CN105753673A - Improved synthesizing method of 1,5-diketone compound - Google Patents

Improved synthesizing method of 1,5-diketone compound Download PDF

Info

Publication number
CN105753673A
CN105753673A CN201610085846.9A CN201610085846A CN105753673A CN 105753673 A CN105753673 A CN 105753673A CN 201610085846 A CN201610085846 A CN 201610085846A CN 105753673 A CN105753673 A CN 105753673A
Authority
CN
China
Prior art keywords
compound
formula
synthetic method
catalyst
alkali
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201610085846.9A
Other languages
Chinese (zh)
Inventor
辛旭峰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to CN201610085846.9A priority Critical patent/CN105753673A/en
Publication of CN105753673A publication Critical patent/CN105753673A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to an improved synthesizing method of 1,5-diketone compound shown in a formula (III). The improved synthesizing method comprises the following steps of under the nitrogen atmosphere, by utilizing a catalyst, an additive, alkali and an activating agent, adding a compound in a formula (I) and a compound in a formula (II) into an organic solvent to react; after acting, performing post-treatment, so as to obtain the compound in the formula (III), wherein the formula (III) is shown in the attached figure; X is halogen. The improved synthesizing method has the advantage that by adopting a composite reaction system which consists of a particular reaction substrate, the catalyst, the alkali, the activating agent and the organic solvent, the reaction between materials is effectively promoted under the comprehensive action of the system, the conversion of materials into products is promoted, the target product can be obtained at high yield, and the market prospect is broad.

