CN103387543A - Synthesis method of tetrahydropyrazolone derivative - Google Patents
Synthesis method of tetrahydropyrazolone derivative Download PDFInfo
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- BISBRYMELPZPKW-UHFFFAOYSA-N CC(C)(Cc(c1c2-c3cc(Cl)c(C)cc3)n[n]2-c(cc2)ccc2Cl)CC1=O Chemical compound CC(C)(Cc(c1c2-c3cc(Cl)c(C)cc3)n[n]2-c(cc2)ccc2Cl)CC1=O BISBRYMELPZPKW-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a synthesis method of a tetrahydropyrazolone derivative. The structural formula of the tetrahydropyrazolone derivative is shown by a formula (4a) in a reaction equation 1. The synthesis method comprises the following steps of: by taking aromatic aldehyde shown by a structural formula (1a) in the reaction equation 1, 5,5-dimethylcyclohexanedione shown by a formula (2a) and phenylhydrazine hydrochloride shown by a formula (3a) as substrates and taking an ionic liquid shown by a formula (b) as a catalyst and ethanol as a reaction solvent, performing microwave reaction at 70-80 DEG C for 15-25 minutes; after the reaction, evaporating the solvent, washing solids with water and filtering; and drying filter cakes, and then re-crystallizing by use of ethanol to obtain the tetrahydropyrazolone derivative. The method disclosed by the invention has the characteristics of mild reaction conditions, simple and convenient operation, short reaction time, recyclable ionic liquid, environment-friendly synthesis process, high yield and purity and the like. The reaction equation is shown in the specification.
Description
(1) technical field
The present invention relates to a kind of synthetic method of tetrahydro-pyrazole ketone derivatives.
(2) background technology
Tetrahydro-pyrazole ketone is a compound with extensive physiology and pharmacologically active.The compound that contains pyrazoles and pyrazolone structure has weeding, anti-infective, anticancer and tuberculosis effect.Tetrahydro-pyrazole ketone structure has similar structures such as the structural formula 1 of heat shock protein inhibitors (HSP-90) and anti-breast cancer cell-proliferation activity.Simultaneously, tetrahydro-pyrazole also has tubercule bacillus inhibitor similar structures unit (MTB) as structural formula 2.A thereby synthetic focus that has become research of tetrahydro-pyrazole ketone derivatives.Wherein the synthetic method of report only has Rao V.K. to synthesize tetrahydro-pyrazole ketone derivatives (Bioorg.Med.Chem.Lett.2012 at imidazole ion liquid take the trifluoroacetic acid ytterbium as catalyzer under 100 ℃, 22:410-414), the characteristics of its reaction are to use rare metal to be catalyzer, carry out in ionic liquid and heating, reaction times is longer, catalyzer is not only expensive, and is difficult to recycle, and can bring to a certain degree pollution to environment.Not only toxicity is large for the aryl hydrazine raw material of its use simultaneously, price, and is difficult for preserving.Therefore, simple and tetrahydro-pyrazole ketone derivatives synthetic method high-efficiency environment friendly of invention seems particularly important.
(3) summary of the invention
For solve existing prepare in tetrahydro-pyrazole ketone derivatives technology catalyzer expensive, be difficult to reclaim and the unfavorable factors such as long reaction time, advocate simultaneously a kind of more green, synthetic theory efficiently, the objective of the invention is to disclose a kind of take the disulfonic acid type ionic liquid as catalyzer, be reaction solvent at ethanol, the synthetic method of the tetrahydro-pyrazole ketone derivatives under advancing at the microwave place.The method reaction conditions is gentle, and easy and simple to handle, the reaction times is short, and ionic liquid can be recycled, and building-up process is environmentally friendly, productive rate and purity high.
For reaching the purpose of invention, the technical solution used in the present invention is as follows:
a kind of synthetic method of tetrahydro-pyrazole ketone derivatives, the structural formula of described tetrahydro-pyrazole ketone derivatives is as shown in the formula in reaction equation 1 (4a), described synthetic method is with the aromatic aldehyde as shown in the structural formula as in reaction equation 1 (1a), shown in formula (2a) 5, aryl hydrazine hydrochloride shown in 5-dimedone and formula (3a) is substrate, take the ionic liquid shown in formula (b) as catalyzer, take ethanol as reaction solvent, in 70～80 ℃ of lower microwave reactions 15～25 minutes, after reaction finishes, steam solvent, solid washes filtration with water, filtration cakes torrefaction namely obtains described tetrahydro-pyrazole ketone derivatives by ethyl alcohol recrystallization.
Reaction equation is as follows:
R in the said structure formula
1For hydrogen, methyl, chlorine; R
2For hydrogen, chlorine, nitro.
