CN107188843A - Utilize the method for carbonylation one pot process α glucosidase inhibitors - Google Patents
Utilize the method for carbonylation one pot process α glucosidase inhibitors Download PDFInfo
- Publication number
- CN107188843A CN107188843A CN201710461220.8A CN201710461220A CN107188843A CN 107188843 A CN107188843 A CN 107188843A CN 201710461220 A CN201710461220 A CN 201710461220A CN 107188843 A CN107188843 A CN 107188843A
- Authority
- CN
- China
- Prior art keywords
- compound
- carbonylation
- alpha
- glucosidase restrainer
- crude product
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Abstract
The method that the present invention relates to the use of carbonylation one pot process α glucosidase inhibitors.This method, through the condensation of amine aldehyde, oxidation carbonylation, the reduction of nitro, four reactions steps of sulfonating reaction, successfully synthesizes α glucosidase inhibitors using 4 nitrobenzaldehydes and n-butylamine as reaction raw materials.This method synthesizing mean is novel, successfully synthesizes α glucosidase inhibitors using carbonylation, reaction raw materials are simple and easy to get, and reaction condition is gentle, and simultaneous reactions have good atom economy and step economy, meet the demand for development of Green Chemistry.
Description
Technical field
The present invention relates to the technical field such as medicine, clinic, cell biology, and in particular to one pot of carbonylation of utilization
Method synthesizes the novel synthesis of alpha-glucosidase restrainer.
Background technology
Alpha-glucosidase restrainer is the oral hypoglycemic drug that a class is widely known by the people, by delaying enteron aisle carbohydrate
Absorption, reach treatment diabetes effect.By clinical research for many years, alpha-glucosidase restrainer has been developed as
The medicine of the ripe treatment diabetes of one class, its mechanism of action is the various alpha-glucosidases by suppressing small intestine, makes starch
The speed reduction of transforming glucose, so as to substantially lower postprandial hyperglycemia.The absorption of nutrition is not interfered with simultaneously, is not had to liver kidney yet
There is any side effect and cumulative effect.Just because of the significant pharmacology of alpha-glucosidase restrainer so that synthesis α-
Glucosidase inhibitor turns into a study hotspot in new drug development field.Under such research background, we utilize
A kind of alpha-glucosidase restrainer of carbonylation one pot process, its synthetic route is as follows：
The alpha-glucosidase restrainer that the present invention is synthesized, its structural formula is as follows：
The invention has synthesized alpha-glucosidase restrainer by carbonylation four step rule, is the synthesis of such compound
There is provided a new synthetic route, it is cheap and easy to get that the route sets the raw material being related to, and reaction condition is gentle, and route is ripe
The content of the invention
It the present invention relates to the use of the method that carbonylation four step rule synthesizes alpha-glucosidase restrainer.This method is with 4-
Nitrobenzaldehyde and n-butylamine are as reaction raw materials through the condensation of amine aldehyde, oxidation carbonylation, the reduction of nitro, sulfonating reaction four
Individual reactions steps, successfully synthesize alpha-glucosidase restrainer.This method has synthesizing mean novel, and raw material is cheap and easy to get etc.
Feature.
Technical solution of the present invention is as follows.