Description

A kind of improvement synthetic method of 1,5-cyclohexadione compounds
Technical field
The present invention relates to the synthetic method of a kind of carbonyls, relate more particularly to a kind of 1,5- The improvement synthetic method of cyclohexadione compounds, belongs to organic chemical synthesis field.
Background technology
Cyclohexadione compounds is the compound that a class is important, its important frequently as in organic synthesis Synthesis unit is to build other medicines compound or functional material.Therefore, research diones chemical combination The synthetic method of thing is also a thing the most significant, and it is to chemical industry, medicine synthesis field The most necessary.
The synthetic method of cyclohexadione compounds often relates to the Michael of alpha, beta-unsaturated carbonyl compound Addition reaction, and deepening continuously recently as research, occur in that the most successively many other Synthetic method, such as:
(" the One-pot Synthesis of 1,5-diketones catalyzed such as Akira Yanagisawa By barium isopropoxide ", Tetrahedron, 2007,63,8581-8585) report one The benzaldehyde using titanate catalyst catalysis reacts preparation 1,5-diketone chemical combination with acetophenone compounds The method of thing, its reaction equation is as follows:
Andreas Marx etc. (" Aluminum Bis (trifluoromethylsulfonyl) amides: New Highly Efficient and Remarkably Versatile Catalysts for C-C Bond Formation Reactions ", Angew.Chem.Int.Ed., 2000,39,178-181) report A kind of alpha, beta-unsaturated carbonyl compound prepares dione compounds with silylenolethers compounds reaction Method, its reaction equation is as follows:
As it has been described above, prior art discloses the multiple method of synthesis cyclohexadione compounds, but These methods still suffer from certain defect, such as substrate still need to be expanded, reaction yield too low etc..
Therefore, for developing the novel method for synthesizing of cyclohexadione compounds, still suffer from continuing research Necessity, this power place that present invention is accomplished the most just and basis leaned on.
Summary of the invention
In order to overcome many defects as indicated above and seek the novel of cyclohexadione compounds Synthetic method, present inventor has performed in-depth study and exploration, is paying enough creation Property work after, thus complete the present invention.
It should be noted that the present invention is to make on the basis of the another piece patent application applied on the same day The improvement gone out, the content of another piece application can be incorporated by reference into into using as reference, at this No longer it is described in detail.
Specifically, technical scheme and content relate under one shown in formula (III) 1,5- The improvement synthetic method of cyclohexadione compounds, described method includes: under nitrogen atmosphere, in urging In the presence of agent, auxiliary agent, alkali and activator, in organic solvent add under (I) compound and under Formula (II) compound reacts, and reacts through post processing after terminating, thus obtains described formula (III) and change Compound,
Wherein, X is halogen.
In the described synthetic method of the present invention, described halogen is halogen, can be such as F, Cl, Br or I.
In the described synthetic method of the present invention, described catalyst is [1,1 '-bis-(diphenylphosphines) two Cyclopentadienyl iron] Nickel Chloride, TFMS nickel, double (diphenylphosphine propane) Nickel Chloride of 1,3- ((DPPP)NiCl2) or double (diphenylphosphine) ethane chlorination nickel ((DPPE) NiCl of 1,2-2Any in) One, double (diphenylphosphine propane) Nickel Chloride ((DPPP) NiCl of most preferably 1,3-2)。
In the described synthetic method of the present invention, described auxiliary agent is zirconium acetate.
In the described synthetic method of the present invention, described alkali is NaOH, sodium carbonate, cesium carbonate, Sodium phosphate, potassium acetate, potassium tert-butoxide, caustic alcohol, 1,4-diazabicylo [2.2.2] octane (DABCO) any one or in diethanol amine, most preferably cesium carbonate.
In the described synthetic method of the present invention, described activator is 2-fluorobenzoic boric acid pinacol In ester, 2-bromomethyl-4-fluorobenzoic boric acid pinacol ester or 4-amino-2-fluorobenzoic boric acid pinacol ester Any one, most preferably 4-amino-2-fluorobenzoic boric acid pinacol ester.
In the described synthetic method of the present invention, described organic solvent is DMF (N, N-dimethyl Formamide), DMSO (dimethyl sulfoxide (DMSO)), benzene, acetonitrile, 1-METHYLPYRROLIDONE (NMP) or Any one or the most multiple mixture, most preferably volume ratio 1:3 in Isosorbide-5-Nitrae-dioxane The mixture of DMF (N,N-dimethylformamide) and acetonitrile.
Wherein, the consumption of described organic solvent does not has strict restriction, those skilled in the art Can suitably select according to actual conditions and determine, such as its consumption size is to facilitate reaction Carry out and post-process, being no longer described in detail at this.
In the described synthetic method of the present invention, described formula (I) compound rubs with formula (II) compound That ratio is 1:1.5-2.5, such as, can be 1:1.5,1:2 or 1:2.5.
In the described synthetic method of the present invention, described formula (I) compound and the mol ratio of catalyst For 1:0.1-0.16, such as, can be 1:0.1,1:0.13 or 1:0.16.
In the described synthetic method of the present invention, described formula (I) compound with the mol ratio of auxiliary agent is 1:0.05-0.1, such as, can be 1:0.5,1:0.07,1:0.09 or 1:0.1.
In the described synthetic method of the present invention, described formula (I) compound with the mol ratio of alkali is 1:2-3, such as, can be 1:2,1:2.5 or 1:3.
In the described synthetic method of the present invention, described formula (I) compound and the mol ratio of activator For 1:0.08-0.14, such as, can be 1:0.08,1:0.1,1:0.12 or 1:0.14.
In the described synthetic method of the present invention, reaction temperature is 80-100 DEG C, such as, can be 80 DEG C, 90 DEG C or 100 DEG C.
In the described synthetic method of the present invention, the reaction time is 6-9 hour, such as, can be 6 Hour, 7 hours, 8 hours or 9 hours.
