Synthesis and crystal structural characterization of two new 3,5-disubstituted 4-amino-1,2,4-triazoles
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Xin He
Abstract
Two new asymmetrical 3-(p-R-phenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazoles (3a, R = CH3 and 3b, R = OCH3) were synthesized with a yield of 58% and 69%, respectively. The compounds 3a and 3b were characterized with FT-IR, 1H NMR, ESI-MS spectra, and elemental analysis. Additionally, their molecular and crystal structures were determined by single crystal X-ray analysis.
Introduction
During the past five decades, substituted 1,2,4-triazoles have aroused wide interest because of their anti-inflammatory, antitumor, fungicide, and herbicide properties [1]. Substituted 1,2,4-triazoles and their derivatives are also useful ligands in coordination chemistry due to their rich and versatile coordination modes [2–4]. In addition, some iron(II) complexes containing substituted 1,2,4-triazoles possess fascinating spin crossover properties which can be applied as molecular-based electronics, displays, and switching materials [5–10].
Recently, a series of symmetrical and asymmetrical 3,5-disubstituted 1,2,4-triazoles have been successfully prepared by our group [11–18] and others [3, 8]. However, the asymmetrical 3,5-disubstituted 4-amino-1,2,4-triazoles remain largely unexplored. As a continuation of our investigation on substituted 4-amino-1,2,4-triazoles [19, 20], in this article, we present synthesis of two new asymmetrical 3,5-disubstituted 4-amino-1,2,4-triazoles, namely 3-(p-R-phenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazoles 3a (R = CH3) and 3b (R = OCH3) (Scheme 1). Compounds 3a and 3b were characterized by FT-IR, 1H NMR, ESI-MS spectra, elemental analysis, and single crystal X-ray diffraction. For the purpose of comparison, a known homologous compound, 3c (R = Cl), is also discussed [21].
Synthesis of 3,5-disubstituted 4-amino-1,2,4-triazoles 3a–c.
Results and discussion
Synthesis of 3,4,5-trisubstituted 1,2,4-triazoles has recently been reviewed [22]. In general, there are three types of methods reported for the preparation of 3,4,5-trisubstituted 1,2,4-triazoles [23]. One of these methods was chosen for the synthesis of our target compounds – 3,5-disubstituted 4-amino-1,2,4-triazoles 3a–c. Compounds 3a,b are new and synthesis of 3c has been previously published [21].
N-(p-R-phenylcarbonyl)-N′-(2-pyridylcarbonyl)hydrazines 1a–c were obtained in a yield of 81%, 79%, and 82%, respectively, by stirring pyridine-2-carbonylhydrazine with the corresponding benzoyl chloride in anhydrous pyridine at ambient temperature [24]. Then, 1,4-dichloro-1-(2-pyridyl)-4-(p-R-phenyl)-2,3-diaza-1,3-butadienes 2a–c were obtained by stirring 1 with thionyl chloride in dried toluene with the respective yield of 68%, 69%, and 72% [25]. Finally, the cyclization reaction of 2a,b with anhydrous hydrazine conducted at 120°C for 12 h produced 3a,b with a yield of 58% and 69%, respectively. Synthesis of the known compound 3c in a 47% yield has previously been reported [21].
New compounds 3a,b were characterized by FT-IR, 1H NMR, ESI-MS, and elemental analysis. The molecular structures of 3a,b were also confirmed by X-ray crystallography (Table 1). Single crystals of 3a and 3b suitable for X-ray diffraction study were obtained upon slow concentration of ethanol solution at ambient temperature. The crystal structure of 3c has been previously published [21]. The crystal structures of 3a,b with an atom-labeling scheme are shown in Figure 1, and selected bond lengths and bond angles are listed in Table 2. The X-ray crystallography analysis indicates that both 3a and 3b crystallize in the triclinic space group P1̅, which is different from the homologous compound 3c (C2/c). The central 1,2,4-triazole in 3a is oriented at interplanar angles of 2.0(1)° and 30.2(1)° with respect to the pyridyl ring and the p-methylphenyl ring, respectively. Similarly, the central 1,2,4-triazole ring in 3b is oriented at interplanar angles of 7.1(1)° and 30.9(1)° with respect to the pyridyl ring and the p-methoxyphenyl ring, respectively (Table 3). In addition, the N atom of the pyridyl group is oriented towards the amino group on the N4 position in both 3a and 3b. This feature is similar to that of the related substituted 4-amino-1,2,4-triazoles compounds [19, 20]. The bond lengths and bond angles of 3a and 3b are similar and in normal ranges [23, 26, 27]. The hydrogen bonds, a C-H···π interaction and a non-bonding π···π interaction in these compounds are given in Table 4. These interactions stabilize the crystal packing of 3a and 3b. The crystal packing diagrams of 3a and 3b are shown in Figures 2 and 3, respectively.
