CN101544639A - A method for preparing pyridine derivatize compounds - Google Patents
A method for preparing pyridine derivatize compounds Download PDFInfo
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- CN101544639A CN101544639A CN200910114038A CN200910114038A CN101544639A CN 101544639 A CN101544639 A CN 101544639A CN 200910114038 A CN200910114038 A CN 200910114038A CN 200910114038 A CN200910114038 A CN 200910114038A CN 101544639 A CN101544639 A CN 101544639A
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Abstract
The invention provides a method for preparing pyridine derivatize compounds, whose name is 4, 8, 10-trimethyl-2-(3, 5-dimethyl pyrazole )-pyridine [2', 3':3, 4 ]pyrazole [1, 5-a] pyrimidine. The preparing method is indicated taking 3-cyano -4-methyl -2, 6-dichloropyridine as raw charge, copper as energizing agent and reacting with hydrazine hydrate, then getting 4-methyl -6-hydrazino -2H-pyrazole [3, 4-b]-pyridine -3-amine with the rate of production 87%, 4-methyl-6-hydrazino -2Hpyrazole [3, 4-b]-pyridine -3-amine reacting with acetylacetone, acetic acid as energizing agent, then getting the product 4, 8, 10- trimethyl -2-(3, 5-dimethyl pyrazole )-pyridine [2', 3 ' : 3, 4 ] pyrazole [ 1, 5 - a ] pyrimidine] with the rate of production 52%. The product has extensive latent use in luminescent material, medicine, pesticides material, etc.
Description
Technical field
The invention belongs to a kind of pyridine derivative compound and preparation method thereof technical field.
Background technology
4,8,10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine is a kind of new pyridine derivative compound, and up to the present this material and preparation method thereof, does not also have bibliographical information.
Summary of the invention
The purpose of this invention is to provide a kind of new pyridine derivative compound and preparation method thereof.This compound is a kind of industrial chemicals, and purposes is widely arranged.Especially the application on fluorescent material, more outstanding, create a kind of advanced luminescent material, be a kind of luminescent material of using future that has very much; Simultaneously, it also is a kind of novel chelating agents, with the synthetic metal complexes of metal ion.
The technical scheme that the present invention solves the problems of the technologies described above is as follows:
1. pyridine derivative compound, the chemical name of this pyridine derivative compound is 4,8,10-trimethylammonium-2-(3,5-two basic pyrazoles)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine;
Structural formula is
Molecular formula is C
17H
18N
6
Physico-chemical property: outward appearance is light yellow needle-like crystal, and 105～106 ℃ of fusing points are tasteless, are soluble in tetrahydrofuran (THF), toluene, ethyl acetate, dioxane, are insoluble to N, and dinethylformamide and sherwood oil are slightly soluble in methyl alcohol, ethanol and acetone.
2. the preparation method of a pyridine derivative compound
Reaction equation:
Preparation process is as follows successively:
1) preparation of compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine "
With 3-cyano group-4-methyl-2,6-dichloropyridine and hydrazine hydrate are raw material, and copper is made catalyzer, and catalyst levels is 3-cyano group-4-methyl-2, and about 1% of 6-dichloropyridine amount stirs, and oil bath backflow 5h after reaction finishes, gets yellow solution; Through cooling, suction filtration, the gained yellow powder is used ethyl alcohol recrystallization, obtains yellow needle, i.e. compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine ";
2) preparation of compound 3 " 4,8,10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine ",
With 1) compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine " and the methyl ethyl diketone that obtain be raw material, and acetate is made catalyzer, and catalyst levels is about 1% of 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine amount; Stir, oil bath backflow 5h after reaction finishes, gets pale yellow solution, cooling, suction filtration is used ethyl alcohol recrystallization, gets light yellow needle-like crystal, is product 4,8 of the present invention, 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine ";
3) the present invention 4,8, the affirmation of 10-trimethylammonium-2-(3,5-two basic pyrazoles)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine
With make 4,8,10-trimethylammonium-2-(3,5-two basic pyrazoles)-light yellow needle-like crystal of pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine is dissolved in the tetrahydrofuran (THF), adds suitable quantity of water, can obtain colorless prismatic crystal in the slow volatilization of room temperature.By section, choose the monocrystalline of 0.49mm * 0.32mm * 0.29mm, on Bruker SmartAPEXIICCD diffractometer, with through the Mo Ka of the graphite monochromatization device monochromatization (ray of λ=0.071073nm), scan in ω-θ mode, sweep limit is 1.42 °＜θ＜25.01 °, under 298 (2) K, collect 7759 of point diffractions altogether, wherein 2727 is independent point diffraction, intensity data is found the solution by direct method and Fourier synthesis method through Lp and experience absorption correction, through the complete matrix method of least squares F2 is revised.Structural analysis is finished with the SHELXL-97 software package.Crystal structure analysis shows that the molecular formula of compound 3 is C
17H
19N
6, relative molecular mass is 307.38g/mL, crystal is an oblique system, P2
1/ c spacer, unit cell parameters is: a=8.0338 (9) nm, b=28.618 (3) nm, c=7.2688 (8) nm, a=γ=90.00, β=111.051 (2), V=1559.6 (3) nm
3, Dc=1.309mg/m
3, μ=0.083mm
-1, F (000)=652, Z=4.
