CN105418516A - Quinazoline compounds and preparation method thereof - Google Patents
Quinazoline compounds and preparation method thereof Download PDFInfo
- Publication number
- CN105418516A CN105418516A CN201510957056.0A CN201510957056A CN105418516A CN 105418516 A CN105418516 A CN 105418516A CN 201510957056 A CN201510957056 A CN 201510957056A CN 105418516 A CN105418516 A CN 105418516A
- Authority
- CN
- China
- Prior art keywords
- aryl
- quinazoline compounds
- preparation
- alkyl
- substituted aryl
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
Abstract
The invention discloses quinazoline compounds which have a specific structural formula as shown in the description, wherein R1 is aryl, substituted aryl or alkyl; R2 is fluorine, chlorine or methyl; R3 is aryl, substituted aryl or alkyl. By taking amino acid and nitroacetophenone compounds as raw materials for reaction, under the catalytic action of recyclable palladium/carbon (Pd/C), good compatibility for water and air can be realized by stirring and heating in solvent, and further the quinazoline compounds can be obtained. According to the method, no oxidants, reducing agents, ligands and alkaline additives are needed to be added, reaction conditions are mild, and scale production is easily realized. Experimental results show that the yield of obtained quinazoline compounds can be as high as 92 percent.
Description
Technical field
The present invention relates to the field of chemical synthesis, be specially a kind of quinazoline compounds and preparation method thereof.
Background technology
Quinazoline compounds is present in occurring in nature in a large number, comprises biomacromolecule, and in drug molecule and natural product, it is the most important organic compound type of a class.Quinazoline compounds is of many uses, can as agricultural chemicals, spices, and the intermediate of medicine, monomer (J.Med.Chem., 2004,47,871 of the bioactive moleculess such as synthetic protein and functional materials; J.Med.Chem., 2006,49,6015).
Due to the importance of quinazoline compound, therefore receive the concern widely of region of chemistry and organic sphere and medical circle.But regrettably, traditional method is exactly can a step form quinoline compound (Chem.Commun., 2010,46,5244 by oxidative condensation by o-aminoacetophenone and benzylamine etc. under strong oxidizer exists; Chem.Commun., 2011,47,7818 – 7820; Angew.Chem.Int.Ed.2012,51,8077 – 8081).These methods all will use some excessive oxygenants, and as tertbutyl peroxide, these oxygenants easily explode, to bringing some unsafe factors in actual production process.Simultaneously maximum problem is that product out prepared by these methods is often confined to 2-aryl-quinazoline, and the quinazolines replaced for 2 fat just can not get.Therefore greatly have impact on the prospect of its application.
Therefore, improving existing quinazoline compounds and preparation method thereof, greatly improve its Application Areas, has been a urgent problem.
Summary of the invention
In order to overcome above-mentioned deficiency of the prior art, the invention provides a kind of starting raw material using amino acid and o-nitroacetophenone compound as reaction, being easy to quinazoline compounds realizing scale operation and preparation method thereof.Reaction conditions is gentle, can compatible water and air well, does not need to add any oxygenant, reductive agent, part and alkaline additive, only needs stirring heating in a solvent can obtain the quinazoline compounds of various replacement by high productivity.
The object of the present invention is achieved like this:
A kind of quinazoline compounds, its concrete structure formula is:
Wherein, R
1for aryl, substituted aryl, alkyl; R
2for fluorine, chlorine, methyl; R
3for aryl, substituted aryl, alkyl.
The preparation method of described quinazoline compounds is:
A) will have the amino acid of structure (I) and the o-nitroacetophenone compound of structure (II) and palladium-carbon catalyst, dispersion in a solvent;
B) mixture obtained to step a) is 90-140
oreact 8-24h at C temperature, obtain the quinazoline compounds containing structure (III);
。
Described R
1during for aryl, described aryl is phenyl or naphthyl;
Described R
1during for substituted aryl, described substituted aryl be rubigan, p-methylphenyl, 3,4-Dimethoxyphenyls, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, p-trifluoromethyl phenyl, to tert-butyl-phenyl, to fluorophenyl, to ethyl formate phenyl or to bromophenyl;
Described R
1during for alkyl, described R
1for methyl, n-propyl, the tertiary butyl or cyclohexyl;
Described R
2for fluorine, chlorine or methyl;
Described R
3during for aryl, phenyl can be divided.