Using the method for carbonylation one pot process alpha-glucosidase restrainer, synthetic route is as follows：
In the above method, the alpha-glucosidase restrainer is by compound 1 and compound 2 through the condensation of amine aldehyde, oxidation carbonyl
Glycosylation reaction, the reduction of nitro, four reactions steps of sulfonating reaction are made；The compound 1 is 4- nitrobenzaldehydes；Describedization
Compound 2 is n-butylamine；
Comprise the following steps that：
(1) compound 1 and compound 2 are taken in test tube, catalyst, oxidant and solvent is added, 1- is stirred in 10-60 DEG C
48 hours, realize amine aldehyde condensation course；
(2) take step (1) to react the test tube after terminating, the balloon filled with carbon monoxide and oxygen gas is put, in 40-
Stir 1-72 hours, filter at 150 DEG C, extraction, through sand core funnel suction filtration, obtains the crude product of compound 3, realizes oxidation carbonyl
Change process；The volume ratio of the carbon monoxide and oxygen is 10:1-1:10；
(3) take the crude product of compound 3 to be dissolved in ethanol, reduced iron powder is added by several times, hydrochloric acid or acetic acid is added dropwise；Add afterwards
Ammoniacal liquor or sodium hydroxide solution adjust pH value to 7.1-10.0, and reaction is filtered after terminating, and extraction, through sand core funnel suction filtration, is obtained
The crude product of compound 4, realizes the reduction process of nitro；
(4) take the crude product of compound 4 to be dissolved in dichloromethane, add triethylamine, added under low temperature to Methyl benzenesulfonyl
Chlorine, realizes sulfonation process, and separating-purifying obtains alpha-glucosidase restrainer.
In the above method, the catalyst is palladium salt；The oxidant be oxygen, 1,4-benzoquinone, manganese dioxide, silver carbonate,
Copper acetate, cupric oxide or potassium peroxydisulfate；The solvent is molten for the mixing of toluene (PhMe) and N,N-dimethylformamide (DMF)
Agent；Wherein the mixed volume ratio of toluene (PhMe) and N,N-dimethylformamide (DMF) is 1：100~100：1.
In the above method, the mol ratio of the compound 1 and compound 2 is 1：(1~4).
In the above method, the addition of the catalyst is met：The mol ratio of catalyst and compound 1 for (0.05~
0.5):1；The addition of the oxidant is met：The mol ratio of oxidant and compound 1 is (1~4):1.
In the above method, the addition of the reduced iron powder is met：The crude product of the compound 3 and rubbing for reduced iron powder
You are than being 1：10~10:1；The addition of the hydrochloric acid or acetic acid is met：The crude product of the compound 3 and hydrochloric acid or acetic acid
Mol ratio is 1：10~10:1.
In the above method, the crude product of the compound 4 and the mol ratio of triethylamine are 1：10~10:1.
In the above method, the crude product of the compound 4 and the mol ratio of p-methyl benzene sulfonic chloride are 1：10~10:1.
In the above method, the balloon pressure filled with carbon monoxide and oxygen gas is 1~100 atmospheric pressure.
In the above method, reaction is isolated and purified product using column chromatography after terminating；The column chromatography eluent is oil
The mixed solvent of ether and ethyl acetate, the volume ratio between petroleum ether and ethyl acetate is 1~40:1.
Compared with prior art, advantage of the invention is that：
This method synthesizing mean is novel, and alpha-glucosidase restrainer is successfully synthesized using carbonylation, and reaction is former
Material is simple and easy to get, and reaction condition is gentle, and simultaneous reactions have good atom economy and step economy, meet Green Chemistry
Demand for development.
Brief description of the drawings
Fig. 1 is the proton nmr spectra of the alpha-glucosidase restrainer obtained in embodiment 1；
Fig. 2 is the carbon-13 nmr spectra of the alpha-glucosidase restrainer obtained in embodiment 1.
Embodiment
The invention is further described below by specific embodiment.
Embodiment 1
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 10:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1)
Balloon is as carbonyl source, in stirring 48 hours under 100 degrees Celsius.TLC (thin-layered chromatography) detection reactions terminate after by reaction solution
Room temperature is cooled to, balloon is removed, unreacted carbon monoxide and oxygen is slowly vented.Reacting liquid filtering, filtrate decompression revolving is gone
Except solvent, then obtain through sand core funnel suction filtration the crude product of compound 3；Take 0.2 mM of the crude product of compound 3, reduced iron
0.6 mM of powder, adds ethanol and is dissolved as solvent, add 1.2 mMs of HCl, and in being stirred at 100 DEG C, reaction terminates rear cold
But to room temperature, add NaOH and adjust PH to alkalescence, reaction is filtered after terminating, and extraction, through sand core funnel suction filtration, obtains compound 4
Crude product；Take 0.2 mM of the crude product of compound 4 to be dissolved in dichloromethane solvent, add 0.4 mM of triethylamine, in
0.3 mM of p-methyl benzene sulfonic chloride is slowly added under low temperature, reaction obtains target by column chromatographic isolation and purification after terminating and produced
Thing alpha-glucosidase restrainer, column chromatography eluent used is that volume ratio is 10：1 petroleum ether：Ethyl acetate mixing is molten
Agent, yield 29%.
