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α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives

Marina Pavlovna Vlasenko 1
Marina Pavlovna Vlasenko
, 
Alexander Fedorovich Pozharskii 1
Alexander Fedorovich Pozharskii
,  , 
Valery Anatol'evich Ozeryanskii 1
Valery Anatol'evich Ozeryanskii
, 
Gennadii Sergeevich Borodkin 3
Gennadii Sergeevich Borodkin
1 Department of Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
2 North-Caucasus Federal University, Stavropol, Russian Federation
3 Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
10.1016/j.mencom.2023.02.015
Published 2023-02-13
Communication , Volume 33, Issue 2, 197-200
2
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Vlasenko M. P. et al. α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 197-200.
GOST all authors (up to 50) Copy
Vlasenko M. P., Pozharskii A. F., Demidov O. P., Ozeryanskii V. A., Borodkin G. S. α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 197-200.
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TY - JOUR
DO - 10.1016/j.mencom.2023.02.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.015
TI - α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives
T2 - Mendeleev Communications
AU - Vlasenko, Marina Pavlovna
AU - Pozharskii, Alexander Fedorovich
AU - Demidov, Oleg Petrovich
AU - Ozeryanskii, Valery Anatol'evich
AU - Borodkin, Gennadii Sergeevich
PY - 2023
DA - 2023/02/13
PB - Mendeleev Communications
SP - 197-200
IS - 2
VL - 33
ER -
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@article{2023_Vlasenko,
author = {Marina Pavlovna Vlasenko and Alexander Fedorovich Pozharskii and Oleg Petrovich Demidov and Valery Anatol'evich Ozeryanskii and Gennadii Sergeevich Borodkin},
title = {α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.015},
number = {2},
pages = {197--200},
doi = {10.1016/j.mencom.2023.02.015}
}
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Vlasenko, Marina Pavlovna, et al. “α-Amino acid-assisted autoxidation of naphthalene proton sponge affording 1,4-naphthoquinone nitrogen derivatives.” Mendeleev Communications, vol. 33, no. 2, Feb. 2023, pp. 197-200. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.015.

Keywords

1
4-naphthoquinone
amino acids
autoxidation.
hydrolysis
proton sponge

Abstract

1,8-Bis(dimethylamino)naphthalene (naphthalene proton sponge) equipped at position 4 with N-terminal α-amino acid residues undergoes unprecedented easy autoxidation in basic medium forming 5-dimethylamino-1,4-naphthoquinone along with minor amounts of its derivatives. The new reaction is of interest against the background of wide distribution of 1,4-naphthoquinones in nature, their high biological significance and extremely limited information on nitrogen compounds of this series.

References

.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
.
Organocatalysts Derived from Unnatural α-Amino Acids: Scope and Applications.
Agirre M., Arrieta A., Arrastia I., Cossío F.P.
Chemistry - An Asian Journal, 2018
.
Anti-cancer activities of 1,4-naphthoquinones: a QSAR study.
Verma R.P.
Anti-Cancer Agents in Medicinal Chemistry, 2006
.
Polyakova S.K., Balashova T.V., Rumyantcev R.V., Arsenyev M.V., Fukin G.K., Chesnokov S.A.
Mendeleev Communications, 2021
.
Proton-Sponge-Like Superbases Built on the Benzo[h ]quinoline Platform
Ozeryanskii V.A., Pozharskii A.F.
European Journal of Organic Chemistry, 2018
.
peri-Naphthylenediamines
Ozeryanskii V.A., Pozharskii A.F.
Russian Chemical Bulletin, 1997
.
The first proton sponge-based amino acids: synthesis, acid–base properties and some reactivity
Ozeryanskii V.A., Gorbacheva A.Y., Pozharskii A.F., Vlasenko M.P., Tereznikov A.Y., Chernov'yants M.S.
Organic and Biomolecular Chemistry, 2015
.
Mechanism of enamine hydrolysis
Sollenberger P.Y., Martin R.B.
Journal of the American Chemical Society, 1970
.
Natural Quinone Dyes: A Review on Structure, Extraction Techniques, Analysis and Application Potential
Dulo B., Phan K., Githaiga J., Raes K., De Meester S.
Waste and Biomass Valorization, 2021
.
Zherebtsov M.A., Arsenyev M.V., Baranov E.V., Chesnokov S.A., Cherkasov V.K.
Mendeleev Communications, 2021
.
Quinone-Based Drugs: An Important Class of Molecules in Medicinal Chemistry
Ferreira V.F., de Carvalho A.S., Ferreira P.G., Lima C.G., de C. da Silva F.
Medicinal Chemistry, 2020
.
Suttie J.
2013