Described R
3during for substituted aryl, described substituted aryl is to fluorophenyl, to bromophenyl, rubigan, p-methylphenyl;
Described R
3during for alkyl, described alkyl is the tertiary butyl, cyclopentyl or n-hexadecyl;
Described catalyzer is commercially available various palladium carbon (Pd/C);
Described o-nitroacetophenone compound and amino acid whose mol ratio are 1:1-1:3;
The mol ratio of described o-nitroacetophenone compound and palladium carbon is 20:1-200:1;
The solvent of described reaction is acetonitrile, toluene, DMF, methyl-sulphoxide, dioxane or water;
Described temperature of reaction is 90-140
oc;
The described reaction times is 8-24h.
Positive beneficial effect: compared with existing the field of chemical synthesis correlation technique; the present invention achieves with o-nitroacetophenone compound and Amino acid synthesis quinazoline compounds and preparation method thereof first time; in this method; do not need to add any oxygenant, reductive agent, part and alkaline additive; and reaction conditions is gentle; good compatibility can be had to water and air, be easy to accomplish scale production.Experimental result shows, the productive rate of the quinazoline compounds of acquisition can up to 92%.
Accompanying drawing explanation
Fig. 1 a is according to the embodiment of the present invention 1, the proton nmr spectra of the 4-methyl-2-phenylquinazoline of 2,3,4,5,6 preparations;
Fig. 1 b is according to the embodiment of the present invention 1, the carbon-13 nmr spectra of the 4-methyl-2-phenylquinazoline of 2,3,4,5,6 preparations;
Fig. 2 a is the 4-methyl-2-(4-chloro-phenyl-prepared according to the embodiment of the present invention 7) proton nmr spectra of-quinazoline.
Fig. 2 b is the 4-methyl-2-(4-chloro-phenyl-prepared according to the embodiment of the present invention 7) carbon-13 nmr spectra of-quinazoline;
Fig. 3 a is the proton nmr spectra of the 2-phenylquinazoline according to the embodiment of the present invention 8 preparation;
The carbon-13 nmr spectra of the 2-phenylquinazoline that Fig. 3 b is prepared according to the embodiment of the present invention 8;
Fig. 4 a is the 4-methyl-2-(4-fluorophenyl prepared according to the embodiment of the present invention 9) proton nmr spectra of-quinazoline;
Fig. 4 b is the 4-methyl-2-(4-fluorophenyl prepared according to the embodiment of the present invention 9) carbon-13 nmr spectra of-quinazoline;
Fig. 5 a is the proton nmr spectra of 2, the 4-dimethyl quinazolines according to the embodiment of the present invention 10 preparation;
Fig. 5 b is the carbon-13 nmr spectra of 2, the 4-dimethyl quinazolines according to the embodiment of the present invention 10 preparation;
Fig. 6 a is the proton nmr spectra of 2, the 4-phenylbenzene quinazolines according to the embodiment of the present invention 11 preparation;
Fig. 6 b is the carbon-13 nmr spectra of 2, the 4-phenylbenzene quinazolines according to the embodiment of the present invention 11 preparation;
Fig. 7 a is the proton nmr spectra of 4, the 6-dimethyl-2-phenylquinazolines according to the embodiment of the present invention 12 preparation;
Fig. 7 b is the carbon-13 nmr spectra of 4, the 6-dimethyl-2-phenylquinazolines according to the embodiment of the present invention 12 preparation.
Embodiment
Below in conjunction with drawings and Examples, the present invention is described further:
A kind of quinazoline compounds, its concrete structure formula is:
Wherein, R
1for aryl, substituted aryl or alkyl; R
2for fluorine, chlorine or methyl; R
3for aryl, substituted aryl or alkyl.
The preparation method of described a kind of quinazoline compounds, comprises the following steps:
A) amino acid of structure (I) and structure (II) o-nitroacetophenone compound will be had under the katalysis of palladium carbon, by stirring heating in a solvent, the quinazoline compounds of the present invention with structure (III) can be obtained:
Wherein, R
1for aryl, substituted aryl or alkyl; R
2for fluorine, chlorine or methyl; R
3for aryl, substituted aryl or alkyl.