Crystallographic data for 3a–c.
| Compound | 3a | 3b | 3c [21] |
|---|---|---|---|
| Empirical formula | C14 H13 N5 | C14 H13 N5 O | C13 H10 N5 Cl |
| Formula weight | 251.29 | 267.29 | 271.71 |
| Crystal system | Triclinic | Triclinic | Monoclinic |
| Space group | P1̅ | P1̅ | C2/c |
| a (Å) | 6.2709(10) | 6.183(10) | 28.68(7) |
| b (Å) | 7.0252(12) | 7.245(12) | 6.041(16) |
| c (Å) | 14.572(2) | 14.77(2) | 14.68(4) |
| α (°) | 86.277(2) | 76.816(17) | 90.00 |
| β (°) | 84.922(2) | 85.501(18) | 103.90(3) |
| γ (°) | 72.728(2) | 73.507(18) | 90.00 |
| V (Å3) | 610.09(17) | 617.7(17) | 2470(11) |
| Z | 2 | 2 | 8 |
| Dc (g⋅cm-3) | 1.368 | 1.437 | 1.462 |
| μ (mm-1) | 0.088 | 0.097 | 0.302 |
| F (000) | 264 | 280 | 1120 |
| Crystal size (mm) | 0.24 × 0.16 × 0.10 | 0.14 × 0.10 × 0.06 | 0.16 × 0.12 × 0.10 |
| θ Range | 1.40–25.00 | 1.42–25.00 | 1.46–25.00 |
| Reflections collected | 4295 | 4277 | 8203 |
| Independent reflections | 2125 [Rint = 0.0174] | 2128 [Rint = 0.0184] | 2175 [Rint = 0.0757] |
| Reflections observed [I>2σ(I)] | 1607 | 1817 | 1436 |
| Data/restraints/parameters | 2125/3/180 | 2128/4/188 | 2175/3/178 |
| Goodness-of-fit on F2 | 1.067 | 1.095 | 1.071 |
| R/wR [I>2σ(I)] | 0.0449/0.1234 | 0.0594/0.1852 | 0.0682/0.1834 |
| R/wR (all data) | 0.0624/0.1324 | 0.0675/0.1897 | 0.1027/0.1985 |
| Max., Min. Δρ (e⋅Å-3) | 0.227, -0.221 | 0.397, -0.377 | 0.801, -0.280 |
Note: data of 3c are given for comparison.
Views of 3a and 3b showing the atom-numbering scheme. Hydrogen atoms are omitted for clarity.
Selected bond lengths (Å) and angles (°) for 3a,b.
| 3a | 3b | ||
|---|---|---|---|
| N1-C5 | 1.338(2) | N1-C5 | 1.332(4) |
| N2-N3 | 1.372(2) | N2-N3 | 1.365(4) |
| N4-N5 | 1.419(2) | N4-N5 | 1.407(4) |
| C11-C14 | 1.508(3) | O1-C11 | 1.361(4) |
| N1-C1 | 1.338(2) | N1-C1 | 1.324(4) |
| C6-N2-N3 | 108.2(1) | C6-N2-N3 | 107.9(2) |
| C6-C5-N1 | 118.6(2) | C6-C5-N1 | 118.8(2) |
| C7-N4-C6 | 106.2(1) | C7-N4-C6 | 105.5(3) |
| N5-N4-C7 | 124.8(2) | N5-N4-C7 | 124.3(2) |
| C10-C11-C14 | 121.7(2) | C11-O1-C14 | 118.4(3) |
The interplanar angles (°) for 3a,b.
| Compound | Py/Trz | CH3-Ph/Trz | CH3 O-Ph/Trz |
|---|---|---|---|
| 3a | 2.0(1) | 30.2(1) | |
| 3b | 7.1(1) | 30.9(1) |
The hydrogen bonds, C-H···π and π···π interactions (Å, °) in 3a,b.
