CN107903275B - The synthetic method of loop coil 4- hydrogen pyrazole compound - Google Patents
The synthetic method of loop coil 4- hydrogen pyrazole compound Download PDFInfo
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- CN107903275B CN107903275B CN201711208169.6A CN201711208169A CN107903275B CN 107903275 B CN107903275 B CN 107903275B CN 201711208169 A CN201711208169 A CN 201711208169A CN 107903275 B CN107903275 B CN 107903275B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Abstract
The present invention provides a kind of synthetic methods of spiral shell 4- hydrogen ring pyrazole compound, using the Tosylhydrazone class compound of alkynyl connection as raw material, the crude product of loop coil 4- hydrogen pyrazole compound is obtained without catalyst single step reaction in organic solvent, crude product organic solvent is washed, the net product of different structure loop coil 4- hydrogen pyrazole compound is obtained, the present invention is easily-synthesized with no catalyst, raw material, reaction yield is high, without column chromatography, safe advantage easy to operate.Loop coil 4- hydrogen pyrazole compound obtained in the present invention is important chemical industry and medicine intermediate, the compound of certain specific structures, also there is good bioactivity, such as ibutamoren (MK-0677), had a wide range of applications as cancer chemopreventive agent in field of medicaments.In addition to this it is also used as good monodentate ligand and metal forms metal complex, and be expected to be applied on asymmetry catalysis.The reaction equation of this method is as follows:
Description
Technical field
The invention belongs to synthesis technical field more particularly to a kind of synthetic methods of loop coil 4- hydrogen pyrazole compound.
Background technique
Spiro-compound is a kind of basic framework for constructing with bioactive compound, there is many in nature
Substance containing such structural unit.In the past few years, the method for being effectively synthesized loop coil 4- hydrogen pyrazole compound mainly has
The Domino-Heck tandem reaction of palladium chtalyst, c h bond activation etc., to generate spiro-compound, the reaction domain of the existence selectivity
Problem and side reaction is more.And the above method is in terms of directly synthesizing biologically active loop coil 4- hydrogen pyrazole compound
It is related to less.On the other hand, although the document and patent report of a large amount of synthesis 1-/3- hydrogen pyrazole compounds existing at present,
Be be effectively synthesized 4- hydrogen pyrazole compound method but only have individual documents refer to very limited example.Therefore, development is a kind of
The method of loop coil 4- hydrogen pyrazole compound is efficiently synthesized at being highly desirable.
Summary of the invention
In order to solve the above technical problems, the object of the present invention is to provide a kind of direct synthesizing spiro 4- hydrogen pyrazole compounds
Method, this method is at low cost, easy to operate, yield is high, substrate applicability is wide, post-processing is simple and without column chromatograph.
To achieve the above object, present invention employs technical solutions below:
The present invention provides a kind of synthetic methods of loop coil 4- hydrogen pyrazole compound, method includes the following steps:
In organic solvent, the Tosylhydrazone class compound and alkali of formula (I) react in organic solvent, obtain the loop coil of formula (II)
4- hydrogen pyrazole compound, wherein reaction temperature is 25-160 DEG C, and reaction equation is as follows:
Wherein, X is O or NR3；
R is alkyl or aromatic radical；
R1For hydrogen, halogen or alkyl；
R2For aromatic radical or heteroaryl；
R3For hydrogen, alkyl or sulfonyl.
Further alkyl is linear or branched alkyl group.
Preferably, alkyl be methyl, it is ethyl, propyl, isopropyl, butyl, isobutyl group, sec-butyl, tert-butyl, amyl, different
Amyl, tertiary amyl, hexyl or heptyl.
Further, aromatic radical is substituted or unsubstituted phenyl, pyridyl group, naphthalene, benzimidazolyl, benzofuran
Base, quinolyl, isoquinolyl, wherein the substituent group of aromatic radical is alkyl, alkoxy or halogen.
Further, heteroaryl is the substituted or unsubstituted aromatic radical at least one of nitrogen, oxygen and sulphur atom.
Preferably, heteroaryl is 5 members, 6 Yuans or the simultaneously aryl of ring.
It further, can be with one or more substituent groups on aryl and heteroaryl.
Preferably, the substituent group is selected from alkyl, alkoxy, amido, nitro, cyano and halogen；When with multi-substituent
When, this multiple substituent group can be identical or different, and adjacent or similar two substituent groups can mutually indepedent or cyclization.
It is highly preferred that abovementioned alkyl is methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, sec-butyl, tert-butyl, penta
Base, isopentyl, tertiary amyl or hexyl.