R
1for aryl, described aryl is phenyl or naphthyl; Described R
1for substituted aryl, described substituted aryl be rubigan, p-methylphenyl, 3,4-Dimethoxyphenyls, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, p-trifluoromethyl phenyl, to tert-butyl-phenyl, to fluorophenyl, to ethyl formate phenyl or to bromophenyl; Described R
1for alkyl, described alkyl is methyl, n-propyl, the tertiary butyl or cyclohexyl.
Described R
2for fluorine, chlorine or methyl.
Described R
3during for aryl, described aryl comprises phenyl; Described R
3for substituted aryl, described substituted aryl is to fluorophenyl, to bromophenyl, rubigan or p-methylphenyl; Described R
3for alkyl, described alkyl comprises the tertiary butyl, cyclopentyl or n-hexadecyl.
Described o-nitroacetophenone compound and amino acid whose mol ratio are 1:1-1:3.
Described o-nitroacetophenone compound and palladium carbon mol ratio are 20:1-200:1; The solvent of described reaction is acetonitrile, toluene, DMF, methyl-sulphoxide, dioxane or water.
Described temperature of reaction is 90
oc-140
oc.
The described reaction times is 8-24h.
Embodiment 1
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C4.09 milligram, solvent made by ortho-nitroacetophenone 40 milligrams, phenylglycine 113 milligrams, 1 milliliter of toluene successively, load onto condensing reflux pipe, 130 under nitrogen protection
oc reacts 24 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 49.5 milligrams of white solids, productive rate 90%.
As shown in Figure 1a, carbon-13 nmr spectra as shown in Figure 1 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-phenylquinazoline.
Embodiment 2
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C13.25 milligram, solvent made by ortho-nitroacetophenone 40 milligrams, phenylglycine 110 milligrams, 1 milliliter of toluene successively, load onto condensing reflux pipe, 120 under nitrogen protection
oc reacts 24 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 47 milligrams of white solids, productive rate 85%.
As shown in Figure 1a, carbon-13 nmr spectra as shown in Figure 1 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-phenylquinazoline.
Embodiment 3
In 10 milliliters of Schlenk reaction tubess of a clean dried, adding massfraction is successively 10%Pd/C10.25 milligram, ortho-nitroacetophenone 40 milligrams, phenylglycine 113 milligrams, 1 milliliter of water as solvent, loads onto condensing reflux pipe, 100 under nitrogen protection
oc reacts 24 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 33 milligrams of white solids, productive rate 60%.
As shown in Figure 1a, carbon-13 nmr spectra as shown in Figure 1 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-phenylquinazoline.
Embodiment 4
In 10 milliliters of Schlenk reaction tubess of a clean dried, adding massfraction is successively 10%Pd/C10.25 milligram, ortho-nitroacetophenone 40 milligrams, phenylglycine 98 milligrams, 1 milliliter of water as solvent, loads onto condensing reflux pipe, 140 under nitrogen protection
oc reacts 18 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 51 milligrams of white solids, productive rate 92%.
As shown in Figure 1a, carbon-13 nmr spectra as shown in Figure 1 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-phenylquinazoline.
Embodiment 5
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C5.5 milligram, ortho-nitroacetophenone 40 milligrams, phenylglycine 120 milligrams, 1 milliliter of DMF make solvent successively, load onto condensing reflux pipe, 120 under nitrogen protection
oc reacts 24 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 48 milligrams of white solids, productive rate 88%.
As shown in Figure 1a, carbon-13 nmr spectra as shown in Figure 1 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-phenylquinazoline.
Embodiment 6
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C6.0 milligram, ortho-nitroacetophenone 40 milligrams, phenylglycine 110 milligrams, 1 milliliter of dioxane make solvent successively, load onto condensing reflux pipe, 130 under nitrogen protection
oc reacts 10 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 46 milligrams of white solids, productive rate 84%.
As shown in Figure 1a, carbon-13 nmr spectra as shown in Figure 1 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-phenylquinazoline.