The present embodiment structure of title compound is shown according to Fig. 1 and Fig. 2.
Embodiment 2
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) as solvent, in stirring 12 hours under normal temperature.Then
Put containing carbon monoxide and oxygen (volume ratio 1:1) balloon is as carbonyl source, in stirring 48 hours under 100 degrees Celsius.TLC
(thin-layered chromatography) tracing detection, does not detect compound 3.
Embodiment 3
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds DMF (DMF) as solvent, in stirring under normal temperature
12 hours.Then put containing carbon monoxide and oxygen (volume ratio 1:1) balloon is stirred as carbonyl source under 100 degrees Celsius
Mix 48 hours.TLC (thin-layered chromatography) tracing detection, does not detect compound 3.
Embodiment 4
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds acetonitrile (CH3CN) as solvent, in stirring 12 hours under normal temperature.So
Contain carbon monoxide and oxygen (volume ratio 1 in rear enclosure:1) balloon is as carbonyl source, in stirring 48 hours under 100 degrees Celsius.
TLC (thin-layered chromatography) tracing detection, does not detect compound 3.
Embodiment 5
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds Isosorbide-5-Nitrae-dioxane (dioxane) as solvent, in stirring under normal temperature
12 hours.Then put containing carbon monoxide and oxygen (volume ratio 1:1) balloon is stirred as carbonyl source under 100 degrees Celsius
Mix 48 hours.TLC (thin-layered chromatography) tracing detection, does not detect compound 3.
Embodiment 6
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds dimethyl sulfoxide (DMSO) (DMSO) as solvent, small in stirring 12 under normal temperature
When.Then put containing carbon monoxide and oxygen (volume ratio 1:1) balloon is as carbonyl source, in stirring 48 under 100 degrees Celsius
Hour.TLC (thin-layered chromatography) tracing detection, does not detect compound 3.
Embodiment 7
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 5:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1) gas
Ball is as carbonyl source, in stirring 48 hours under 100 degrees Celsius.TLC (thin-layered chromatography) tracing detection, is only able to detect trace
Compound 3.
Embodiment 8
The synthesis of alpha-glucosidase restrainer
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 1:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1) gas
Ball is as carbonyl source, in stirring 48 hours under 100 degrees Celsius.TLC (thin-layered chromatography) tracing detection, does not detect compound
3。
Embodiment 9
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 10:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1)
Balloon is as carbonyl source, in stirring 48 hours under normal temperature.TLC (thin-layered chromatography) tracing detection, does not detect compound 3.
Embodiment 10
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 10:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1)
Balloon is as carbonyl source, in stirring 48 hours under 80 degrees Celsius.TLC (thin-layered chromatography) tracing detection, does not detect chemical combination
Thing 3.
Embodiment 11
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 10:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1)
Balloon is as carbonyl source, in stirring 48 hours under 90 degrees Celsius.TLC (thin-layered chromatography) tracing detection, is only able to detect trace
Compound 3.