It is highly preferred that alkoxy is methoxyl group, ethyoxyl, propoxyl group, isopropoxy, butoxy, isobutoxy, tertiary fourth oxygen
Base or sec-butoxy.
Further, in the present invention, halogen is fluorine, chlorine, bromine or iodine.
Further, sulfonyl is methyl sulphonyl, ethylsulfonyl, tosyl or chlorobenzenesulfonyl.
Preferably, alkali be selected from cesium fluoride, cesium carbonate, potassium carbonate, sodium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide,
One or more of sodium methoxide, sodium ethoxide, tert-butyl alcohol lithium, sodium tert-butoxide, potassium tert-butoxide and triethylamine.
Further, organic solvent be methylene chloride, 1,2- dichloroethanes, chloroform, acetonitrile, Isosorbide-5-Nitrae-dioxane,
Methanol, ethyl alcohol, tetrahydrofuran, toluene, halogeno-benzene, dimethyl sulfoxide and 2, one or more of 2- dimethylbutane.
Preferably, organic solvent is 5-20mL/mmol relative to the Tosylhydrazone class compound amount that alkynyl connects.
Preferably, preferred 85-160 DEG C of reaction temperature.
Further, in the present invention, the reaction time is 8-14 hours.
By above-mentioned technical proposal, compared with prior art, the invention has the following advantages that
The present invention provides a kind of synthetic method of loop coil 4- hydrogen pyrazole compound, wherein Tosylhydrazone class chemical combination
Object and alkali react to obtain loop coil 4- hydrogen pyrazole compound in organic solvent.In the present invention, dipole and alkynes are designed
To intramolecular, can directly react in the case where no catalyst participates in, thus, there is this method raw material easily to prepare, grasp
Make it is simple and safe, chromatographed without catalyst, without column and can to obtain to green high-efficient loop coil 4- hydrogen pyrazole compound etc. excellent
Gesture.
In addition, in the present invention, different linking group (X=linker) can be obtained efficiently as starting material
Target product generates the loop coil 4- hydrogen pyrazole compound of structure diversification.
The above description is only an overview of the technical scheme of the present invention, in order to better understand the technical means of the present invention,
And can be implemented in accordance with the contents of the specification, with presently preferred embodiments of the present invention, detailed description is as follows below.
Brief Description Of Drawings
Fig. 1 is the H spectrogram of 1 product 2a of embodiment in the present invention；
Fig. 2 is the C spectrogram of 1 product 2a of embodiment in the present invention；
Fig. 3 is the H spectrogram of 2 product 2b of embodiment in the present invention；
Fig. 4 is the C spectrogram of 2 product 2b of embodiment in the present invention；
Fig. 5 is the H spectrogram of 3 product 2c of embodiment in the present invention；
Fig. 6 is the C spectrogram of 3 product 2c of embodiment in the present invention；
Fig. 7 is the H spectrogram of 4 product 2d of embodiment in the present invention；
Fig. 8 is the C spectrogram of 4 product 2d of embodiment in the present invention；
Fig. 9 is the H spectrogram of 5 product 2e of embodiment in the present invention；
Figure 10 is the C spectrogram of 5 product 2e of embodiment in the present invention；
Figure 11 is the H spectrogram of 6 product 2f of embodiment in the present invention；
Figure 12 is the C spectrogram of 6 product 2f of embodiment in the present invention；
Figure 13 is the H spectrogram of 7 product 2g of embodiment in the present invention；
Figure 14 is the C spectrogram of 7 product 2g of embodiment in the present invention；
Figure 15 is the H spectrogram of 8 product 2h of embodiment in the present invention；
Figure 16 is the C spectrogram of 8 product 2h of embodiment in the present invention.
Specific embodiment
With reference to embodiment, the embodiment of the present invention is furthur described in detail.Following embodiment is only used
In illustrating the purpose of the present invention, but it is not intended to limit the scope of the invention.
Embodiment 1
Reaction equation is as follows:
By raw material 1a (0.3mmol), potassium carbonate (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room temperature
Under the conditions of be added 2.0mL dioxane dissolution.It is warming up to 90 DEG C to stir 10 hours, solvent is removed under reduced pressure, obtains crude product.It will be thick
Product is washed three times with ethyl acetate (10.0mL X 3), and organic phase is dry, and solvent is removed under reduced pressure, washs 3 with n-hexane
It is secondary to obtain pure loop coil 4- hydrogen pyrazole compound 2a, white solid, purity > 95%, yield 90%.