Embodiment 7
In 10 milliliters of Schlenk reaction tubess of a clean dried; add that massfraction is 10%Pd/C4.05 milligram, ortho-nitroacetophenone 40 milligrams, p-chlorophenylglycine 140 milligrams, 1 milliliter of dioxane make solvent successively; load onto condensing reflux pipe, 130 under nitrogen protection
oc reacts 10 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 30:1) is dissolved, cross post by short silicagel column to be separated, obtain 57 milligrams of white solids, productive rate 89%.
As shown in Figure 2 a, carbon-13 nmr spectra as shown in Figure 2 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-(4-chloro-phenyl-)-quinazoline.
Embodiment 8
In 10 milliliters of Schlenk reaction tubess of a clean dried, adding massfraction is successively 10%Pd/C4.05 milligram, Ortho Nitro Benzaldehyde 38 milligrams, phenylglycine 113 milligrams, 1 milliliter of water as solvent, loads onto condensing reflux pipe, 130 under nitrogen protection
oc reacts 18 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 10:1) is dissolved, cross post by short silicagel column to be separated, obtain 31 milligrams of white solids, productive rate 60%.
As shown in Figure 3 a, carbon-13 nmr spectra as shown in Figure 3 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is to 2-phenylquinazoline.
Embodiment 9
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C4.5 milligram successively, ortho-nitroacetophenone 40 milligrams, to fluorophenyl glycine 113 milligrams, 1 milliliter of water as solvent, load onto condensing reflux pipe, 130 under nitrogen protection
oc reacts 12 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 25:1) is dissolved, cross post by short silicagel column to be separated, obtain 53 milligrams of white solids, productive rate 89%.
As shown in fig. 4 a, carbon-13 nmr spectra as shown in Figure 4 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4-methyl-2-(4-fluorophenyl)-quinazoline.
Embodiment 10
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C4.5 milligram, solvent made by ortho-nitroacetophenone 40 milligrams, the third glycine 67 milligrams, 1 milliliter of toluene successively, load onto condensing reflux pipe, 140 under nitrogen protection
oc reacts 24 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, and filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 3:1) is dissolved, and crosses post and is separated, obtain 24 milligrams of white solids, productive rate 62% by short silicagel column.
As shown in Figure 5 a, carbon-13 nmr spectra as shown in Figure 5 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 2,4-dimethyl quinazoline.
Embodiment 11
In 10 milliliters of Schlenk reaction tubess of a clean dried, add that massfraction is 10%Pd/C4.5 milligram, solvent made by adjacent nitro benzophenone 57 milligrams, phenylglycine 113 milligrams, 1 milliliter of toluene successively, load onto condensing reflux pipe, 140 under nitrogen protection
oc reacts 18 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 40:1) is dissolved, cross post by short silicagel column to be separated, obtain 55 milligrams of white solids, productive rate 78%.
As shown in Figure 6 a, carbon-13 nmr spectra as shown in Figure 6 b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 2,4-phenylbenzene quinazoline.
Embodiment 12
In 10 milliliters of Schlenk reaction tubess of a clean dried; adding massfraction is successively 10%Pd/C4.5 milligram, 5-methyl-2-nitro-acetophenone 45 milligrams, phenylglycine 113 milligrams, 1 milliliter of water as solvent; load onto condensing reflux pipe, 130 under nitrogen protection
oc reacts 20 hours.After reaction terminates, by filtering, the catalyzer of recovery can directly recycle next time, filtrate is directly spin-dried for a small amount of sherwood oil of rear use and ethyl acetate (volume ratio is 40:1) is dissolved, cross post by short silicagel column to be separated, obtain 54 milligrams of white solids, productive rate 90%.
As shown in Figure 7a, carbon-13 nmr spectra as shown in Figure 7b for the proton nmr spectra of product prepared by the present embodiment.Can confirm from collection of illustrative plates, the product of acquisition is 4,6-dimethyl-2-phenylquinazoline.
In one embodiment, the preparation method of a kind of quinazoline compounds provided by the invention, wherein by o-nitroacetophenone compound and amino acid, and palladium catalyst carbon, dispersion is in a solvent; By the reaction mixture that obtains by stirring heating, obtain corresponding quinazoline compounds.