Embodiment 12
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 10:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1)
Balloon is as carbonyl source, in stirring 48 hours under 110 degrees Celsius.TLC (thin-layered chromatography) detection reactions terminate after by reaction solution
Room temperature is cooled to, balloon is removed, unreacted carbon monoxide and oxygen is slowly vented.Reacting liquid filtering, filtrate decompression revolving is gone
Except solvent, then obtain through sand core funnel suction filtration the crude product of compound 3；Take 0.2 mM of the crude product of compound 3, reduced iron
0.6 mM of powder, adds ethanol and is dissolved as solvent, add 1.2 mMs of HCl, and in being stirred at 100 DEG C, reaction terminates rear cold
But to room temperature, add NaOH and adjust PH to alkalescence, reaction is filtered after terminating, and extraction, through sand core funnel suction filtration, obtains compound 4
Crude product；Take 0.2 mM of the crude product of compound 4 to be dissolved in dichloromethane solvent, add 0.4 mM of triethylamine, in
0.3 mM of p-methyl benzene sulfonic chloride is slowly added under low temperature, reaction obtains target by column chromatographic isolation and purification after terminating and produced
Thing alpha-glucosidase restrainer, column chromatography eluent used is that volume ratio is 10：1 petroleum ether：Ethyl acetate mixing is molten
Agent, yield 13%.
Embodiment 13
0.2 mM of benzaldehyde, 0.2 mM of 2,6-DIPA, dichlorodiethyl are added in 25mL test tube
0.01 mM of nitrile palladium, 0.2 mM of cupric oxide adds toluene (PhMe) and DMF (DMF) as mixing
Solvent, volume ratio is 10:1, in stirring 12 hours under normal temperature.Then put containing carbon monoxide and oxygen (volume ratio 1:1)
Balloon is as carbonyl source, in stirring 48 hours under 120 degrees Celsius.TLC (thin-layered chromatography) detection reactions terminate after by reaction solution
Room temperature is cooled to, balloon is removed, unreacted carbon monoxide and oxygen is slowly vented.Reacting liquid filtering, filtrate decompression revolving is gone
Except solvent, then obtain through sand core funnel suction filtration the crude product of compound 3；Take 0.2 mM of the crude product of compound 3, reduced iron
0.6 mM of powder, adds ethanol and is dissolved as solvent, add 1.2 mMs of HCl, and in being stirred at 100 DEG C, reaction terminates rear cold
But to room temperature, add NaOH and adjust PH to alkalescence, reaction is filtered after terminating, and extraction, through sand core funnel suction filtration, obtains compound 4
Crude product；Take 0.2 mM of the crude product of compound 4 to be dissolved in dichloromethane solvent, add 0.4 mM of triethylamine, in
0.3 mM of p-methyl benzene sulfonic chloride is slowly added under low temperature, reaction obtains target by column chromatographic isolation and purification after terminating and produced
Thing alpha-glucosidase restrainer, column chromatography eluent used is that volume ratio is 10：1 petroleum ether：Ethyl acetate mixing is molten
Agent, yield 8%.
Test result in above-described embodiment is shown in Tables 1 and 2.
Table 1
| Solvent (solvent) | Yield (%) |
| PhMe | 0 |
| DMF | 0 |
| CH3CN | 0 |
| dioxane | 0 |
| DMSO | 0 |
| PhMe/DMF(10:1) | 29 |
| PhMe/DMF(5:1) | Trace |
| PhMe/DMF(1:1) | 0 |
Table 2
Solvent and the temperature parameter setting of the present invention can significantly improve reaction yield.Conjunction on such compound at present
Use single solvent as reaction dissolvent into majority, but it is of the invention when using single solvent as reaction dissolvent, all detect not
To target product, when only using toluene (PhMe) and DMF (DMF) instead as mixed solvent, reaction could be sent out
It is raw.And the proportioning of solvent also has a significant impact to reaction yield, only solvent ratios are PhMe/DMF (10:1) when, reaction
Effect is only best；In addition, temperature parameter of the invention setting can also significantly improve reaction yield.