1. the present invention 4,8, the purposes of 10-trimethylammonium-2-(3,5-two basic pyrazoles)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine.
4,8,10-trimethylammonium-2-(3,5-two basic pyrazoles)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine is a kind of industrial chemicals, at fluorescent material, there is purposes widely aspects such as medicine, agricultural chemicals, material, and the especially application on fluorescent material is more outstanding, creating a kind of advanced luminescent material, is a kind of luminescent material of using future that has very much.It also is a kind of novel chelating agents, with the synthetic metal complexes of metal ion.
The invention has the beneficial effects as follows provides a kind of new pyridine derivative compound 4,8,10-trimethylammonium-2-(3,5-two basic pyrazoles)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine and preparation method thereof.It is a kind of industrial chemicals, and purposes is widely arranged, and the especially application on fluorescent material is more outstanding, creates a kind of advanced luminescent material, is a kind of luminescent material of using future that has very much.It also is a kind of novel chelating agents, with the synthetic metal complexes of metal ion.
Description of drawings
Fig. 1 is the infrared spectrum spectrogram of 4-methyl-6-diazanyl-2H-pyrazoles [3, the 4-b]-pyridine-3-amine of intermediate product of the present invention.
Fig. 2 is 4,8 of a final product of the present invention, the infrared spectrogram of 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine.
Fig. 3 is a raw material 3-cyano group-2 of the present invention, the ultraviolet spectrogram of 6-two chloro-4-picolines.
Fig. 4 is a final product 4,8 of the present invention, the ultraviolet spectrogram of 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidines (final product).
Fig. 5 is the comparison diagram of raw material of the present invention and final product ultraviolet spectrogram.
Fig. 6 is a final product nucleus magnetic resonance of the present invention
1H spectrum mensuration is also carried out structural analysis figure.
Fig. 7 is a final product nucleus magnetic resonance of the present invention
13C spectrum mensuration is also carried out structural analysis figure.
Fig. 8 is molecule steric configuration figure of the present invention.
Fig. 9 is a structure cell accumulation graph of the present invention.
Figure 10 is the weak hydrogen bond action figure in the packing of molecules of the present invention.
Embodiment
Below in conjunction with accompanying drawing and preparation method embodiment the present invention is further described:
Embodiment 1:
1. the preparation of compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine ".
Get 3g (0.016mol) 3-cyano group-4-methyl-2, the 6-dichloropyridine adds the 10mg copper powder in the round-bottomed flask of 50mL, slowly add the hydrazine hydrate of 10mL85% (0.206mol) again, 100～120 ℃ of 3～8h that reflux of oil bath.After reaction finishes, get yellow solution, cooling places refrigerator and cooled to freeze a night reaction solution.Suction filtration, gained yellow powder ethyl alcohol recrystallization gets the yellow needle of 2.48g, productive rate 87%.Fusing point: 235～236 ℃; IR (KBr) v:3397.7,332707,3330.2,3181.8,2994.8,2925.4,2830.4,1621.7,1487.9,1468.3,1403.5,1323.2,1218.8,912.1,830.7,816.1,734.6cm
-1Anal.Calcd for C
7H
10N
6: C47.18, H5.66, N47.16; Found C47.16, H5.69, N47.15.
2. the preparation of compound 3 " 4,8,10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine ".