In the described synthetic method of the present invention, the post processing after reaction terminates can be specific as follows: After reaction terminates, reacting liquor while hot being filtered, the pH value of regulation filtrate, to neutral, is then used Saturated aqueous common salt fully washs, and adds ether and extracts 2-3 time, merges organic phase, anhydrous Magnesium sulfate is dried, reduced pressure concentration, and gained residue crosses 300-400 mesh silica gel column chromatography, with The acetone of equal-volume ratio and the mixed liquor of petroleum ether carry out drip washing, thus obtain described formula (III) Compound.
In sum, the invention provides a kind of 1, the improvement synthesis side of 5-cyclohexadione compounds Method, the method uses by unique reaction substrate, catalyst, auxiliary agent, alkali, activator and has The recombination reaction system of machine solvent composition, thus effectively promoted by the comprehensive function of this kind of system Enter the reaction of storeroom, promoted the material conversion to product, mesh can have been obtained with high yield Product, there are market prospects widely.
Detailed description of the invention
Below by specific embodiment, the present invention is described in detail, but these are exemplary The purposes of embodiment and purpose are only used for enumerating the present invention, the not actual guarantor to the present invention Scope of protecting constitutes any type of any restriction, more non-protection scope of the present invention is confined to This.
Embodiment 1
Under room temperature and nitrogen atmosphere, the appropriate organic solvent in reactor is (for volume ratio 1:3 The mixture of DMF (DMF) and acetonitrile) in, add 100mmol above formula (I) compound, 200mmol upper formula (II) compound, the double (diphenyl of 15mmol catalyst 1,3- Phosphine propane) Nickel Chloride ((DPPP) NiCl2), 8mmol auxiliary agent zirconium acetate, 300mmol alkali Cesium carbonate and 11mmol activator 4-amino-2-fluorobenzoic boric acid pinacol ester, then heat to 85 DEG C, and be sufficiently stirred at such a temperature reacting 8 hours；
After reaction terminates, reacting liquor while hot being filtered, the pH value of regulation filtrate is to neutral, so Fully wash with saturated aqueous common salt afterwards, add ether and extract 2-3 time, merge organic phase, nothing Water magnesium sulfate is dried, reduced pressure concentration, and gained residue crosses 300-400 mesh silica gel column chromatography, with The acetone of equal-volume ratio and the mixed liquor of petroleum ether carry out drip washing, thus obtain upper formula (III) chemical combination Thing, productivity is 93.8%.
1H NMR(CDCl3, 400MHz): δ 7.98 (d, J=7.2Hz, 4H)；7.52-7.55 (m,2H)；7.42-7.46(m,4H)；7.15-7.31(m,2H)；6.82-6.88(m,2H)； 4.33-4.35(m,1H)；3.76(s,3H)；3.41-3.52(m,4H).
Embodiment 2
Reaction equation is with embodiment 1, and specific operation process is as follows:
Under room temperature and nitrogen atmosphere, the appropriate organic solvent in reactor is (for volume ratio 1:3 The mixture of DMF (DMF) and acetonitrile) in, add 100mmol above formula (I) compound, 150mmol upper formula (II) compound, the double (diphenyl of 10mmol catalyst 1,3- Phosphine propane) Nickel Chloride ((DPPP) NiCl2), 5mmol auxiliary agent zirconium acetate, 200mmol alkali Cesium carbonate and 8mmol activator 4-amino-2-fluorobenzoic boric acid pinacol ester, then heat to 80 DEG C, and be sufficiently stirred at such a temperature reacting 9 hours；
After reaction terminates, reacting liquor while hot being filtered, the pH value of regulation filtrate is to neutral, so Fully wash with saturated aqueous common salt afterwards, add ether and extract 2-3 time, merge organic phase, Anhydrous magnesium sulfate is dried, reduced pressure concentration, and gained residue crosses 300-400 mesh silica gel column chromatography, Carry out drip washing with the acetone of equal-volume ratio and the mixed liquor of petroleum ether, thus obtain upper formula (III) Compound, productivity is 93.6%.
Nuclear magnetic data is with embodiment 1.
Embodiment 3
Reaction equation is with embodiment 1, and specific operation process is as follows:
Under room temperature and nitrogen atmosphere, the appropriate organic solvent in reactor is (for volume ratio 1:3 The mixture of DMF (DMF) and acetonitrile) in, add 100mmol above formula (I) compound, 220mmol upper formula (II) compound, the double (diphenyl of 12mmol catalyst 1,3- Phosphine propane) Nickel Chloride ((DPPP) NiCl2), 10mmol auxiliary agent zirconium acetate, 250mmol alkali Cesium carbonate and 14mmol activator 4-amino-2-fluorobenzoic boric acid pinacol ester, then heat to 90 DEG C, and be sufficiently stirred at such a temperature reacting 7 hours；
After reaction terminates, reacting liquor while hot being filtered, the pH value of regulation filtrate is to neutral, so Fully wash with saturated aqueous common salt afterwards, add ether and extract 2-3 time, merge organic phase, Anhydrous magnesium sulfate is dried, reduced pressure concentration, and gained residue crosses 300-400 mesh silica gel column chromatography, Carry out drip washing with the acetone of equal-volume ratio and the mixed liquor of petroleum ether, thus obtain upper formula (III) Compound, productivity is 93.9%.
Nuclear magnetic data is with embodiment 1.
Embodiment 4
Reaction equation is with embodiment 1, and specific operation process is as follows:
Under room temperature and nitrogen atmosphere, the appropriate organic solvent in reactor is (for volume ratio 1:3 The mixture of DMF (DMF) and acetonitrile) in, add 100mmol above formula (I) compound, 250mmol upper formula (II) compound, the double (diphenyl of 16mmol catalyst 1,3- Phosphine propane) Nickel Chloride ((DPPP) NiCl2), 7mmol auxiliary agent zirconium acetate, 280mmol alkali Cesium carbonate and 12mmol activator 4-amino-2-fluorobenzoic boric acid pinacol ester, then heat to 100 DEG C, and be sufficiently stirred at such a temperature reacting 6 hours；
After reaction terminates, reacting liquor while hot being filtered, the pH value of regulation filtrate is to neutral, so Fully wash with saturated aqueous common salt afterwards, add ether and extract 2-3 time, merge organic phase, Anhydrous magnesium sulfate is dried, reduced pressure concentration, and gained residue crosses 300-400 mesh silica gel column chromatography, Carry out drip washing with the acetone of equal-volume ratio and the mixed liquor of petroleum ether, thus obtain upper formula (III) Compound, productivity is 94.1%.
Nuclear magnetic data is with embodiment 1.
Embodiment 5-16
Embodiment 5-8: except by catalyst (DPPP) NiCl2Replace with [1,1 '-bis-(diphenylphosphines) Ferrocene] outside Nickel Chloride, other operation is the most constant, thus repeats to implement embodiment 1-4, Sequentially obtain embodiment 5-8.