Claims (10)
1. utilize the method for carbonylation one pot process alpha-glucosidase restrainer, it is characterised in that synthetic route is such as
Under：
2. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 1, it is special
Levy and be, the alpha-glucosidase restrainer is by compound 1 and compound 2 through the condensation of amine aldehyde, oxidation carbonylation, nitro
Reduction, four reactions steps of sulfonating reaction be made；The compound 1 is 4- nitrobenzaldehydes；The compound 2 is positive fourth
Amine；
Comprise the following steps that：
(1) compound 1 and compound 2 are taken in test tube, catalyst, oxidant and solvent is added, it is small to stir 1-48 in 10-60 DEG C
When, realize amine aldehyde condensation course；
(2) take step (1) to react the test tube after terminating, the balloon filled with carbon monoxide and oxygen gas is put, in 40-150 DEG C
Lower stirring 1-72 hours, is filtered, and extraction through sand core funnel suction filtration, obtains the crude product of compound 3, realizes oxidative carbonylation mistake
Journey；The volume ratio of the carbon monoxide and oxygen is 10:1-1:10；
(3) take the crude product of compound 3 to be dissolved in ethanol, reduced iron powder is added by several times, hydrochloric acid or acetic acid is added dropwise；Ammoniacal liquor is added afterwards
Or sodium hydroxide solution adjusts pH value to 7.1-10.0, reaction is filtered after terminating, and extraction, through sand core funnel suction filtration, obtains chemical combination
The crude product of thing 4, realizes the reduction process of nitro；
(4) take the crude product of compound 4 to be dissolved in dichloromethane, add triethylamine, it is real in adding p-methyl benzene sulfonic chloride under low temperature
Existing sulfonation process, separating-purifying obtains alpha-glucosidase restrainer.
3. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The catalyst is palladium salt；The oxidant is oxygen, 1,4-benzoquinone, manganese dioxide, silver carbonate, copper acetate, cupric oxide
Or potassium peroxydisulfate；The solvent is the mixed solvent of toluene (PhMe) and N,N-dimethylformamide (DMF)；Wherein toluene
(PhMe) and N,N-dimethylformamide (DMF) mixed volume ratio be 1：100~100：1.
4. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The mol ratio of the compound 1 and compound 2 is 1：(1~4).
5. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The addition of the catalyst is met：The mol ratio of catalyst and compound 1 is (0.05~0.5):1；The oxidation
The addition of agent is met：The mol ratio of oxidant and compound 1 is (1~4):1.
6. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The addition of the reduced iron powder is met：The crude product of the compound 3 and the mol ratio of reduced iron powder are 1：10~
10:1；The addition of the hydrochloric acid or acetic acid is met：The mol ratio of the crude product of the compound 3 and hydrochloric acid or acetic acid is 1：10
~10:1.
7. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The crude product of the compound 4 and the mol ratio of triethylamine are 1：10~10:1.
8. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The crude product of the compound 4 and the mol ratio of p-methyl benzene sulfonic chloride are 1：10~10:1.
9. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 2, it is special
Levy and be：The balloon pressure filled with carbon monoxide and oxygen gas is 1~100 atmospheric pressure.
10. utilizing the method for carbonylation one pot process alpha-glucosidase restrainer according to claim 1, it is special
Levy and be：Reaction is isolated and purified product using column chromatography after terminating；The column chromatography eluent is petroleum ether and ethyl acetate
Mixed solvent, volume ratio between petroleum ether and ethyl acetate is 1~40:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710461220.8A CN107188843A (en) | 2017-06-18 | 2017-06-18 | Utilize the method for carbonylation one pot process α glucosidase inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710461220.8A CN107188843A (en) | 2017-06-18 | 2017-06-18 | Utilize the method for carbonylation one pot process α glucosidase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107188843A true CN107188843A (en) | 2017-09-22 |
Family
