Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2 H-imidazol-4-yl)amino)-phenols from 2-((5 H-1,2,3-Dithiazol-5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups

Ilia V Baranovsky; Lidia S Konstantinova; Mikhail A Tolmachev; Vadim V Popov; Konstantin A Lyssenko; Oleg A Rakitin

doi:10.3390/molecules25173768

Synthesis of 2-((2-(Benzo[d]oxazol-2-yl)-2 H-imidazol-4-yl)amino)-phenols from 2-((5 H-1,2,3-Dithiazol-5-ylidene)amino)phenols through Unprecedented Formation of Imidazole Ring from Two Methanimino Groups

Molecules. 2020 Aug 19;25(17):3768. doi: 10.3390/molecules25173768.

Authors

Ilia V Baranovsky¹, Lidia S Konstantinova^{1

2}, Mikhail A Tolmachev¹, Vadim V Popov², Konstantin A Lyssenko^{3

4}, Oleg A Rakitin^{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.

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.

Keywords: 5-Arylimino-1,2,3-dithiazoles; X-ray analysis; four substituted 2H-imidazol-4-amines; sulfur-nitrogen heterocycles; thermolysis.

MeSH terms

Benzoxazoles / chemistry*
Crystallography, X-Ray
Imidazoles / chemistry*
Imines / chemistry*
Models, Molecular
Molecular Structure
Phenols / chemical synthesis*

Substances

Benzoxazoles
Imidazoles
Imines
Phenols
imidazole