Embodiment 9-12: except by catalyst (DPPP) NiCl2Replace with outside TFMS nickel, Other operation is the most constant, and other operation is the most constant, thus repeats to implement embodiment 1-4, suitable Secondary obtain embodiment 9-12.
Embodiment 13-16: except by catalyst (DPPP) NiCl2Replace with 1,2-double (diphenylphosphine) Ethane chlorination nickel ((DPPE) NiCl2) outward, other operation is the most constant, thus repeats to implement enforcement Example 1-4, sequentially obtains embodiment 13-16.
Result see table 1.
Table 1
As can be seen here, in all of catalyst, 1,3-double (diphenylphosphine propane) Nickel Chlorides ((DPPP)NiCl2) there is best catalytic effect, even if similar with it 1,2-double (two Phenylphosphine) ethane chlorination nickel ((DPPE) NiCl2) (differ only by-a CH2-), productivity also has Significantly reducing, other catalyst then reduces the most notable.
Embodiment 17-20
In addition to being omitted by auxiliary agent zirconium acetate, other operation is the most constant, thus repeats to implement Embodiment 1-4, sequentially obtains embodiment 17-20.It was found that the product of embodiment 17-20 Productivity is 87.7-88.5%, has significantly reduction compared with embodiment 1-4.This proves acetic acid The existence of zirconium, it is possible to significantly improve reaction effect, improves products collection efficiency.
Embodiment 21-52
Embodiment 21-24: be in addition to NaOH except alkali cesium carbonate being replaced with consumption, other operation The most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 21-24.
Embodiment 25-28: be in addition to sodium carbonate except alkali cesium carbonate being replaced with consumption, other operation The most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 25-28.
Embodiment 29-32: be in addition to sodium phosphate except alkali cesium carbonate being replaced with consumption, other operation The most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 29-32.
Embodiment 33-36: be in addition to potassium acetate except alkali cesium carbonate being replaced with consumption, other operation The most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 33-36.
Embodiment 37-40: be in addition to potassium tert-butoxide except alkali cesium carbonate being replaced with consumption, other behaviour Make the most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 37-40.
Embodiment 41-44: be in addition to caustic alcohol except alkali cesium carbonate being replaced with consumption, other operation The most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 41-44.
Embodiment 45-48: be in addition to DABCO except alkali cesium carbonate being replaced with consumption, other behaviour Make the most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 45-48.
Embodiment 49-52: be in addition to diethanol amine except alkali cesium carbonate being replaced with consumption, other behaviour Make the most constant, thus repeat to implement embodiment 1-4, sequentially obtain embodiment 49-52.
Result see table 2.
Table 2
As can be seen here, in all of alkali, cesium carbonate has best effects, even if non-with it Similar sodium carbonate, its productivity also has significantly reduction.
Embodiment 53-64
Embodiment 53-56: except activator 4-amino-2-fluorobenzoic boric acid pinacol ester is replaced with 2- Outside fluorobenzoic boric acid pinacol ester, other operation is the most constant, thus repeats to implement embodiment 1-4, Sequentially obtain embodiment 53-56.
Embodiment 57-60: except activator 4-amino-2-fluorobenzoic boric acid pinacol ester is replaced with 2- Outside bromomethyl-4-fluorobenzoic boric acid pinacol ester, other operation is the most constant, thus repeats to implement reality Execute example 1-4, sequentially obtain embodiment 57-60.
Embodiment 61-64: except activator 4-amino-2-fluorobenzoic boric acid pinacol ester is omitted Outward, other operation is the most constant, thus repeats to implement embodiment 1-4, sequentially obtains embodiment 61-64。
Result see table 3.
Table 3
Note: the products collection efficiency of the embodiment 64 corresponding to embodiment 1 in " * " is 57.3%.
As can be seen here, in all of activator, 4-amino-2-fluorobenzoic boric acid pinacol ester has Best activation effect, even if the 2-fluorobenzoic boric acid pinacol ester similar with it, it produces Rate also has the reduction of up to 4-5 percentage point.
Embodiment 65-70
In addition to using following single solvent, other operation is the most constant, thus repeats to implement reality Execute example 1-3, obtain embodiment 65-60.Used solvent combination, embodiment corresponding relation and Products collection efficiency see table 4,
Table 4
As can be seen here, when using any single solvent, productivity all has significantly reduction. But it was unexpectedly determined that when the mixture of volume ratio 1:3 both using, but can obtain height Reach the excellent productivity (see embodiment 1-4) of about 94%, thus demonstrate both uses mixture Beyond thought technique effect can be obtained.
Embodiment 71-
In addition to using following solvent combination, other operation is the most constant, thus repeats to implement reality Execute example 1-7.The solvent combination, embodiment corresponding relation and the products collection efficiency that are used see table 5, Wherein organic solvent is defined as component A and the mixture of component B that volume ratio is 1:3.
Table 5
As can be seen here, in all of solvent, only DMF just can take with the mixture of acetonitrile Obtaining best technique effect, the component two-by-two of other solvent all can not obtain the most excellent product Productivity.
In sum, the invention provides a kind of 1, the improvement synthesis side of 5-cyclohexadione compounds Method, the method uses by unique reaction substrate, catalyst, auxiliary agent, alkali, activator and has The recombination reaction system of machine solvent composition, thus effectively promoted by the comprehensive function of this kind of system Enter the reaction of storeroom, promoted the material conversion to product, mesh can have been obtained with high yield Product, there are market prospects widely.
Should be appreciated that the purposes of these embodiments is merely to illustrate the present invention and is not intended to limit this The protection domain of invention.Additionally, it will also be appreciated that after the technology contents having read the present invention, The present invention can be made various change, amendment and/or modification by those skilled in the art, all of this Within a little equivalent form of values fall within the protection domain that the application appended claims is limited equally.