48g (0.014mol) places the round-bottomed flask of 50mL with 1. compounds that obtain 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3; 4-b]-pyridine-3-amine ", to wherein adding 10mL (0.098mol) methyl ethyl diketone and 2mL (0.035mol) acetate, stir, 100～120 ℃ of 3～8h that reflux of oil bath, after reaction finishes, get pale yellow solution, cooling, reaction solution is refrigerated a night, suction filtration is used ethyl alcohol recrystallization, gets light yellow needle-like crystal, dry, weigh, get the light yellow needle of 2.55g, productive rate: 52%.Fusing point: 105～106 ℃;
1H NMR (DMSO, 300MHz) δ: 7.3 (s, 1H, CH-pyridines), 6.9 (s, 1H, CH-pyrimidines), 5.9 (s, 1H, CH-pyrazoles), 2.80～2.33 (m, 15H, CH
3); IR (KBr) v:3022.2,2977.6,2923.8,2360.3,2339.4,1630.3,1575.9,1443.3,1384.3,1366.5cm
-1Anal.Calcd for C17H18N6:C66.65, H5.92, N27.43; Found C66.62, H5.93, N27.45.
The pure product 0.3g that makes is dissolved in the 20mL tetrahydrofuran (THF), adds 5mL water, room temperature is slowly volatilized and can be obtained colorless prismatic crystal in 10 days.By section, choose the monocrystalline of 0.49mm * 0.32mm * 0.29mm, on Bruker Smart APEXIICCD diffractometer, use Mo K α through the monochromatization of the graphite monochromatization device (ray of λ=0.071073nm), scan in ω-θ mode, sweep limit is 1.42 °＜θ＜25.01 °.Under 298 (2) K, collect 7759 of point diffractions altogether, wherein 2727 is independent point diffraction.Intensity data is found the solution by direct method and Fourier synthesis method through Lp and experience absorption correction, through the complete matrix method of least squares F2 is revised.Structural analysis is finished with the SHELXL-97 software package.Crystal structure analysis shows that the molecular formula of compound 3 is C
17H
19N
6, relative molecular mass is 307.38g/mL, crystal is an oblique system, P2
1/ c spacer, unit cell parameters is: a=8.0338 (9) nm, b=28.618 (3) nm, c=7.2688 (8) nm, α=γ=90.00, β=111.051 (2), V=1559.6 (3) nm
3, Dc=1.309mg/m
3, μ=0.083mm
-1, F (000)=652, Z=4.
Accompanying drawing is analyzed
(1) Infrared spectroscopy:
In preparation 4,8, in the process of 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine, the infrared spectrum of intermediate product 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine as shown in Figure 1.The spectrum analysis of 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine (intermediate product): at 3397cm
-1There is the stretching vibration absorption peak of N-H in the pyrazoles ring at the place, at 3300～3181cm
-1There is amino N-H stretching vibration absorption peak at the place, at 2839～3065cm
-1There is the stretching vibration absorption peak of methyl at the place, at 1621cm
-1And 1600cm
-1There is the stretching vibration absorption peak of conjugation intra-annular C=N at the place, at 1323～1487cm
-1There is the flexural vibration absorption peak of methyl at the place.
The present invention 4,8, the infrared spectrogram of 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine as shown in Figure 2, spectrum analysis: at 2923～2977cm
-1There is the stretching vibration absorption peak of methyl at the place, at 2360～2339cm
-1There is CO at the place
2Absorption peak is at 1630～1575cm
-1There are conjugation intra-annular C=N, C=C stretching vibration absorption peak in the place, at 1343～1443cm
-1There is the flexural vibration absorption peak of methyl at the place, can infer tentatively that the amino of intermediate product reacts from spectrogram.
(2) ultraviolet spectral analysis:
For whether the conjugated system of further understanding the material that generates changes, we have also carried out ultraviolet spectral analysis.If it is big that conjugated system becomes, then the absorption peak of the material of Sheng Chenging can become greatly, and red shift can take place in the position at peak.
Fig. 3 is the present invention 4,8,10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] the raw material 3-cyano group-2 of pyrimidine, the ultraviolet spectrogram of 6-two chloro-4-picolines, we are as can be seen from Fig. 3, at 200～225nm and 225～250nm place absorption peak is arranged, the maximum absorption degree is respectively to exceed 1.5 and 0.75.Fig. 4 is 4,8, and the ultraviolet spectrogram of 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidines (final product) from Fig. 4 as seen, has absorption peak at 275～325nm place, and the maximum absorption degree is 1.25.Fig. 5 is the comparison diagram of raw material and final product ultraviolet spectrogram, red shift can take place by the position that relatively can know the peak by inference, the conjugated system that generates final product is not than big (because make the concentration of intermediate product and product the same when measuring, so the size of can not dividing conjugated system from their height at peak) of raw material.