ID=59879714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710461220.8A Pending CN107188843A (en) | 2017-06-18 | 2017-06-18 | Utilize the method for carbonylation one pot process α glucosidase inhibitors |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107188843A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108822002A (en) * | 2018-06-21 | 2018-11-16 | 中南大学 | A kind of method of ultrasonic wave added synthesis N- aryl sulfonic acid amides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104926711A (en) * | 2015-06-01 | 2015-09-23 | 华南理工大学 | Method for synthesizing TRPA1-like modifier precursor by use of carbonylation one-pot reaction |
| CN105130874A (en) * | 2015-07-25 | 2015-12-09 | 华南理工大学 | One-pot method for synthesizing N-substituted phthalimide through carbonylation |
-
2017
- 2017-06-18 CN CN201710461220.8A patent/CN107188843A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104926711A (en) * | 2015-06-01 | 2015-09-23 | 华南理工大学 | Method for synthesizing TRPA1-like modifier precursor by use of carbonylation one-pot reaction |
| CN105130874A (en) * | 2015-07-25 | 2015-12-09 | 华南理工大学 | One-pot method for synthesizing N-substituted phthalimide through carbonylation |
Non-Patent Citations (2)
| Title |
|---|
| BIAN, XIAOLI, ET AL.: ""A new series of N2-substituted-5-(p-toluenesulfonylamino) phthalimide analogues as α-glucosidase inhibitors"", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
| 及方华: ""钯催化一氧化碳参与的氧化羰基化反应研究"", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108822002A (en) * | 2018-06-21 | 2018-11-16 | 中南大学 | A kind of method of ultrasonic wave added synthesis N- aryl sulfonic acid amides |
| CN108822002B (en) * | 2018-06-21 | 2020-05-05 | 中南大学 | Method for synthesizing N-aryl sulfonamide under assistance of ultrasonic waves |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111423452B (en) | Intermediate of Rayleigh Lu Geli and preparation method and application thereof | |
| CN110183378B (en) | Nicotinamide derivative and catalytic synthesis method thereof | |
| CN108752284A (en) | Two amido-s- compound in triazine class of one kind and its preparation method and application | |
| CN105130999B (en) | A kind of synthetic method of Xi Gelieting impurity | |
| CN105884628A (en) | Preparation method of 2,4-ditertbutyl-5-aminophenol | |
| CN104926711B (en) | Utilize the method for carbonylation one pot process class TRPA1 conditioning agent precursors | |
| CN107188843A (en) | Utilize the method for carbonylation one pot process α glucosidase inhibitors | |
| CN107629051A (en) | A kind of method that rutaecarpin is synthesized using carbonylation three-step approach | |
| CN103130855A (en) | Preparation method of decitabine | |
| CN105924390B (en) | A kind of synthetic method of Mei Tafeini | |
| CN105272911B (en) | A kind of preparation method of Sorafenib Tosylate | |
| CN105949139B (en) | A kind of sec-butyl diphenyl tetrazine benzamide compound and preparation and application | |
| CN107188844A (en) | Utilize the method for the enzyme inhibitors of carbonylation one pot process COX 2 | |
| CN109369505A (en) | It is the method that three step of starting material constructs alpha-glucosidase restrainer using imines | |
| EP4177243A1 (en) | Preparation method for aromatic ether compound | |
| CN108558974B (en) | Preparation and application of sugar-derived nickel pyridine triazole catalyst | |
| CN111892553A (en) | Method for synthesizing ammonium acetate mediated benzothiazole compound | |
| CN107235889A (en) | Utilize the method for carbonylation one pot process TNF alpha inhibitors | |
| CN110467571A (en) | A method of preparing naphthenic base formic acid analog derivative or its officinal salt | |
| CN111440163B (en) | Pyrazole compound containing methoxy-substituted 1,3, 4-thiadiazole unit, and preparation and application thereof | |
| CN113292556B (en) | Preparation method and intermediate of alkynyl-containing compound | |
| CN109293557A (en) | It is the method that one step of starting material constructs TNF-α inhibitor using imines | |
| JP5279449B2 (en) | Process for producing 5- {4- [2- (5-ethyl-2-pyridyl) ethoxy] benzyl} -2,4-thiazolidinedione hydrochloride | |
| CN101245070A (en) | Novel technique for synthesizing toroid quinazoline protein tyrosine kinase restrainer | |
| CN109293556A (en) | It is the method that one step of starting material constructs COX-2 enzyme inhibitor using imines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170922 |