Claims (10)

1. shown in a lower formula (III) 1, the improvement synthetic method of 5-cyclohexadione compounds, described side Method includes: under nitrogen atmosphere, in the presence of catalyst, auxiliary agent, alkali and activator, and Xiang You Under adding in machine solvent, (I) compound and lower formula (II) compound react, reaction terminate after through after Process, thus obtain described formula (III) compound,
Wherein, X is halogen.
2. synthetic method as claimed in claim 1, it is characterised in that: described catalyst is Double (the diphenyl of [1,1 '-bis-(diphenylphosphine) ferrocene] Nickel Chloride, TFMS nickel, 1,3- Phosphine propane) Nickel Chloride ((DPPP) NiCl2) or double (diphenylphosphine) the ethane chlorination nickel of 1,2- ((DPPE)NiCl2Any one in), double (diphenylphosphine propane) dichloride of most preferably 1,3- Nickel ((DPPP) NiCl2)。
3. synthetic method as claimed in claim 1 or 2, it is characterised in that: described auxiliary agent For zirconium acetate.
4. the synthetic method as described in any one of claim 1-3, it is characterised in that: described Alkali is NaOH, sodium carbonate, cesium carbonate, sodium phosphate, potassium acetate, potassium tert-butoxide, ethanol Any one in sodium, Isosorbide-5-Nitrae-diazabicylo [2.2.2] octane (DABCO) or diethanol amine, Most preferably cesium carbonate.
5. the synthetic method as described in any one of claim 1-4, it is characterised in that: described work Agent is 2-fluorobenzoic boric acid pinacol ester, 2-bromomethyl-4-fluorobenzoic boric acid pinacol ester or 4-amino Any one in-2-fluorobenzoic boric acid pinacol ester, most preferably 4-amino-2-fluorobenzoic boric acid frequency Any alcohol ester.
6. the synthetic method as described in any one of claim 1-5, it is characterised in that: described formula (I) compound is 1:1.5-2.5 with the mol ratio of formula (II) compound.
7. the synthetic method as described in any one of claim 1-6, it is characterised in that: described formula (I) compound is 1:0.1-0.16 with the mol ratio of catalyst.
8. the synthetic method as described in any one of claim 1-7, it is characterised in that: described formula (I) compound is 1:0.05-0.1 with the mol ratio of auxiliary agent.
9. the synthetic method as described in any one of claim 1-8, it is characterised in that: described formula (I) compound is 1:2-3 with the mol ratio of alkali.
10. the synthetic method as described in any one of claim 1-9, it is characterised in that: state formula (I) Compound is 1:0.08-0.14 with the mol ratio of activator.
CN201610085846.9A 2016-02-15 2016-02-15 Improved synthesizing method of 1,5-diketone compound Pending CN105753673A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201610085846.9A CN105753673A (en) 2016-02-15 2016-02-15 Improved synthesizing method of 1,5-diketone compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201610085846.9A CN105753673A (en) 2016-02-15 2016-02-15 Improved synthesizing method of 1,5-diketone compound

