CN103664796A - Synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid - Google Patents
Synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid Download PDFInfo
- Publication number
- CN103664796A CN103664796A CN201310648660.6A CN201310648660A CN103664796A CN 103664796 A CN103664796 A CN 103664796A CN 201310648660 A CN201310648660 A CN 201310648660A CN 103664796 A CN103664796 A CN 103664796A
- Authority
- CN
- China
- Prior art keywords
- pyrimidyl
- carboxyl
- dicarboxylic acid
- benzene dicarboxylic
- acid
- 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
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
Abstract
The invention discloses a synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid, the synthesis method is as follows: first, synthesizing a compound A 5-[2-(4,4,5,5-tetramethyl-1,3,2-boric acid ether)]-1,3-benzoic acid dimethyl ester, then in argon or nitrogen protection conditions, performing a reflux reaction of the compound A and ethyl 2-chloropyrimidine-5-carboxylate in an organic solvent by adding of a catalyst to produce the final target compound B 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid, and compared with the prior art, the synthesis method has the advantages of low synthesis cost, high yield and high product purity.
Description
Technical field
The present invention relates to a kind of synthetic method, particularly a kind of 5-[2-(5-carboxyl-pyrimidyl) of nitrogen heterocyclic ring biphenyl triangle Carboxylic acid ligand compound]-1, the synthetic method of 3-benzene dicarboxylic acid.
Background technology
Triangle carboxylic-acid part has good pore passage structure, large internal surface area, makes their title complexs have potential application at aspects such as the storage of gas, separation, luminescent materials.And nitrogen heterocyclic ring biphenyl triangle Carboxylic acid ligand changes the structure of its compound, thereby and make in its pore electronic environment be optimized to have improved above-mentioned application performance.In addition, the compound of triangle carboxylic-acid part synthesized has potential using value in fields such as optics, catalysis, magnetic, functional materialss, becomes one of focus of current research.Yet large-sized multi-carboxylic acid compounds is synthetic and difficult.Therefore related 5-[2-(5-carboxyl-pyrimidyl) in the present invention]-1,3-benzene dicarboxylic acid is a kind of part with huge potential commercial value.But the synthetic method cost of bibliographical information is expensive at present, and productive rate is lower, has largely limited the research and probe to its using value.
Summary of the invention
The object of this invention is to provide the 5-[2-that a kind of synthetic cost is low, productive rate is high, product purity is high (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, overcomes the deficiencies in the prior art.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, synthesis step is:
(I) is under the condition of argon gas or nitrogen protection, with the different peptide acid of 5-bromine two formicesters, connection boric acid pinacol ester and potassium acetate in molar ratio 1 ︰ 0.8～1.5 ︰ 2.8～3.5 are dissolved in dioxane after mixing, the amount ratio of the different peptide of 5-bromine acid two formicesters and dioxane is 1 rub in the least 2.6～2.8 milliliters of ︰, add appropriate catalyzer, under 110～130 ℃ of oil baths, back flow reaction is 10～35 hours, cooling rear first dilute with water extracts system with methylene dichloride again, then with strong brine, organic layer is washed, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, last take sherwood oil and ethyl acetate and as the mixed solvent of 10 ︰ 0.8～1.2 as eluent, with column chromatography separating-purifying, obtain target compound A:5-[2-(4 by volume, 4, 5, 5-tetramethyl--1, 3, 2-boric acid ether)]-1, 3-phenylformic acid dimethyl ester,
(II), under argon gas or nitrogen protection, the A that upper step is obtained and 2-chloropyrimide-5-carboxylic acid, ethyl ester in molar ratio 1.2 ︰ 1 mix and dissolve in K
2cO
