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Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups
Ilia V Baranovsky
1
,
Lidia S. Konstantinova
1, 2
,
Vadim V Popov
2
,
Konstantin A Lyssenko
3, 4
,
Oleg A. Rakitin
1, 2
1
Publication type: Journal Article
Publication date: 2020-08-19
PubMed ID:
32824981
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
A new synthetic pathway to four substituted imidazoles from readily available 2-((4-aryl(thienyl)-5H-1,2,3-dithiazol-5-ylidene)amino)phenols has been developed. Benzo[d]oxazol-2-yl(aryl(thienyl))methanimines were proved as key intermediates in their synthesis. The formation of an imidazole ring from two methanimine derivatives likely includes the opening of one benzoxazole ring followed by ring closure by intermolecular nucleophilic attack of the N-methanimine atom to a carbon atom of another methanimine.
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Baranovsky I. V. et al. Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups // Molecules. 2020. Vol. 25. No. 17. p. 3768.
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Baranovsky I. V., Konstantinova L. S., Tolmachev M. A., Popov V. V., A Lyssenko K., Rakitin O. A. Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups // Molecules. 2020. Vol. 25. No. 17. p. 3768.
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TY - JOUR
DO - 10.3390/molecules25173768
UR - https://www.mdpi.com/1420-3049/25/17/3768
TI - Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups
T2 - Molecules
AU - Baranovsky, Ilia V
AU - Konstantinova, Lidia S.
AU - Tolmachev, Mikhail A
AU - Popov, Vadim V
AU - A Lyssenko, Konstantin
AU - Rakitin, Oleg A.
PY - 2020
DA - 2020/08/19
PB - MDPI
SP - 3768
IS - 17
VL - 25
PMID - 32824981
SN - 1420-3049
ER -
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@article{2020_Baranovsky,
author = {Ilia V Baranovsky and Lidia S. Konstantinova and Mikhail A Tolmachev and Vadim V Popov and Konstantin A Lyssenko and Oleg A. Rakitin},
title = {Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups},
journal = {Molecules},
year = {2020},
volume = {25},
publisher = {MDPI},
month = {aug},
url = {https://www.mdpi.com/1420-3049/25/17/3768},
number = {17},
pages = {3768},
doi = {10.3390/molecules25173768}
}
Cite this
MLA
Copy
Baranovsky, Ilia V., et al. “Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2H-imidazol -4-yl)amino)-phenols from 2-((5H-1,2,3-Dithiazol -5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups.” Molecules, vol. 25, no. 17, Aug. 2020, p. 3768. https://www.mdpi.com/1420-3049/25/17/3768.