Publications (1)

Publication Number Publication Date
CN105753673A true CN105753673A (en) 2016-07-13

Family

ID=56329791

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610085846.9A Pending CN105753673A (en) 2016-02-15 2016-02-15 Improved synthesizing method of 1,5-diketone compound

Country Status (1)

Country Link
CN (1) CN105753673A (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020065192A1 (en) * 2000-02-18 2002-05-30 Mackenzie Peter Borden Productivity catalysts and microstructure control

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020065192A1 (en) * 2000-02-18 2002-05-30 Mackenzie Peter Borden Productivity catalysts and microstructure control

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
T.V.MOSKOVKINA等: "Transformations of Stereoisomeric 2-Chloro-3-R-pentane-1,5-diones in Reaction with Phenylhydrazine", 《RUSSIAN JOURNAL OF ORGANIC CHEMISTRY》 *
WANG CAN等: "One-pot Synthesis of 3-Aryl-1,5-bis(2-hydroxyaryl)pentane-1,5-diones", 《CHINESE JOURNAL OF CHEMISTRY》 *
ZHENG LI等: "Copper-catalyzed synthesis of 1,3,5- triarylpentane-1,5-diones from a,b-unsaturated ketones", 《RSC ADV》 *

Similar Documents

Publication Publication Date Title
Karmakar et al. A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction
CN109575014B (en) Benzimidazo [2,1-a ] isoquinolinone compound and preparation method thereof
CN105198841A (en) Synthetic method for drug intermediate polysubstituted furan compound
CN105753673A (en) Improved synthesizing method of 1,5-diketone compound
Nair et al. Nickel-catalysed fluoromethylation reactions
CN104961734A (en) Method for synthetizing medical intermediate heterocyclic group pyridine N-oxide
CN104692986A (en) Method for synthesizing medical intermediate phenanthrene compound
CN104447391A (en) Methylenebisamide derivative and preparation method thereof
CN105330690B (en) A kind of synthetic method of pharmaceutical intermediate aryl ketones phosphonate compound
UA88992C2 (en) Process for the production of carboxanilides
CN104803912B (en) A kind of synthetic method of medicine intermediate quinoline compound
CN107915653A (en) Catalysis ester and amine carry out the method that reaction prepares acid amides
CN105566221A (en) Synthetic method for condensed ring amide compound
CN105481768A (en) Synthetic method for drug intermediate diaryl ketone compound
CN105777510A (en) Synthesizing method for diketone compound
CN105367465A (en) Synthetic method of medical intermediate carbonyl-replacement aryl thioether compound
CN105153045B (en) A kind of synthetic method of pharmaceutical intermediate quinazoline derivant
CN103880675A (en) Improved catalyzed synthesis method for 1,4-dicarbonyl compound
CN105777538B (en) A kind of synthetic method of medicine intermediate benzyl ester type compound
CN111116510B (en) 2-substituted methylene dihydrobenzo [ d ] thiazole derivatives and synthesis method and application thereof
CN105294600B (en) A kind of synthetic method of medicine intermediate diketone aminated compounds
CN104974000A (en) Method for di-trifluoromethylation reaction of styryl compound
CN105237436A (en) Synthetic method for dicyano substituted amine compounds
CN105859620A (en) 6-trichloromethyl phenanthridine compound and preparation method and application thereof
CN105367512A (en) Synthesizing method of medicine intermediate benzothiazole compound

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20160713

RJ01 Rejection of invention patent application after publication