(3) nucleus magnetic resonance
1The H spectrum,
13The C spectrum is analyzed final product:
The final product nucleus magnetic resonance
1The H spectrum is measured and is carried out structural analysis, as shown in Figure 6.
The final product nucleus magnetic resonance
13The C spectrum is measured and is carried out structural analysis, as shown in Figure 7.
The structural analysis of Fig. 6 and Fig. 7 is identical, has confirmed the structure of final product such as the structural formula among Fig. 6, Fig. 7.
The fractional coordinates (* 10 of part non-hydrogen atom in table 1 compound 3
4) and thermal parameter (* 10
4Nm
2)
The part bond distance (10 of table 2 compound 3
-1Nm) and bond angle (°)
Crystal structure analysis shows that the crystal of compound 3 is an oblique system, and spacer is P2
1/ c, unit cell parameters is: a=8.0338 (9) nm, b=28.618 (3) nm, c=7.2688 (8) nm, α=γ=90.00, β=111.051 (2), V=1559.6 (3) nm
3, Dc=1.309g/cm
3, μ=0.083mm
-1, F (000)=652, Z=4, R
1=0.0566, wR
2=0.1320.From monomolecular steric configuration Fig. 8 as can be seen, three shared planes of ring, other pyrazoles ring and this planar angle only are 4.2 °, four cyclic groups originally are in same plane, intramolecularly does not have hydrogen bond or weak bond to link to each other, and from accumulation graph 9, can see, intermolecularly be connected with weak bond, form laminate structure.In with one deck, methyl on pyrimidine and the pyridine and the nitrogen C7 in the pyrazoles ... N2 couples together molecule by weak hydrogen bond, and between layer and the layer by hydrogen bond C5 a little less than in the heterocycle other ... C9, C5 ... C10, C3 ... C6, C6 ... C2 couples together, as shown in Figure 10, angle between layer and the layer is 0.88 °, and layer is substantially parallel with layer.
Claims (2)
1. pyridine derivative compound is characterized in that:
1) chemical name of this pyridine derivative compound is 4,8,10-trimethylammonium-2-(3,5-two basic pyrazoles)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine;
2) structural formula is
Molecular formula is C
17H
18N
6
3) physico-chemical property: outward appearance is light yellow needle-like crystal, and 105～106 ℃ of fusing points are tasteless, are soluble in tetrahydrofuran (THF), toluene, ethyl acetate, dioxane, are insoluble to N, and dinethylformamide and sherwood oil are slightly soluble in methyl alcohol, ethanol and acetone.
2. the preparation method of a pyridine derivative compound is characterized in that,
Reaction equation:
Preparation process is as follows successively:
1) preparation of compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine "
With 3-cyano group-4-methyl-2,6-dichloropyridine and hydrazine hydrate are raw material, and copper is made catalyzer, and catalyst levels is 3-cyano group-4-methyl-2, and about 0.5% of 6-dichloropyridine amount stirs, and oil bath backflow 5h after reaction finishes, gets yellow solution; Through cooling, suction filtration, the gained yellow powder is used ethyl alcohol recrystallization, obtains yellow needle, i.e. compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine ";
2) preparation of compound 3 " 4,8,10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine ",
With 1) compound 2 " 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine " and the methyl ethyl diketone that obtain be raw material, and acetate is made catalyzer, and catalyst levels is about 1% of 4-methyl-6-diazanyl-2H-pyrazoles [3,4-b]-pyridine-3-amine amount; Stir, oil bath backflow 5h after reaction finishes, gets pale yellow solution, cooling, suction filtration is used ethyl alcohol recrystallization, gets light yellow needle-like crystal, is product 4,8 of the present invention, 10-trimethylammonium-2-(3)-pyridine [2 ', 3 ': 3,4] pyrazoles [1,5-a] pyrimidine ".
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329316A (en) * | 2017-12-29 | 2018-07-27 | 广西师范学院 | A kind of biological fluorescent labeling and preparation method thereof of detection nickel ion |
-
2009
- 2009-05-07 CN CN200910114038A patent/CN101544639A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108329316A (en) * | 2017-12-29 | 2018-07-27 | 广西师范学院 | A kind of biological fluorescent labeling and preparation method thereof of detection nickel ion |
| CN108329316B (en) * | 2017-12-29 | 2019-10-22 | 广西师范学院 | A kind of biological fluorescent labeling and preparation method thereof detecting nickel ion |
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