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Communication

2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide

by
Ida A. Lupanova
,
Dzhamilya N. Konshina
,
Nikita A. Elkov
and
Valery V. Konshin
*
Department of Chemistry and High Technology, Kuban State University, Stavropolskayast 149, 350040 Krasnodar, Russia
*
Author to whom correspondence should be addressed.
Molbank 2022, 2022(1), M1312; https://doi.org/10.3390/M1312
Submission received: 9 December 2021 / Revised: 22 December 2021 / Accepted: 24 December 2021 / Published: 31 December 2021
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Abstract

:
Reaction of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazane with boron trifluoride diethyl etherate (5 equiv) in the presence of triethylamine (3 equiv) in toluene medium gave “boratetrazine”—2-(4-(dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro -1,2,4,5,3-tetrazaborinin-2-ium-3-ide in a 58% yield.

1. Introduction

Various boron chelates are some of the most common fluorophores, finding widespread practical application in bioimaging [1], as molecular reporters and chemodosimeters [2,3], in sensors [4,5,6], in optoelectronic applications [7,8,9] and others. The most studied are BODIPY 1 [10,11,12] and their structural analogs 2 [13], BOPHY 3 [14], boron difluoride 1,3-diketonates 4 [15] and 1,3-ketoiminates 5 [16]. Difluoroboron derivatives of different types of hydrazones 6 [17], such as N-acylhydrazones 7 [18] and azohydrazones (formazanes) 8 [19] (Figure 1), are also of interest and are being extensively studied at the present time.
The pioneering work on the reaction of formazans with boron trifluoride diethyl etherate showed it to afford triphenyltetrazolium tetrafluoroborate [20]. Later, the first representatives of boron formazanate complexes, “boratetrazines” 10, were obtained by the reaction of formazans with diboron tetraacetate (in situ synthesized from boric acid, acetic acid and acetic anhydride) (Scheme 1) [21].
The purposeful study of boron formazanates was started in 2007 by Gilroy et al. [22]. Later, efficient synthesis of them was proposed in toluene medium in the presence of triethylamine [23]. Different derivatives based on cyano- [24], nitro- [25] and triarylformazans [19,26,27,28,29] have been obtained.
The reaction between boron trilfuoride etherate and more complex substrates containing additional groups, which can coordinate to the boron, proceeds nontrivially, as in the case of 11–14 (Figure 2), where coordination is realized through the oxygen atom [30,31,32,33].
To date, only one representative of “boratetrazines” having a donor N,N-dialkylamino group has been described [34]. It was prepared from cyanoformazan containing the 4-(dimethylamino)phenyl fragment in the N1 and N5 positions. The aim of the present work was to study the reaction of triarylformazan containing the N,N-dialkylamino group in the N1 position with boron trifluoride etherate.

2. Results and Discussion

To begin, 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazan 17 was synthesized from phenylhydrazone benzaldehyde 15 [35] and diazotized N,N-dimethyl-p-phenylenediamine in a pyridine medium (Scheme 2). The target formazane 17 was purified by flash chromatography and recrystallization from ethanol. Its physical constants and spectral data are in agreement with the literature data [36].
The reaction of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazan 17 with fivefold excess boron trifluoride diethyl etherate was performed in the presence of threefold excess triethylamine in toluene medium. Monitoring of the reaction by analytical thin-layer chromatography (TLC) showed that complete conversion was achieved after 5 h of stirring the reaction mixture at 90 °C (Scheme 3).
After flash chromatography and recrystallization from ethanol, the yield of target “boratetrazine” 18 was 58%.
The structure of 2-(4-(dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide 18 was unambiguously confirmed by single-crystal X-ray analysis (Figure 3) and 1H, 13C, 11B, 19F NMR and mass spectrometry.
In conclusion, it was shown that the reaction of triarylformazane with a donor dimethylamino group 17 with boron trifluoride etherate leads to the formation of “boratetetrazine” 18. The notion that the coordination of boron occurs only due to the azohydrazone fragment was confirmed.