3solution, ethanol and toluene is by volume in the mixed solvent of 1 ︰ 0.8～1.2 ︰ 2.8～3.2, A and K
2cO
3the amount ratio of solution is 0.6～0.9 milliliter of 1 Hao Mo ︰, add proper catalyst, under 90 ~ 110 ℃ of oil baths, react 10 ~ 40 hours, cooling rear first dilute with water extracts system with methylene dichloride again, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, then take methylene dichloride and acetone by volume as 99 ︰ 0.5～1.5 are eluent, with column chromatography separating-purifying, obtain white product, white product is hydrolyzed, being acidified to pH=2 white solid separates out, vacuum-drying obtains final compd B: 5-[2-(5-carboxyl-pyrimidyl)]-1, 3-benzene dicarboxylic acid.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, with the different peptide of 5-bromine acid two formicesters, connection boric acid pinacol ester and potassium acetate 1 ︰ 1 ︰ 3 synthetic compound A in molar ratio.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, the catalyzer of preparing compd A use is [1,1 '-bis-(diphenylphosphine) diamyl iron] palladium chloride, consumption is for participating in 0.2～0.5% of reactant total mass.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, preparing compd B solvent for use is K
2cO
3solution, ethanol and toluene is the mixed solvent of 1 ︰ 1 ︰ 3 by volume, K
2cO
3the concentration of solution is 2 M.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, while preparing compd B, used catalyst is tetra-triphenylphosphine palladium, consumption is for participating in 0.2～0.5% of reactant total mass.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, the eluent of using while preparing the separation of compd A column chromatography is that sherwood oil and ethyl acetate volume ratio are the mixed solvent of 10 ︰ 1.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, the eluent of using while preparing the separation of compd B column chromatography is that methylene dichloride and acetone volume ratio are the mixed solvent of 99 ︰ 1.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid compared with prior art has advantages of that synthetic cost is low, productive rate is high, product purity is high.
Accompanying drawing explanation
Compound in Fig. 1 the present invention
a'schemical formula schematic diagram;
Compound in Fig. 2 the present invention
asynthetic route schematic diagram;
Compound in Fig. 3 the present invention
bsynthetic route schematic diagram;
Compound in Fig. 4 the present invention
ainfrared spectrum;
Compound in Fig. 5 the present invention
binfrared spectrum.
Embodiment
First synthetic compound
a: 5-[2-(4,4,5; 5-tetramethyl--1,3,2-boric acid ether)]-1; 3-phenylformic acid dimethyl ester then adds catalyzer by itself and 2-chloropyrimide-5-carboxylic acid, ethyl ester back flow reaction in organic solvent under argon gas or nitrogen protection condition, generates ultimate aim compound
b: 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, synthesis step is:
(I) is under the condition of argon gas or nitrogen protection, with the different peptide acid of 5-bromine two formicesters, connection boric acid pinacol ester and potassium acetate in molar ratio 1 ︰ 0.8～1.5 ︰ 2.8～3.5 are dissolved in dioxane after mixing, the amount ratio of the different peptide of 5-bromine acid two formicesters and dioxane is 1 rub in the least 2.6～2.8 milliliters of ︰, add appropriate catalyzer, under 110～130 ℃ of oil baths, back flow reaction is 10～35 hours, cooling rear first dilute with water extracts system with methylene dichloride again, then with strong brine, organic layer is washed, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, last take sherwood oil and ethyl acetate and as the mixed solvent of 10 ︰ 0.8～1.2 as eluent, with column chromatography separating-purifying, obtain target compound A:5-[2-(4 by volume, 4, 5, 5-tetramethyl--1, 3, 2-boric acid ether)]-1, 3-phenylformic acid dimethyl ester,
(II), under argon gas or nitrogen protection, the A that upper step is obtained and 2-chloropyrimide-5-carboxylic acid, ethyl ester in molar ratio 1.2 ︰ 1 mix and dissolve in K
2cO
3solution, ethanol and toluene is by volume in the mixed solvent of 1 ︰ 0.8～1.2 ︰ 2.8～3.2, A and K