Nuclear magnetic resonance characterization is done to products therefrom 2a, H spectrum as shown in Figure 1 and C shown in Fig. 2 spectrum, deuterated reagent are
CDCl3。
Embodiment 2
Reaction equation is as follows:
By raw material 1b (0.3mmol), cesium carbonate (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room temperature
Under the conditions of be added 2.0mL dioxane dissolution.It is warming up to 85 DEG C to stir 10 hours, solvent is removed under reduced pressure, obtains crude product.It will be thick
Product is washed three times with ethyl acetate (10.0mL X 3), and organic phase is dry, and solvent is removed under reduced pressure, washs 3 with n-hexane
It is secondary to obtain pure loop coil 4- hydrogen pyrazole compound 2b, white solid, purity > 95%, yield 84%.
Nuclear magnetic resonance characterization is done to products therefrom 2b, H spectrum as shown in Figure 3 and C shown in Fig. 4 spectrum, deuterated reagent are
CDCl3。
Embodiment 3
Reaction equation is as follows:
By raw material 1c (0.3mmol), potassium carbonate (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room temperature
Under the conditions of be added 2.0mL toluene dissolution.It is warming up to 100 DEG C to stir 10 hours, solvent is removed under reduced pressure, obtains crude product.It will slightly produce
Object is washed three times with ethyl acetate (10.0mL X 3), and organic phase is dry, and solvent is removed under reduced pressure, is washed 3 times with n-hexane
Obtain pure loop coil 4- hydrogen pyrazole compound 2c, white solid, purity > 95%, yield 85%.
Nuclear magnetic resonance characterization is done to products therefrom 2c, H spectrum as shown in Figure 5 and C shown in fig. 6 spectrum, deuterated reagent are
CDCl3。
Embodiment 4
Reaction equation is as follows:
By raw material 1d (0.3mmol), sodium methoxide (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room temperature
Under the conditions of be added 2.0mL dioxane dissolution.25 DEG C of room temperature are stirred 12 hours, and solvent is removed under reduced pressure, obtains crude product.It will slightly produce
Object is washed three times with ethyl acetate (10.0mL X 3), and organic phase is dry, and solvent is removed under reduced pressure, is washed 3 times with n-hexane
Obtain pure loop coil 4- hydrogen pyrazole compound 2d, white solid, purity > 95%, yield 83%.
Nuclear magnetic resonance characterization is done to products therefrom 2d, H spectrum as shown in Figure 7 and C shown in Fig. 8 spectrum, deuterated reagent are
CDCl3。
Embodiment 5
Reaction equation is as follows:
By raw material 1e (0.3mmol), potassium hydroxide (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room
The dissolution of 2.0mL dimethyl sulfoxide is added under the conditions of temperature.It is warming up to 160 DEG C to stir 11 hours, solvent is removed under reduced pressure, obtains crude product.
Crude product is washed three times with ethyl acetate (10.0mL X 3), organic phase is dry, and solvent is removed under reduced pressure, is washed with n-hexane
It washs 3 times and obtains pure loop coil 4- hydrogen pyrazole compound 2e, white solid, purity > 95%, yield 87%.
Nuclear magnetic resonance characterization is done to products therefrom 2e, H spectrum as shown in Figure 9 and C shown in Fig. 10 spectrum, deuterated reagent are
CDCl3。
Embodiment 6
Reaction equation is as follows:
By raw material 1f (0.3mmol), potassium carbonate (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room temperature
Under the conditions of be added 2.0mL acetonitrile dissolution.It is warming up to 95 DEG C to stir 10 hours, solvent is removed under reduced pressure, obtains crude product.By crude product
It is washed three times with ethyl acetate (10.0mL X 3), organic phase is dry, and solvent is removed under reduced pressure, and is washed 3 times with n-hexane
To pure loop coil 4- hydrogen pyrazole compound 2f, white solid, purity > 95%, yield 82%.
Nuclear magnetic resonance characterization is done to products therefrom 2f, H spectrum as shown in figure 11 and the spectrum of C shown in Figure 12, deuterated reagent are
CDCl3。
Embodiment 7
Reaction equation is as follows:
By raw material 1g (0.3mmol), potassium carbonate (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room temperature
Under the conditions of be added 2.0mL toluene dissolution.It is warming up to 110 DEG C to stir 14 hours, solvent is removed under reduced pressure, obtains crude product.It will slightly produce
Object is washed three times with ethyl acetate (10.0mL X 3), and organic phase is dry, and solvent is removed under reduced pressure, is washed 3 times with n-hexane
Obtain pure loop coil 4- hydrogen pyrazole compound 2g, purity > 95%, yield 93%.