3. Materials and Methods

The reactions were monitored by thin-layer chromatography (Sorbfil, Imid Ltd., Krasnodar, Russia). The 1H-NMR, 13C-NMR, 11B-NMR and 19F-NMR spectra were acquired on ECA400 (JEOL) (400 and 100 MHz, respectively) spectrometers in CDCl3 at room temperature. The chemical shifts δ were measured in ppm with reference to the residual solvent resonances (1H: CDCl3, δ = 7.25 ppm; 13C: CDCl3, δ = 77.2 ppm). The splitting patterns are referred to as s, singlet; d, doublet; t, triplet; m, multiplet. Coupling constants (J) are given in hertz. IR spectra were recorded on an IR Prestige (Shimadzu, Kyoto, Japan), using tablets of samples with KBr. High-resolution and accurate mass measurements were carried out using a Bruker MaXis Impact (electrospray ionization/time of flight). The melting points were determined on a Stuart SMP30 apparatus and left uncorrected. The commercial reagents employed in the synthesis were benzaldehyde (for synthesis, ≥99.0%, Aldrich, St. Louis, MO, USA), Phenylhydrazine (for synthesis, ≥97%, Aldrich, St. Louis, MO, USA) and N,N-Dimethyl-p-phenylenediamine dihydrochloride (≥99%, Vekton, Russia), boron trifluoride diethyl etherate (for synthesis, ≥97%, Aldrich, St. Louis, MO, USA). CCDC 1919508 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at http://www.ccdc.cam.ac.uk/or (accessed on 29 November 2021) from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44-1223-336033; E-mail: [email protected].

3.1. 1-(4-(Dimethylamino)phenyl)-3,5-diphenylformazan (17)

Diazonium salt solution (obtained from 3.52 g (0.0168 mol) N,N-dimethyl-p-phenylenediamine dihydrochloride, 1.16 g NaNO2 and 4 mL conc. HCl in 30 mL water) was added to a solution of 3 g (0.0153 mol) of phenylhydrazone benzaldehyde in 100 mL pyridine at −5 °C. Then, a solution of 2.5 g NaOH in 6 mL water was added and stirred at −5 °C for 1 h. Then, the temperature was raised to 15 °C and the reaction mixture was allowed to stand for 6 h. The reaction mixture was poured into 500 mL of cooled 2M HCl; the resulting brown precipitate was filtered off, washed on a filter with water and dried in the desiccator. It was purified by flash chromatography on alumina (neutral) eluting with a hexane–dichloromethane mixture (10:1) and subsequent recrystallization from ethanol. Yield 2.78 g (53%); violet–black microcrystalline solid; mp 184–185 °C. IR (KBr): ν = 3086, 3051 (Csp2-H), 2918, 2852, 2806 (Csp3-H), 1595, 1510, 1494, 1438, 1377, 1307, 1234, 1147, 985, 817 cm−1 (SI, Figure S1). 1H NMR (CDCl3, 399.78 MHz): δ = 3.09 (s, 6H, CH3), 6.74–6.78 (m, 2H, CH), 6.98–7.04 (m, 1H, CH), 7.32–7.45 (m, 7H, CH), 7.82–7.87 (m, 2H, CH), 8.14–8.17 (m, 2H, CH), 14.92 (s, 1H, NH) (SI, Figure S2). 13C NMR (CDCl3, 100.5 MHz): δ = 40.3 (CH3), 111.8 (CH), 114.7 (CH), 122.5 (CH), 124.2 (CH), 126.0 (CH), 127.3 (CH), 128.2 (CH), 129.3 (CH), 137.9 (C), 141.0 (C), 143.3 (C), 144.0 (C), 152.4 (C) (SI, Figure S3). HRMS ESI TOF: m/z = 344,1875 [M + H]+ (344,1870 calc. for C21H21N5) (SI, Figure S4).

3.2. 2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide (18)

