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Figure 5: Molecular structure of compound 11c: frontal (top; BF₄⁻ omitted) and side views (bottom; hydrogen a...

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Figure 6: Calculation of the qr parameter.

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Figure 7: Two π-conjugation ways in oligomers 5.

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Figure 8: UV–vis spectra of oligomers 5 (blue line), monomers 6 (red line), and butadiyne 1 (green line).

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Figure 9: UV–vis spectra of salts 11 (left), 1·2HBF₄ and 6b·HBF₄ (right) in acetonitrile.

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Figure 10: π-Conjugation pathway in salts 11b and 6b·HBF₄.

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Figure 11: Cyclic voltammograms of oligomers 5.

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Scheme 5: Possible ways of one- and two-electron oxidation of oligomers 5.

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Published 15 May 2023

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