2cO
3the amount ratio of solution is 0.6～0.9 milliliter of 1 Hao Mo ︰, add proper catalyst, under 90 ~ 110 ℃ of oil baths, react 10 ~ 40 hours, cooling rear first dilute with water extracts system with methylene dichloride again, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, then take methylene dichloride and acetone by volume as 99 ︰ 0.5～1.5 are eluent, with column chromatography separating-purifying, obtain white product, white product is hydrolyzed, being acidified to pH=2 white solid separates out, vacuum-drying obtains final compd B: 5-[2-(5-carboxyl-pyrimidyl)]-1, 3-benzene dicarboxylic acid.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, with the different peptide of 5-bromine acid two formicesters, connection boric acid pinacol ester and potassium acetate 1 ︰ 1 ︰ 3 synthetic compound A in molar ratio.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, the catalyzer of preparing compd A use is [1,1 '-bis-(diphenylphosphine) diamyl iron] palladium chloride, consumption is for participating in 0.2～0.5% of reactant total mass.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, preparing compd B solvent for use is K
2cO
3solution, ethanol and toluene is the mixed solvent of 1 ︰ 1 ︰ 3 by volume, K
2cO
3the concentration of solution is 2 M.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, while preparing compd B, used catalyst is tetra-triphenylphosphine palladium, consumption is for participating in 0.2～0.5% of reactant total mass.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, the eluent of using while preparing the separation of compd A column chromatography is that sherwood oil and ethyl acetate volume ratio are the mixed solvent of 10 ︰ 1.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, the eluent of using while preparing the separation of compd B column chromatography is that methylene dichloride and acetone volume ratio are the mixed solvent of 99 ︰ 1.
Specific embodiment is as follows:
As shown in Figure 1, 2: (I) is under the condition of nitrogen protection; to be dissolved in 20 ml dioxane after the different peptide acid of 5-bromine two formicester 2.0 g (7.32 mmol), connection boric acid pinacol ester 1.85 g (7.32 mmol) and potassium acetate 2.16 g (22 mmol) 1:1:3 mixing in molar ratio; add 160 mg(3%) [1; 1 '-bis-(diphenylphosphine) diamyl iron] palladium chloride catalyzer, under 128 ℃ of oil baths, back flow reaction is 24 hours.The cooling rear 20 ml water dilutions that first add, then divide and add altogether for four times 80 ml methylene dichloride to extract system, then with 80 ml strong brines, organic layer is washed, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, finally take sherwood oil and ethyl acetate as the mixed solvent of 10:1 as eluent, with column chromatography separating-purifying, to obtain compound by volume
a2.09 g, productive rate 89.13%.
Infrared spectrum is shown in Fig. 4, and main peaks ownership is as follows: 2987,2861(C-H); 1730(C=O); 1604,1459 (phenyl ring characteristic peaks); 1250,1140(C-O-C).
As shown in Figure 3: (II) is under nitrogen protection, by compound
a1.00 g(5.36 mmol) with 2-chloropyrimide-5-carboxylic acid, ethyl ester 2.00 g (6.25 mmol) in molar ratio 1.2:1 after mixing, pour in flask, add 4 ml 2 M K
2cO
3the mixed solvent of solution, 4 ml ethanol and 12 ml toluene, adding 0.31 g (0.26 mmol) tetra-triphenylphosphine palladium is catalyzer, under 101 ℃ of oil baths, reacts 24 hours.The cooling rear 20 ml water dilutions that first add, then divide and add for four times 80 ml methylene dichloride to extract system, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, then take methylene dichloride and acetone by volume as 99:1 is eluent, with column chromatography separating-purifying, obtain white product.At room temperature, with 5 ml 5 M KOH solution, 5 ml tetrahydrofuran (THF)s and 5 ml alcohol mixed solvents, white product is hydrolyzed 24 hours, filters, pour 25 ml water dilutions into, with 4 M HCl, be acidified to pH=2, white solid is separated out, filter, vacuum-drying obtains compound
b0.74g, productive rate 47.40%.
