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

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 Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2020, Volume: 25, Number: 17, Article number : 3768, Pages count : DOI: 10.3390/molecules25173768

Authors

Baranovsky Ilia V ¹ , Konstantinova Lidia S ^1,2 , Tolmachev Mikhail A ¹ , Popov Vadim V ² , Lyssenko Konstantin A ^3,4 , Rakitin Oleg A ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia.
2	Nanotechnology Education and Research Center, South Ural State University, 454080 Chelyabinsk, Russia
3	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskiye Gory, 1, 119991 Moscow, Russia
4	G. V. Plekhanov Russian University of Economics, 36 Stremyanny Per., 117997 Moscow, Russia

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.

Baranovsky I.V. , Konstantinova L.S. , Tolmachev M.A. , Popov V.V. , Lyssenko K.A. , 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. V.25. N17. 3768 . DOI: 10.3390/molecules25173768 WOS Scopus OpenAlex

Web of science:	WOS:000569944000001
Scopus:	2-s2.0-85089817558
OpenAlex:	W3067027182

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