Triethylamine 0.237 mL (1.7 mmol) was added to a solution of 0.2 g (0.58 mmol) of 1-(4-(dimethylamino)phenyl)-3.5-diphenylformazan in 15 mL of dry toluene, stirred for several minutes and 0.358 mL (2.9 mmol) boron trifluoride diethyl etherate was added. The reaction mixture, colored dark blue, was incubated at 90 °C for 5 h. Then, it was transferred to a separating funnel, washed with water, and the toluene layer was dried with Na2SO4. After separation of the drying agent and concentration under vacuum, the residue was purified by flash chromatography (silica, hexane–dichloromethane 10:1), the dark blue fraction containing 18. Yield 0.132 g (88%); dark green crystalline solid (bronze reflex); mp 189–190 °C. IR (KBr): ν = 3109, 3068, 3039 (Csp2-H), 2920, 2852 (Csp3-H), 1608, 1529, 1489, 1458, 1423, 1384, 1323, 1301, 1255, 1234, 1192, 1178, 1103, 1016, 817, 767 cm−1 (SI, Figure S5). 1H NMR (CDCl3, 399.78 MHz): δ = 3.08 (s, 6H, CH3), 6.70–6.74 (m, 2H, CH), 7.31–7.35 (m, 1H, CH), 7.38–7.49 (m, 5H, CH), 7.84–7.88 (m, 2H, CH), 7.92–7.96 (m, 2H, CH), 8.11–8.15 (m, 2H, CH) (SI, Figure S6). 13C NMR (CDCl3, 100.5 MHz): δ = 40.3 (CH3), 111.7 (CH), 122.7 (CH), 125.3 (CH), 125.4 (CH), 127.9 (CH), 128.5 (CH), 128.7 (CH), 128.8 (CH), 134.1 (C), 134.5 (C), 144.3 (C), 147.7 (C), 151.4 (C) (SI, Figure S7). 19F NMR (CDCl3, 376.17 MHz): δ = −144.03 (q, 1JFB = 30 Hz) (SI, Figure S8). 11B NMR (CDCl3, 128.27 MHz): δ = −1.25 (t, 1JBF = 30.5 Hz) (SI, Figure S9). HRMS ESI TOF: m/z = 392,1861 [M + H]+ (392,1853 calc. for C21H20BF2N5) (SI, Figure S10).
Crystal data for C21H20BF2N5 (M = 391.25 g/mol): monoclinic, space group P21/c, a = 17.9429(15) Å, b = 13.3212(11) Å, c = 8.1555(7) Å, α = 90°, β = 93.752(2)°, γ = 90°, V = 1945.2(3) Å3, Z = 4, T = 120 K, μ = 0.95 cm−1, Dcalc. = 1.36 g/cm3. In total, 26,190 reflections were measured, 4241 of which were unique and used in all calculations. The final R1 was 0.0438, and the wR2 was 0.1360 (all data) (SI, Tables S1–S5).

Supplementary Materials

The following supporting information can be downloaded. Figure S1: IR-spectrum of 17; Figure S2: 1H NMR of 17; Figure S3: 13C NMR of 17; Figure S4: HRMS of 17; Figure S5: IR-spectrum of 18; Figure S6: 1H NMR of 18; Figure S7: 13C NMR of 18; Figure S8: 19F NMR of 18; Figure S9: 11B NMR of 18; Figure S10: HRMS of 18; Tables S1–S5: Crystal data of 18.

Author Contributions

Conceptualization, V.V.K.; methodology, V.V.K.; software, D.N.K.; validation, V.V.K. and D.N.K.; formal analysis, D.N.K.; investigation, I.A.L. and N.A.E.; resources, I.A.L. and N.A.E.; data curation, V.V.K.; writing—original draft preparation, V.V.K. and D.N.K.; writing—review and editing, V.V.K. and D.N.K.; supervision, V.V.K.; project administration, V.V.K.; funding acquisition, V.V.K., D.N.K., and I.A.L. All authors have read and agreed to the published version of the manuscript.

Funding

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation (project no. FZEN-2020-0022).

Acknowledgments

The X-ray diffraction study was performed using the equipment (Bruker APEX DUO diffractometer) of the Center for Molecular Composition Studies of INEOS RAS, and the HRMS study was accomplished with the use of scientific equipment of the Collective Employment Centre “Ecoanalytical Centre”, Kuban State University (A. Z. Temerdashev).

Conflicts of Interest

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

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Molbank 2022 m1312 g001 550
Figure 1. Examples of various boron chelates.
Figure 1. Examples of various boron chelates.
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Molbank 2022 m1312 sch001 550
Scheme 1. Examples of preparation “boratetrazines”.
Scheme 1. Examples of preparation “boratetrazines”.
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Figure 2. Examples of various boron formazanates.
Figure 2. Examples of various boron formazanates.
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Molbank 2022 m1312 sch002 550
Scheme 2. Synthesis of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazan 17.
Scheme 2. Synthesis of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazan 17.
Molbank 2022 m1312 sch002
Molbank 2022 m1312 sch003 550
Scheme 3. Reaction of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazan 17 with boron trifluoride diethyl etherate.
Scheme 3. Reaction of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazan 17 with boron trifluoride diethyl etherate.
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Figure 3. Crystal structure of compound 18 with labeling schemes and 50% thermal ellipsoids.
Figure 3. Crystal structure of compound 18 with labeling schemes and 50% thermal ellipsoids.
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Lupanova, I.A.; Konshina, D.N.; Elkov, N.A.; Konshin, V.V. 2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide. Molbank 2022, 2022, M1312. https://doi.org/10.3390/M1312

AMA Style

Lupanova IA, Konshina DN, Elkov NA, Konshin VV. 2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide. Molbank. 2022; 2022(1):M1312. https://doi.org/10.3390/M1312

Chicago/Turabian Style

Lupanova, Ida A., Dzhamilya N. Konshina, Nikita A. Elkov, and Valery V. Konshin. 2022. "2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide" Molbank 2022, no. 1: M1312. https://doi.org/10.3390/M1312

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