1H?NMR?(300?MHz,?DMSO-d6)?δ?9.29?(s,?2H),?9.17?(d,?J?=?1.2?Hz,?2H),?and?8.61?(d,?J?=?1.5?Hz,?2?H)?ppm;?
13C?NMR?(100?MHz,?DMSO-d6)?δ?166.2,?164.8,?164.1,?158.7,?137.2,?132.8,?132.6,?132.2,?and?132.3?ppm。
Infrared spectrum is shown in Fig. 5, and main peaks ownership is as follows: 3079(=C-H); 2919,2856(C-H); 2719 ~ 2520(carboxylic acid characteristic peak); 1706(C=O); 1602,1440(phenyl ring characteristic peak).
In above-mentioned specific embodiment, the consumption of each composition also can be selected lower value in numerical range given in technical scheme or any number in higher limit or numerical range.
5-[2-of the present invention (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid has advantages of that synthetic cost is low, productive rate is high, product purity is high.
Claims (7)
1. a 5-[2-(5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, is characterized in that: synthesis step is:
(I) is under the condition of argon gas or nitrogen protection, with the different peptide acid of 5-bromine two formicesters, connection boric acid pinacol ester and potassium acetate in molar ratio 1 ︰ 0.8～1.5 ︰ 2.8～3.5 are dissolved in dioxane after mixing, the amount ratio of the different peptide of 5-bromine acid two formicesters and dioxane is 1 rub in the least 2.6～2.8 milliliters of ︰, add appropriate catalyzer, under 110～130 ℃ of oil baths, back flow reaction is 10～35 hours, cooling rear first dilute with water extracts system with methylene dichloride again, then with strong brine, organic layer is washed, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, last take sherwood oil and ethyl acetate and as the mixed solvent of 10 ︰ 0.8～1.2 as eluent, with column chromatography separating-purifying, obtain target compound A:5-[2-(4 by volume, 4, 5, 5-tetramethyl--1, 3, 2-boric acid ether)]-1, 3-phenylformic acid dimethyl ester,
(II), under argon gas or nitrogen protection, the A that upper step is obtained and 2-chloropyrimide-5-carboxylic acid, ethyl ester in molar ratio 1.2 ︰ 1 mix and dissolve in K
2cO
3solution, ethanol and toluene is by volume in the mixed solvent of 1 ︰ 0.8～1.2 ︰ 2.8～3.2, A and K
2cO
3the amount ratio of solution is 0.6～0.9 milliliter of 1 Hao Mo ︰, add proper catalyst, under 90 ~ 110 ℃ of oil baths, react 10 ~ 40 hours, cooling rear first dilute with water extracts system with methylene dichloride again, collect organic phase and with anhydrous magnesium sulfate, it removed to water treatment, filter, vacuum concentration, then take methylene dichloride and acetone by volume as 99 ︰ 0.5～1.5 are eluent, with column chromatography separating-purifying, obtain white product, white product is hydrolyzed, being acidified to pH=2 white solid separates out, vacuum-drying obtains final compd B: 5-[2-(5-carboxyl-pyrimidyl)]-1, 3-benzene dicarboxylic acid.
2. a kind of 5-[2-according to claim 1 (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, is characterized in that: with the different peptide acid of 5-bromine two formicesters, connection boric acid pinacol ester and potassium acetate 1 ︰ 1 ︰ 3 synthetic compound A in molar ratio.
3. a kind of 5-[2-according to claim 2 (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, it is characterized in that: the catalyzer of preparing compd A use is [1,1 '-bis-(diphenylphosphine) diamyl iron] palladium chloride, consumption is for participating in 0.2～0.5% of reactant total mass.
4. a kind of 5-[2-according to claim 3 (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, is characterized in that: preparing compd B solvent for use is K
2cO
3solution, ethanol and toluene is the mixed solvent of 1 ︰ 1 ︰ 3 by volume, K
2cO
3the concentration of solution is 2 M.
5. a kind of 5-[2-according to claim 4 (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, it is characterized in that: while preparing compd B, used catalyst is tetra-triphenylphosphine palladium, consumption is for participating in 0.2～0.5% of reactant total mass.