Nuclear magnetic resonance characterization is done to products therefrom 2g, H spectrum and the spectrum of C shown in Figure 14, deuterated reagent are as shown in fig. 13 that
CDCl3。
Embodiment 8
Reaction equation is as follows:
By raw material 1h (0.3mmol), tert-butyl alcohol lithium (0.6mmol) andMolecular sieve (50mg) is added in reaction flask, room
The dissolution of 2.0mL acetonitrile is added under the conditions of temperature.It is warming up to 80 DEG C to stir 12 hours, solvent is removed under reduced pressure, obtains crude product.It will slightly produce
Object is washed three times with ethyl acetate (10.0mL X 3), and organic phase is dry, and solvent is removed under reduced pressure, is washed 3 times with n-hexane
Obtain pure loop coil 4- hydrogen pyrazole compound 2h, purity > 95%, yield 81%.
Nuclear magnetic resonance characterization is done to products therefrom 2g, H spectrum as shown in figure 15 and the spectrum of C shown in Figure 16, deuterated reagent are
CDCl3。
In conclusion the present invention links dipole from alkynes by different linking groups (X=linker), they are designed
It to an intramolecular, can directly react in the case where no catalyst participates in, obtain the diversified loop coil of functional group
4- hydrogen pyrazole compound.Such compound is important chemical industry and medicine intermediate, and the compound of certain specific structures also has
There is good bioactivity, is had a wide range of applications in field of medicine and chemical technology.This method learning aid has raw material easily to prepare, operate simultaneously
It is simple and safe, without catalyst, without column chromatography, yield it is very high, stablize organic ligand the advantages that.
The above is only a preferred embodiment of the present invention, it is not intended to restrict the invention, it is noted that for this skill
For the those of ordinary skill in art field, without departing from the technical principles of the invention, can also make it is several improvement and
Modification, these improvements and modifications also should be regarded as protection scope of the present invention.
Claims (9)
1. a kind of synthetic method of loop coil 4- hydrogen pyrazole compound, which comprises the following steps: formula (I) to first
Benzene sulfonyl hydrazone compounds and alkali react in organic solvent, obtain the loop coil 4- hydrogen pyrazole compound of formula (II),
Middle reaction temperature is 25-160 DEG C, and reaction equation is as follows:
Wherein, X is O or NR3；
R is alkyl or aromatic radical；
R1For hydrogen, halogen or alkyl；
R2For aromatic radical；
R3For hydrogen, alkyl or sulfonyl.
2. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: the alkyl is
Linear or branched alkyl group.
3. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: R2For heteroaryl,
Contain at least one of nitrogen, oxygen and sulphur atom in the heteroaryl.
4. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: the aromatic radical
For phenyl, pyridyl group, naphthalene, benzimidazolyl, benzofuranyl, quinolyl or isoquinolyl.
5. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: the halogen is
Fluorine, chlorine, bromine or iodine.
6. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: the sulfonyl
For methyl sulphonyl, ethylsulfonyl, tosyl or chlorobenzenesulfonyl.
7. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: the alkali is selected from
Cesium fluoride, cesium carbonate, potassium carbonate, sodium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, the tert-butyl alcohol
One or more of lithium, sodium tert-butoxide, potassium tert-butoxide and triethylamine.
8. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1, it is characterised in that: described organic molten
Agent is selected from methylene chloride, 1,2- dichloroethanes, chloroform, acetonitrile, 1,4- dioxane, methanol, ethyl alcohol, tetrahydrofuran, first
One or more of benzene, halogeno-benzene, dimethyl sulfoxide and 2,2- dimethylbutane.
9. the synthetic method of loop coil 4- hydrogen pyrazole compound according to claim 1 or 8, the organic solvent relative to
Tosylhydrazone class compound amount is 5-20mL/mmol.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418600A (en) * | 2015-11-19 | 2016-03-23 | 苏州大学 | Method for synthesizing polysubstituted 4-carbonyl quinine compound |
| CN106187897A (en) * | 2016-07-14 | 2016-12-07 | 苏州大学 | Synthesis method of fused ring pyrazole compound |
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- 2017-11-27 CN CN201711208169.6A patent/CN107903275B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418600A (en) * | 2015-11-19 | 2016-03-23 | 苏州大学 | Method for synthesizing polysubstituted 4-carbonyl quinine compound |
| CN106187897A (en) * | 2016-07-14 | 2016-12-07 | 苏州大学 | Synthesis method of fused ring pyrazole compound |
Non-Patent Citations (2)
| Title |
|---|
| Copper- or Thermally Induced Divergent Outcomes: Synthesis of 4-Methyl 2H-Chromenes and Spiro-4H-Pyrazoles;Yang Zheng et al.;《Chem. Eur. J.》;20171130;第6705-6711页 |
| Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds;Zhang, Cheng et al.;《Organic & Biomolecular Chemistry》;20171206;第16卷(第5期);第688-692页 |
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