| Compound | D-H···A | d(D-H)/Å | d(H···A)/Å | d(D···A)/Å | ∠D-H···A/° |
|---|---|---|---|---|---|
| 3a | C1v-H1Av···N5 | 0.93 | 2.70 | 3.420(2) | 135 |
| C4-H4A···N2i | 0.93 | 2.82 | 3.394(2) | 121 | |
| N5-H5A···N1 | 0.89 | 2.15 | 2.908(2) | 142 | |
| N5-H5B···N2ii | 0.88 | 2.41 | 3.106(2) | 137 | |
| C14-H14C···π (C8-C13)iii | 0.96 | 2.98 | 3.656(2) | 128 | |
| π···π interaction | cent···cent (Å) | Dihedral angle (°) | |||
| π (Py) ···π (Trz)iv | 3.687(2) | 1.9 | |||
| 3b | C1viii-H1Aviii···N5 | 0.93 | 2.76 | 3.378(6) | 124 |
| C2vi-H2Avi···O1 | 0.93 | 2.62 | 3.533(6) | 168 | |
| N5-H5B···N1 | 0.85 | 2.27 | 2.902(5) | 131 | |
| C14-H14A···π (C8-C13)vii | 0.96 | 3.29 | 3.927(5) | 126 | |
Symmetry codes: (i) -x, 1-y, 2-z; (ii) 1+x, y, z; (iii) 2-x, -y, 1-z; (iv) 1-x, -y, 2-z; (v) 2-x, -y, 2-z; (vi) x, y-1, 1+z; (vii) 2-x, -1-y, 2-z; (viii) 2-x, -y, 1-z.
View of the crystal packing for 3a showing hydrogen bonds, C-H···π and π···π interactions.
View of the crystal packing for 3b showing hydrogen bonds and C-H···π interactions.
Experimental
Melting points were determined on an X-4 digital microscope melting-point apparatus (Beijing) and are uncorrected. FT-IR spectra were recorded on a Nicolet 380 FT-IR instrument using KBr disks. 1H NMR spectra were measured on a Bruker AM 500 MHz spectrometer at ambient temperature in DMSO-d6 for 1 and 2 but in CDCl3 for 3. Electrospray ionization mass spectra (ESI-MS) were recorded on an LCQ ADVANTAGE MAX mass spectrometer. The spray voltage, the capillary voltage, and the capillary temperature were 4 kV, 40 V, and 260°C, respectively. Elemental analyses were carried out with a Thermo Finnigan Flash 1112A elemental analyzer. All chemicals were of analytical grade and used as received. Toluene was freshly distilled from Na/benzophenone, whereas pyridine was distilled over NaOH. Pyridine-2-carbonylhydrazine was prepared according to a previously reported method [23].
Preparation of N-(p-R-phenylcarbonyl)-N′-(2-pyridylcarbonyl)hydrazines 1a–c
A suspension of the corresponding p-substituted benzoyl chloride (48 mmol) in anhydrous pyridine (10 mL) was added dropwise to a stirred solution of pyridine-2-carbonylhydrazine (5.49 g, 40 mmol) in dichloromethane (80 mL) at 0°C. The mixture was stirred for 8 h at ambient temperature and then poured into 80 mL of ice water. The resultant precipitate was filtered, dried in vacuo, and crystallized from anhydrous ethanol to give 1a–c as a white solid.
N-(p-Methylphenylcarbonyl)-N′-(2-pyridylcarbonyl)hydrazine (1a)
Yield 81%; mp 182–184°C; IR: 3189, 3010, 2922, 1674, 1633, 1607, 1500, 1280, 1114, 836, 743 cm-1; 1H NMR: δ 2.44 (3H, s, CH3), 7.13 (2H, d, J = 8 Hz, ArH), 7.54 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 8.01–8.05 (3H, m, PyH, ArH), 8.20 (1H, d, J = 8 Hz, PyH), 8.63 (1H, d, J = 5 Hz, PyH), 10.48 (1H, s, NH), 10.51 (1H, s, NH). Anal. Calcd for C14 H13 N3 O2: C, 65.87; H, 5.13; N, 16.46. Found: C, 65.73; H, 5.31; N, 16.67.
N-(p-Methoxyphenylcarbonyl)-N′-(2-pyridylcarbonyl)hydrazine (1b)
Yield 79%; mp 154–156°C (lit. mp 153–155°C [22]); IR: 3285, 3021, 2964, 1703, 1642, 1610, 1566, 1508, 1488, 1303, 1260, 1026, 998 cm-1; 1H NMR: δ 3.88 (3H, s, CH3), 7.19 (2H, d, J = 8 Hz, ArH), 7.65 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 8.05–8.09 (3H, m, PyH, ArH), 8.25 (1H, d, J = 8 Hz, PyH), 8.80 (1H, d, J = 5 Hz, PyH), 10.51 (1H, s, NH), 10.53 (1H, s, NH). Anal. Calcd for C14 H13 N3 O3: C, 61.99; H, 4.83; N, 15.49. Found: C, 61.82; H, 4.71; N, 15.77.