Aromatic aldehyde of the present invention, 5, the amount of substance of 5-dimedone and aryl hydrazine hydrochloride are than being 1:1:1, and described ionic liquid is (0.02～0.08) with aromatic aldehyde amount of substance ratio: 1.
The microwave reaction time of the present invention is 15～25 minutes.
Microwave reaction temperature of the present invention is 70～80 ℃, and microwave input power is 400W.
Reaction of the present invention is distilled away ethanol after finishing, and obtain solid product and wash with water, but after the distillation of water-soluble ionic liquid dewaters, direct circulation uses.
Reaction of the present invention is take ethanol as reaction solvent, and microwave promotes lower tetrahydrobiopterin synthesis pyrazolone derivative, and its principal character is embodied in following aspect:
1) the aryl hydrazine hydrochloride replaces the phenylhydrazine raw material of bibliographical information, and not only price has certain advantage, and aryl hydrazine hydrochloride toxicity is low, is convenient to storage and transportation;
2) take the disulfonic acid type ionic liquid as catalyzer, avoid using the rare metal catalyzer, not only reduce environmental pollution, but also can reuse;
3) microwave promotes reaction, and the reaction times is short, and is easy and simple to handle, and yield and product purity are high.
To sum up, the synthetic method of a kind of tetrahydro-pyrazole ketone derivatives of the present invention is a kind of green synthesis method, is suitable for suitability for industrialized production.
(4) specific implementation method
Below in conjunction with specific embodiment, the present invention is further described, but protection scope of the present invention is not limited in this.
Embodiment 1
With phenyl aldehyde (25mmol), 5,5-dimedone (25mmol), hydrazinobenzene hydrochloride salt (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join successively in this reaction vessel, reaction vessel is placed in microwave reactor, and in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, remaining solid 20mL water washing, filter, filter cake obtains product with ethyl alcohol recrystallization, yield 85%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.50 (s, 1H), 7.38 – 7.31 (m, 6H), 7.18 – 7.25 (m, 2H), 6.94 (d, J=8.0Hz, 1H), 2.82 (s, 2H), 2.43 (s, 2H), 1.17 (s, 6H);
13C NMR (100MHz, CDCl
3): δ 28.47,34.85, and 53.73,105.01,116.21,124.19,127.67,129.85,130.21,130.27,132.09,133.13,138.38,143.46,156.96,193.38.
Embodiment 2:
With p-tolyl aldehyde (25mmol), 5,5-dimedone (25mmol), hydrazinobenzene hydrochloride salt (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join successively in this reaction vessel, reaction vessel is placed in microwave reactor, and in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, remaining solid 20mL water washing, filter, filter cake obtains product with ethyl alcohol recrystallization, yield 87%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.44 – 7.35 (m, 3H), 7.35-7.28 (m, 2H), 7.17 (d, J=8.0Hz, 2H), 6.90 (d, J=4.0Hz, 2H), 2.85 (s, 2H), (2.41 s, 2H), 2.23 (s, 3H), 1.20 (s, 6H);
13CNMR (100MHz, CDCl
3): δ 19.75,28.44, and 34.87,37.13,53.70,123.49,126.01,126.25,128.71,130.97,131.68,134.69,135.70,136.48,137.68,156.73,193.55.
Embodiment 3:
With 4-chloro-benzaldehyde (25mmol), 5,5-dimedone (25mmol), hydrazinobenzene hydrochloride salt (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join successively in this reaction vessel, reaction vessel is placed in microwave reactor, and in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, remaining solid 20mL water washing, filter, filter cake obtains product with ethyl alcohol recrystallization, yield 88%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.50-7.43 (m, 2H), 7.38 – 7.31 (m, 4H), 7.18 – 7.25 (m, 2H), 6.93 (d, J=8.0Hz, 1H), 2.81 (s, 2H), 2.43 (s, 2H), 1.18 (s, 6H);
13C NMR (100MHz, CDCl
3): δ 28.46,34.86, and 53.63,105.05,116.22,125.19,127.67,129.87,130.21,130.27,132.09,133.13,138.38,144.46,156.97,193.38.
Embodiment 4:
Will be to 3,4-dichlorobenzaldehyde (25mmol), 5,5-dimedone (25mmol), hydrazinobenzene hydrochloride salt (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join in this reaction vessel successively, and reaction vessel is placed in microwave reactor, in 75 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, and remaining solid 20mL water washing is filtered, filter cake obtains product with ethyl alcohol recrystallization, yield 87%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.50 (s, 1H), 7.38 – 7.31 (m, 6H), 7.18 – 7.25 (m, 2H), 6.94 (d, J=8.0Hz, 1H), 2.82 (s, 2H), 2.43 (s, 2H), 1.17 (s, 6H);
13C NMR (100MHz, CDCl
3): δ 28.47,34.85, and 53.73,105.01,116.21,124.19,127.67,129.85,130.21,130.27,132.09,133.13,138.38,143.46,156.96,193.38.