6. a kind of 5-[2-according to claim 5 (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, is characterized in that: the eluent of using while preparing the separation of compd A column chromatography is that sherwood oil and ethyl acetate volume ratio are the mixed solvent of 10 ︰ 1.
7. a kind of 5-[2-according to claim 8 (5-carboxyl-pyrimidyl)]-1, the synthetic method of 3-benzene dicarboxylic acid, is characterized in that: the eluent of using while preparing the separation of compd B column chromatography is that methylene dichloride and acetone volume ratio are the mixed solvent of 99 ︰ 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310648660.6A CN103664796A (en) | 2013-12-06 | 2013-12-06 | Synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310648660.6A CN103664796A (en) | 2013-12-06 | 2013-12-06 | Synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103664796A true CN103664796A (en) | 2014-03-26 |
Family
ID=50303674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310648660.6A Pending CN103664796A (en) | 2013-12-06 | 2013-12-06 | Synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103664796A (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060258687A1 (en) * | 2005-03-25 | 2006-11-16 | Boehm Jeffrey C | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one derivatives |
| CN101356170A (en) * | 2005-11-08 | 2009-01-28 | 沃泰克斯药物股份有限公司 | Heterocyclic modulators of ATP-binding cassette transporters |
| US20090318424A1 (en) * | 2006-06-16 | 2009-12-24 | Mauro Corsi | Novel compounds |
| US20100144755A1 (en) * | 2006-06-16 | 2010-06-10 | Glaxo Group Limited | Novel Compounds |
| TW201026681A (en) * | 2008-12-15 | 2010-07-16 | Almirall Sa | New(3-oxo)pyridazin-4-ylurea derivatives |
| CN102125875A (en) * | 2011-01-20 | 2011-07-20 | 郑州大学 | Application of cyclopalladated ferrocenylimine-phosphine adduct in synthesis of asymmetric biaryl compound |
| CN102924720A (en) * | 2012-12-03 | 2013-02-13 | 吉林大学 | Boric acid ester-containing polyarylether sulphone material and preparation method thereof |
| CN103396355A (en) * | 2013-07-31 | 2013-11-20 | 华南理工大学 | Compound using tripyridylbenzene as core as well as preparation method and application thereof |
| CN103396404A (en) * | 2013-07-31 | 2013-11-20 | 华南理工大学 | Compound using triphenylpyrimidine as core as well as preparation method and application thereof |
-
2013
- 2013-12-06 CN CN201310648660.6A patent/CN103664796A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060258687A1 (en) * | 2005-03-25 | 2006-11-16 | Boehm Jeffrey C | Process for preparing pyrido[2,3-d]pyrimidin-7-one and 3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one derivatives |
| CN101356170A (en) * | 2005-11-08 | 2009-01-28 | 沃泰克斯药物股份有限公司 | Heterocyclic modulators of ATP-binding cassette transporters |
| US20090318424A1 (en) * | 2006-06-16 | 2009-12-24 | Mauro Corsi | Novel compounds |
| US20100144755A1 (en) * | 2006-06-16 | 2010-06-10 | Glaxo Group Limited | Novel Compounds |
| TW201026681A (en) * | 2008-12-15 | 2010-07-16 | Almirall Sa | New(3-oxo)pyridazin-4-ylurea derivatives |
| CN102125875A (en) * | 2011-01-20 | 2011-07-20 | 郑州大学 | Application of cyclopalladated ferrocenylimine-phosphine adduct in synthesis of asymmetric biaryl compound |
| CN102924720A (en) * | 2012-12-03 | 2013-02-13 | 吉林大学 | Boric acid ester-containing polyarylether sulphone material and preparation method thereof |
| CN103396355A (en) * | 2013-07-31 | 2013-11-20 | 华南理工大学 | Compound using tripyridylbenzene as core as well as preparation method and application thereof |