N-(p-Chlorophenylcarbonyl)-N′-(2-pyridylcarbonyl)hydrazine (1c)
Yield 82%; mp 179–181°C; IR: 3177, 3007, 1688, 1642, 1597, 1570, 1513, 1488, 1334, 1092, 1016, 844 cm-1; 1H NMR: δ 7.62 (2H, d, J = 8 Hz, ArH), 7.68 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 7.94 (2H, d, J = 8 Hz, ArH), 8.05 (2H, m, PyH), 8.72 (1H, d, J = 5 Hz, PyH), 10.63 (1H, s, NH), 10.67 (1H, s, NH). Anal. Calcd for C13 H10 N3 O2 Cl: C, 56.64; H, 3.66; N, 15.24. Found: C, 56.42; H, 3.54; N, 15.39.
Preparation of 1,4-dichloro-1-(2-pyridyl)-4-(p-R-phenyl)-2,3-diaza-1,3-butadienes 2a–c
A solution of thionyl chloride (5 mL) in anhydrous toluene (10 mL) was added dropwise to a stirred solution of 1 (16 mmol) in anhydrous toluene (50 mL). The mixture was heated under reflux for 8 h at 120°C and then the solvent was removed under reduced pressure. The residue was crystallized from ethanol to give 2 as colorless crystals.
1,4-Dichloro-1-(2-pyridyl)-4-(p-methylphenyl)-2,3-diaza-1,3-butadiene (2a)
Yield 68%; mp 156–158°C; IR: 3054, 2993, 1613, 1588, 1556, 1494, 1458, 1443, 1247, 1183, 1079, 824, 743, 728 cm-1; 1H NMR: δ 2.45 (3H, s, CH3), 7.32–7.34 (2H, d, J = 8 Hz, ArH), 7.47 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 7.85 (1H, m, PyH), 8.09 (2H, d, J = 7 Hz, ArH), 8.32 (1H, d, J = 8 Hz, PyH), 8.72 (1H, d, J = 5 Hz, PyH). Anal. Calcd for C14 H11 N3 Cl2: C, 57.55; H, 3.79; N, 14.38. Found: C, 57.31; H, 3.43; N, 14.49.
1,4-Dichloro-1-(2-pyridyl)-4-(p-methoxyphenyl)-2,3-diaza-1,3-butadiene (2b)
Yield 69%; mp 152–154°C; IR: 3052, 2978, 1615, 1585, 1498, 1458, 1443, 1268, 1176, 1085, 1019, 832, 790, 741 cm-1; 1H NMR: δ 3.85 (3H, s, CH3), 7.02 (2H, d, J = 8 Hz, ArH), 7.45 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 7.83 (1H, m, PyH), 8.14 (2H, d, J = 8 Hz, ArH), 8.31 (1H, d, J = 8 Hz, PyH), 8.61 (1H, d, J = 5 Hz, PyH). Anal. Calcd for C14 H11 N3 Cl2 O: C, 54.57; H, 3.60; N, 13.64. Found: C, 54.36; H, 3.45; N, 13.41.
1,4-Dichloro-1-(2-pyridyl)-4-(p-chlorophenyl)-2,3-diaza-1,3-butadiene (2c)
Yield 72%; mp 146–148°C; IR: 1605, 1586, 1553, 1479, 1463, 1442, 1275, 1151, 1090, 835, 794, 731 cm-1; 1H NMR: δ 7.45 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 7.50 (2H, d, J = 8 Hz, ArH), 7.92 (1H, m, PyH), 8.16 (2H, d, J = 8 Hz, ArH), 8.32 (1H, d, J = 8 Hz, PyH), 8.82 (1H, d, J = 5 Hz, PyH). Anal. Calcd for C13 H8 N3 Cl3: C, 49.95; H, 2.58; N, 13.44. Found: C, 49.66; H, 2.32; N, 13.68.
Preparation of 3-(p-R-phenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazoles 3a–c
A mixture of 2 (2 mmol) and anhydrous hydrazine (2 mL) was sealed in a 25 mL Teflon-lined stainless steel reactor and heated for 12 h at 120°C and then cooled to ambient temperature. The precipitate was filtered, washed with deionized water, and crystallized from anhydrous ethanol to give 3 as colorless crystals.
