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
Abstract
1. Introduction
2. Results and Discussion
Mechanistic Rationale
3. Experimental Section
3.1. General Methods and Materials
3.2. General Procedure for the Synthesis of 2-((4-aryl-5H-1,2,3-dithiazol-5-ylidene)amino)phenols (7)
3.3. General Procedure for the Thermolysis of 2-((4-aryl(hetaryl)-5H-1,2,3-dithiazol-5-ylidene)amino)phenols 7 in Various Solvents
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
9f | 10b | |
---|---|---|
CCDC number | 1993040 | 1993041 |
Empirical formula | C28H18F2N4O2 | C12H8N2OS |
Formula weight | 480.46 | 228.26 |
T, K | 120 | 120 |
Crystal system | Monoclinic | Monoclinic |
Space group | P21/n | P21/n |
Z (Z’) | 4 (1) | 4(1) |
a, Å | 12.3650(12) | 6.1355(5) |
b, Å | 12.9901(13) | 7.5454(6) |
c, Å | 14.3314(14) | 22.0813(19) |
α, ° | 90 | 90 |
β, ° | 107.871(2) | 94.779(2) |
γ, ° | 90 | 90 |
V, Å3 | 2190.9(4) | 1018.70(15) |
Dcalc,gcm−3 | 1.457 | 1.488 |
μ, cm−1 | 1.06 | 2.93 |
F(000) | 992 | 472 |
2θmax, ° | 58 | 58 |
Reflections collected | 25153 | 11900 |
Reflections unique (Rint) | 5821 (0.0410) | 2710 (0.0357) |
Reflections with I > 2σ(I) | 4558 | 2443 |
Variables/restraints | 333 | 149 |
R1 | 0.0425 | 0.0357 |
wR2 | 0.1092 | 0.0962 |
GOF | 1.024 | 1.036 |
Largest difference in peak/hole (e/Å3) | 0.328/−0.242 | 0.415/−0.342 |
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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, 25, 3768. https://doi.org/10.3390/molecules25173768
Baranovsky IV, Konstantinova LS, Tolmachev MA, Popov VV, A. Lyssenko K, Rakitin OA. 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; 25(17):3768. https://doi.org/10.3390/molecules25173768
Chicago/Turabian StyleBaranovsky, Ilia V., Lidia S. Konstantinova, Mikhail A. Tolmachev, Vadim V. Popov, Konstantin A. Lyssenko, and Oleg A. Rakitin. 2020. "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 25, no. 17: 3768. https://doi.org/10.3390/molecules25173768
APA StyleBaranovsky, I. V., Konstantinova, L. S., Tolmachev, M. A., Popov, V. V., A. Lyssenko, K., & Rakitin, O. A. (2020). 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, 25(17), 3768. https://doi.org/10.3390/molecules25173768