| CN103396404A (en) * | 2013-07-31 | 2013-11-20 | 华南理工大学 | Compound using triphenylpyrimidine as core as well as preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| TAE-HONG PARK,等: "Gas and liquid phase adsorption in isostructural Cu3[biaryltricarboxylate]2 microporous coordination polymers", 《CHEMICAL COMMUNICATIONS》, vol. 47, no. 5, 6 December 2010 (2010-12-06) * |
| XING DUAN,等: "A microporous metal–organic framework of a rare stytopology for high CH4 storage at room temperature", 《CHEMICAL COMMUNICATIONS》, vol. 49, no. 20, 28 January 2013 (2013-01-28) * |
| 高善云,等: "异噻唑酮取代的间苯二甲酸衍生物的设计、合成及其抑制β-分泌酶活性", 《中国药物化学杂志》, vol. 20, no. 06, 31 December 2010 (2010-12-31), pages 467 - 475 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Laval et al. | A mild and efficient method for the reduction of nitriles | |
| Ye et al. | Diverse Zn (II) MOFs assembled from V-shaped asymmetric multicarboxylate and N-donor ligands | |
| Wang et al. | Controlling structural topology of metal-organic frameworks with a desymmetric 4-connected ligand through the design of metal-containing nodes | |
| CN105001031B (en) | Ionic iron (III) coordination compound containing single phenol functionalization Imidazole cation and preparation method and application | |
| JP5209183B2 (en) | Method for producing 2-cyanophenylboronic acid or ester thereof with reduced impurities | |
| CN117105845A (en) | Electrophilic trifluoro methyl selenizing reagent and preparation method and application thereof | |
| CN106117225A (en) | The synthetic method of benzophenanthrene decane epoxide bridging isobutyltrimethylmethane. phenyl porphyrin metal Zn coordination compound | |
| CN103664796A (en) | Synthesis method of 5-[2-(5-carboxyl-pyrimidyl)]-1,3-benzene dicarboxylic acid | |
| Su et al. | Three transition metal complexes with uncoordinated carboxyl groups: Synthesis, structures, and luminescence properties | |
| CN105237337B (en) | The synthetic method of new 5 [10 (9 carboxyl anthryl)] M-phthalic acid | |
| Mao et al. | Synthesis of Novel Chiral Thioether Ligands Containing Imidazole Rings Based on Natural Amino Acids | |
| CN103664770A (en) | Synthesis method of 5-[2-(5-carboxyl-pyridyl)]-1,3-benzene dicarboxylic acid | |
| Zhu et al. | Two Gd (III) coordination polymers based on a flexible tricarboxylate: syntheses, structures, luminescence and catalytic properties | |
| CN102807504A (en) | Method for synthesizing salicylamide | |
| CN105418936A (en) | Lanthanide metal organic framework with polyrotaxane configuration as well as preparation method and application thereof | |
| CN105175297A (en) | Synthesis and application of 4-formyl benzoic acid adamantine ester condensed o-aminobenzene thiophenol schiff base nickel complex | |
| GB2466365A (en) | Phosphine-borane compounds | |
| CN102219739A (en) | Azaanthracene compound and synthesizing method thereof | |
| Kolodiazhna et al. | Synthesis and properties of four-membered phosphorus heterocycles-2-fluoro-1, 2λ5-oxaphosphetanes | |
| JP5407332B2 (en) | Method for producing quarterpyridine derivative and its intermediate | |
| CN107778146A (en) | A kind of synthetic method of ether compound | |
| CN104945346B (en) | Bay-position oxygen-intercalation aza-heptatomic ring 3, 4, 9, 10-perylene tetracarboxylic acid butyl acetate and synthesis method thereof | |
| CN102180858A (en) | Mono-substituted or di-substituted xanthone compound and synthetic method thereof | |
| CN103113297B (en) | 8-aryl-1-naphthylamide compound and preparation method thereof | |
| CN103910668B (en) | A kind of preparation method of 3 alkyl-indol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140326 |