Embodiment 5:
With phenyl aldehyde (25mmol), 5,5-dimedone (25mmol), paranitrophenylhydrazine hydrochloride (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join successively in this reaction vessel, reaction vessel is placed in microwave reactor, and in 75 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, remaining solid 20mL water washing, filter, filter cake obtains product with ethyl alcohol recrystallization, yield 85%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.50 (s, 1H), 7.38 – 7.31 (m, 6H), 7.18 – 7.25 (m, 2H), 6.94 (d, J=8.0Hz, 1H), 2.82 (s, 2H), 2.43 (s, 2H), 1.17 (s, 6H);
13C NMR (100MHz, CDCl
3): δ 28.47,34.85, and 53.73,105.01,116.21,124.19,127.67,129.85,130.21,130.27,132.09,133.13,138.38,143.46,156.96,193.38.
Embodiment 6:
With 4-chloro-benzaldehyde (25mmol), 5,5-dimedone (25mmol), paranitrophenylhydrazine hydrochloride (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join successively in this reaction vessel, reaction vessel is placed in microwave reactor, and in 75 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, remaining solid 20mL water washing, filter, filter cake obtains product with ethyl alcohol recrystallization, yield 90%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=8.22 (d, J=2.51Hz, 3H), 7.55 – 7.53 (d, J=2.48Hz, 3H), 7.33 (s, 1H), 6.95 (d, J=8.0Hz, 1H), 2.84 (s, 2H), 2.45 (s, 2H), 1.17 (s, 6H);
13C NMR (100MHz, CDCl
3): δ 28.44,34.94, and 37.07,53.62,116.92,123.55,124.18,127.23,130.78,131.44,133.00,134.18,137.78,140.70,148.26,157.29,193.46.
Embodiment 7:
With 3,4-dichlorobenzaldehyde (25mmol), 5,5-dimedone (25mmol), paranitrophenylhydrazine hydrochloride (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join in this reaction vessel successively, and reaction vessel is placed in microwave reactor, in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, and remaining solid 20mL water washing is filtered, filter cake obtains product with ethyl alcohol recrystallization, yield 92%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=8.24 (d, J=2.51Hz, 2H, C3-Ar-H), 7.56 – 7.54 (d, J=2.48Hz, 3H), 7.32 (s, 1H), 6.91 (d, J=8.0Hz, 1H), 2.84 (s, 2H), 2.45 (s, 2H), 1.18 (s, 6H);
13CNMR (100MHz, CDCl
3): δ 28.43,34.95, and 37.04,53.62,116.90,123.55,124.18,127.21,130.77,131.44,133.00,134.08,137.68,140.69,148.25,157.27,193.49.
Embodiment 8:
With 3,4-dichlorobenzaldehyde (25mmol), 5,5-dimedone (25mmol), p-hydrochloride (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join in this reaction vessel successively, and reaction vessel is placed in microwave reactor, in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, and remaining solid 20mL water washing is filtered, filter cake obtains product with ethyl alcohol recrystallization, yield 91%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.45 – 7.34 (m, 3H), 7.36 (d, J=3.0Hz, 1H), 7.17 (d, J=8.0Hz, 2H), 6.91 (d, J=4.0Hz, 1H), 2.86 (s, 2H), 2.42 (s, 2H), 1.21 (s, 6H);
13C NMR (100MHz, CDCl
3): δ 19.76,28.45, and 34.87,37.13,53.70,123.49,126.05,126.25,128.72,130.97,131.68,134.70,135.71,136.48,137.68,156.75,193.56.
Embodiment 9:
With 3,4-dichlorobenzaldehyde (25mmol), 5,5-dimedone (25mmol), 3-chlorophenyl hydrazine hydrochloride (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join in this reaction vessel successively, and reaction vessel is placed in microwave reactor, in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, and remaining solid 20mL water washing is filtered, filter cake obtains product with ethyl alcohol recrystallization, yield 88%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.53 (d, J=4.0Hz, 1H), 7.33 (d, J=8.0Hz, 1H), 6.97 – 6.94 (m, 4H), 6.85 (d, J=4.0Hz, 1H), 3.77 (s, 3H), 2.81 (s, 2H), 2.42 (s, 2H), 1.17 (s, 6H, C (CH
3)
2);
13C NMR (100MHz, CDCl
3): δ 28.47,34.84, and 37.17,53.77,55.39,115.71,115.80,116.29,122.49,124.10,126.97,128.86,129.49,130.36,132.04,138.44,143.22,156.92,159.30,193.33.
