The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence
Pavel A Knyazev
1
,
G. Romanenko
2
,
Tatyana E Ivakhnenko
3
,
Yurii V Revinskii
4
,
V. I. Minkin
4, 5
3
Rostov Branch of the Russian Customs Academy, 20 Budennovskiy Ave., 344000 Rostov-on-Don, Russian Federation
|
Publication type: Journal Article
Publication date: 2019-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
New carboxyl-containing o-aminophenols and phenoxazines were synthesized by condensation of 3,5-di-(tert.-butyl)-quinone with p-aminobenzoic and anthranilic acids. Oxidative transformations of the o-aminophenols and intermediate o-iminoquinones occur with the formation of the ESR detected phenoxazinyl radicals, which furthermore transform to phenoxazines or the dimeric products emerged through the radical attack at the C1 carbon of a formed phenoxazine. Molecular structure of the dimer obtained by oxidation of methyl ester of 4-[3,5-di-(tert.-butyl)-1-(2′-hydroxyphenyl)amino]benzoic acid was X-ray determined. Reaction of 4-[3,5-di-(tert.-butyl)-1-(2′-hydroxyphenyl)amino]benzoic acid with thionyl chloride gives rise to the formation of a derivative of 2-oxido-3H-benzo[d,j][1,2,3]oxathiazol system, the structure of which was established using X-ray crystallography. Solutions of methyl-6,8-di-(tert.-butyl)-10H-phenoxazine-3-carboxylate solvents display intense fluorescence covering a broad spectral region in the range of 400–600 nm.
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9
Total citations:
9
Citations from 2024:
4
(44.44%)
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Ivakhnenko E. et al. The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence // Tetrahedron. 2019. Vol. 75. No. 4. pp. 538-544.
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Ivakhnenko E., Knyazev P. A., Romanenko G., Kovalenko A., Ivakhnenko T. E., Revinskii Y. V., Minkin V. I. The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence // Tetrahedron. 2019. Vol. 75. No. 4. pp. 538-544.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tet.2018.12.047
UR - https://doi.org/10.1016/j.tet.2018.12.047
TI - The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence
T2 - Tetrahedron
AU - Ivakhnenko, Eugeny
AU - Knyazev, Pavel A
AU - Romanenko, G.
AU - Kovalenko, Anastasiia
AU - Ivakhnenko, Tatyana E
AU - Revinskii, Yurii V
AU - Minkin, V. I.
PY - 2019
DA - 2019/01/01
PB - Elsevier
SP - 538-544
IS - 4
VL - 75
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{2019_Ivakhnenko,
author = {Eugeny Ivakhnenko and Pavel A Knyazev and G. Romanenko and Anastasiia Kovalenko and Tatyana E Ivakhnenko and Yurii V Revinskii and V. I. Minkin},
title = {The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence},
journal = {Tetrahedron},
year = {2019},
volume = {75},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.tet.2018.12.047},
number = {4},
pages = {538--544},
doi = {10.1016/j.tet.2018.12.047}
}
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MLA
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Ivakhnenko, Eugeny, et al. “The carboxyl derivatives of 6,8-di-(tert.-butyl)phenoxazine: Synthesis, oxidation reactions and fluorescence.” Tetrahedron, vol. 75, no. 4, Jan. 2019, pp. 538-544. https://doi.org/10.1016/j.tet.2018.12.047.
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