3-(p-Methylphenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazole (3a)
Yield 58%; mp 205–207°C; IR: 3345, 3272, 3193, 1640, 1591, 1472, 1422, 1284, 1151, 1034, 993, 961, 818, 786, 728, 696, 583 cm-1; 1H NMR: δ 2.42 (3H, s, CH3), 6.45 (2H, br, NH2), 7.30 (2H, d, J = 9 Hz, ArH), 7.36 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 7.85 (1H, m, PyH), 8.08 (2H, d, J = 9 Hz, ArH), 8.36 (1H, d, J = 7 Hz, PyH), 8.62 (1H, d, J = 5 Hz, PyH); ESI-MS: m/z 252.25 (M+H)+. Anal. Calcd for C14 H13 N5: C, 66.92; H, 5.21; N, 27.87. Found: C, 66.76; H, 5.05; N, 27.99.
3-(p-Methoxyphenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazole (3b)
Yield 69%; mp 194–195°C; IR: 3342, 3278, 3157, 2993, 2833, 1611, 1582, 1488, 1441, 1247, 1188, 1035, 972, 840, 737, 696, 594 cm-1; 1H NMR: δ 3.86 (3H, s, CH3), 6.44 (2H, br, NH2), 6.99 (2H, d, J = 9 Hz, ArH), 7.35 (1H, dd, J1 = 5 Hz, J2 = 2 Hz, PyH), 7.84 (1H, m, PyH), 8.14 (2H, d, J = 9 Hz, ArH), 8.32 (1H, d, J = 7 Hz, PyH), 8.61 (1H, d, J = 5 Hz, PyH); ESI-MS: m/z 268.3 (M+H)+. Anal. Calcd for C14 H13 N5 O: C, 62.91; H, 4.90; N, 26.20. Found: C, 62.74; H, 4.78; N, 26.31.
3-(p-Chlorophenyl)-4-amino-5-(2-pyridyl)-1,2,4-triazole (3c)
See reference [21].
Single-crystal X-ray diffraction analysis of 3a and 3b
The single crystals of 3a and 3b were selected for lattice parameter determination and collection of intensity data at 296 K on a Bruker SMART CCD diffractometer with a detector distance of 5 cm and frame exposure time of 10 s using a graphite-monochromated Mo-Kα (λ = 0.71073 Å) radiation. The structures were solved by direct methods and refined on F2 by full-matrix least squares procedures using SHELXTL software [28]. All non-hydrogen atoms were anisotropically refined. The H atoms were placed on calculated positions (C-H 0.96 Å) and assigned isotropic thermal parameters riding on their parent atoms; the H atoms of -NH2 were located from difference Fourier maps and refined isotropically. Details on crystal data of 3a and 3b are summarized in Table 1.
CCDC 983076 (3a) and 983077 (3b) contain the supplementary crystallographic data for this article. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
Acknowledgments
This work was funded by the National Natural Science Foundation of China (nos. 20771059, 21171093).
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- A novel synthetic approach to 11-substituted dibenzo[b,f][1,4]oxazepines
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- Synthesis and crystal structural characterization of two new 3,5-disubstituted 4-amino-1,2,4-triazoles
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- Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones
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Articles in the same Issue
- Frontmatter
- Preliminary Communication
- A novel synthetic approach to 11-substituted dibenzo[b,f][1,4]oxazepines
- Research Articles
- Cyclopropyl aziridines: solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene
- Synthesis and crystal structural characterization of two new 3,5-disubstituted 4-amino-1,2,4-triazoles
- A facile synthesis of 7,12-dihydro-1,3,6,7,12-pentaazapleiadenes by domino reaction
- New derivatives of 4,6-dimethylisoxazolo[3,4-b] pyridin-3(1H)-one: synthesis, tautomerism, electronic structure and antibacterial activity
- Synthesis and antimicrobial evaluation of purine substituted N-acyl-α-carboxamides via the Ugi four-component reaction
- Facile synthesis of substituted dihydro-1H-pyrazolo[3,4-d]thiazoles through enaminones of 4-thiazolidinones
- Multi-component synthesis of 1,2-diphenyl-2-[2-(5-aryl-6H-1,3,4-thiadiazin-2-yl)hydrazono]ethanone
- Ab initio study of mechanism of forming a spiro-Si-heterocyclic compound involving Ge from (CH3)2Ge=Si: and formaldehyde