Embodiment 10:
With 3-chloro-4-tolyl aldehyde (25mmol), 5,5-dimedone (25mmol), p-hydrochloride (25mmol), ionic liquid (0.125mmol), dehydrated alcohol 10mL, join successively in this reaction vessel, reaction vessel is placed in microwave reactor, and in 80 ℃ of lower microwave reactions 20 minutes (ultrasonic power input 400W), after reaction finishes, ethanol is removed in distillation, remaining solid 20mL water washing, filter, filter cake obtains product with ethyl alcohol recrystallization, yield 85%.
Characterization data:
1H NMR (400MHz, DMSO-d
6): δ=7.44 – 7.35 (m, 3H), 7.35 (d, J=3.0Hz, 1H), 7.17 (d, J=8.0Hz, 2H), 6.90 (d, J=4.0Hz, 1H), 2.85 (s, 2H), 2.41 (s, 2H), 2.23 (s, 3H), 1.20 (s, 6H, C (CH
3)
2);
13C NMR (100MHz, CDCl
3): δ 19.75,28.44, and 34.87,37.13,53.70,123.49,126.01,126.25,128.71,130.97,131.68,134.69,135.70,136.48,137.68,156.73,193.55.
Embodiment 11: the recycling of ionic liquid
Take embodiment 1 as example, after reaction finishes, reacting liquid filtering, filter residue filters with the 20mL water washing, and solid obtains product with ethyl alcohol recrystallization, and the filtrate distillation that contains ionic liquid dewaters and directly as the catalyst recirculation of lower secondary response, uses afterwards, react according to embodiment 1 step, during reaction system circulation 4 times, reaction yield is still more than 80%, the acquired results following table:
| Cycle index | Product yield (%) |
| 1 | 83 |
| 2 | 82 |
| 3 | 82 |
| 4 | 81 |
Claims (5)
1. the synthetic method of a tetrahydro-pyrazole ketone derivatives, the structural formula of described tetrahydro-pyrazole ketone derivatives is as shown in the formula in reaction equation 1 (4a), described synthetic method is with the aromatic aldehyde as shown in the structural formula as in reaction equation 1 (1a), shown in formula (2a) 5, aryl hydrazine hydrochloride shown in 5-dimedone and formula (3a) is substrate, take the ionic liquid shown in formula (b) as catalyzer, take ethanol as reaction solvent, under promoting, microwave reacts, after reaction finishes, steam solvent, solid washes filtration with water, filtration cakes torrefaction namely obtains described tetrahydro-pyrazole ketone derivatives by ethyl alcohol recrystallization,
Reaction equation is as follows:
R in the said structure formula
1For hydrogen, methyl, chlorine; R
2For hydrogen, chlorine, nitro.
2. the synthetic method of tetrahydro-pyrazole ketone derivatives as claimed in claim 1, it is characterized in that aromatic aldehyde, 5, the amount of substance of 5-dimedone and hydrazinobenzene hydrochloride salt is than being 1:1:1, and described ionic liquid is (0.02～0.08) with aromatic aldehyde amount of substance ratio: 1.
3. the synthetic method of tetrahydro-pyrazole ketone derivatives as claimed in claim 1, is characterized in that the microwave reaction time is 15～25 minutes.
4. the synthetic method of tetrahydro-pyrazole ketone derivatives as claimed in claim 1, is characterized in that the microwave reaction temperature is 70～80 ℃, and microwave input power is 400W.
5. the synthetic method of tetrahydro-pyrazole ketone derivatives as claimed in claim 1, after it is characterized in that reaction finishes, distill away ethanol, obtain solid product and wash with water, but after the distillation of water-soluble ionic liquid dewaters, direct circulation uses.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103819407A (en) * | 2014-02-26 | 2014-05-28 | 安徽工业大学 | Green catalytic synthesis method for N-(phenylimino)indazole-1-thioamides |
| CN108191764A (en) * | 2018-01-12 | 2018-06-22 | 扬州大学 | The synthetic method of 1,3- diaryl -1,5,6,7- tetrahydrochysene indazole derivatives |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103819407A (en) * | 2014-02-26 | 2014-05-28 | 安徽工业大学 | Green catalytic synthesis method for N-(phenylimino)indazole-1-thioamides |
| CN108191764A (en) * | 2018-01-12 | 2018-06-22 | 扬州大学 | The synthetic method of 1,3- diaryl -1,5,6,7- tetrahydrochysene indazole derivatives |
| CN108191764B (en) * | 2018-01-12 | 2021-04-16 | 扬州大学 | Synthesis method of 1, 3-diaryl-1, 5,6, 7-tetrahydroindazole derivative |
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