In the present invention, under the katalysis of palladium carbon, can there is a depickling and dehydrogenation reaction in described amino acid easily, generates active intermediate PdH
2this intermediate can be easy to ortho-nitroacetophenone to be reduced into o-aminoacetophenone, and then with generate the condensation reaction of imines generation twice dehydration, generate intermediate product dihydroquinazoline, this intermediate product can again under the katalysis of palladium carbon through dehydrogenation oxidation, generate last product quinazoline.In whole catalytic cycle, ortho-nitroacetophenone is the acceptor of hydrogen, and amino acid is then the donor of hydrogen and carbonic acid gas.The advantage of the method clearly, without any need for oxygenant, reductive agent, part and alkaline additive, this reaction can be carried out smoothly.
Above-mentioned is explanation to the preferred embodiment of the invention, realize to enable those skilled in the art or use the present invention, apparent to some amendments of these embodiments concerning those skilled in the art, General Principle as defined herein can not depart from the scope of the present invention or under mental condition, realize in other embodiments.Therefore, the scope of the invention is not by the restriction of above-mentioned specific embodiment.
Claims (10)
1. a quinazoline compounds, is characterized in that, its concrete structure formula is:
Wherein, R
1for aryl, substituted aryl or alkyl; R
2for fluorine, chlorine or methyl; R
3for aryl, substituted aryl or alkyl.
2. the preparation method of a kind of quinazoline compounds as claimed in claim 1, is characterized in that, comprise the following steps:
A) amino acid of structure (I) and structure (II) o-nitroacetophenone compound will be had under the katalysis of palladium carbon, by stirring heating in a solvent, the quinazoline compounds of the present invention with structure (III) can be obtained:
Wherein, R
1for aryl, substituted aryl or alkyl; R
2for fluorine, chlorine or methyl; R
3for aryl, substituted aryl or alkyl.
3. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: R
1for aryl, described aryl is phenyl or naphthyl; Described R
1for substituted aryl, described substituted aryl be rubigan, p-methylphenyl, 3,4-Dimethoxyphenyls, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, p-trifluoromethyl phenyl, to tert-butyl-phenyl, to fluorophenyl, to ethyl formate phenyl or to bromophenyl; Described R
1for alkyl, described alkyl is methyl, n-propyl, the tertiary butyl or cyclohexyl.
4. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: described R
2for fluorine, chlorine or methyl.
5. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: described R
3during for aryl, described aryl comprises phenyl; Described R
3for substituted aryl, described substituted aryl is to fluorophenyl, to bromophenyl, rubigan or p-methylphenyl; Described R
3for alkyl, described alkyl comprises the tertiary butyl, cyclopentyl or n-hexadecyl.
6. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: described o-nitroacetophenone compound and amino acid whose mol ratio are 1:1-1:3.
7. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: described o-nitroacetophenone compound and palladium carbon mol ratio are 20:1-200:1.
8. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: the solvent of described reaction is acetonitrile, toluene, DMF, methyl-sulphoxide, dioxane or water.
9. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: described temperature of reaction is 90
oc-140
oc.
10. the preparation method of a kind of quinazoline compounds according to claim 2, is characterized in that: the described reaction times is 8-24h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510957056.0A CN105418516B (en) | 2015-12-21 | 2015-12-21 | A kind of quinazoline compounds and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510957056.0A CN105418516B (en) | 2015-12-21 | 2015-12-21 | A kind of quinazoline compounds and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105418516A true CN105418516A (en) | 2016-03-23 |
| CN105418516B CN105418516B (en) | 2018-03-02 |
Family
ID=55497121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510957056.0A Expired - Fee Related CN105418516B (en) | 2015-12-21 | 2015-12-21 | A kind of quinazoline compounds and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105418516B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108976173A (en) * | 2016-12-30 | 2018-12-11 | 江西师范大学 | A kind of preparation method of 4- aryl -2- (2- (sulphur trifluoromethyl) aryl) quinazoline |
| CN111620824A (en) * | 2020-06-24 | 2020-09-04 | 武汉理工大学 | Method for synthesizing quinazoline compound by taking aromatic aldehyde as substrate |
| CN112125900A (en) * | 2020-09-29 | 2020-12-25 | 常州工程职业技术学院 | Synthesis method of isoquinoline quinazolinone compound |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675223A (en) * | 2012-04-28 | 2012-09-19 | 清华大学 | Preparation method for polysubstitution quinazoline and heterocyclic ring pyrimidine derivative |
| CN102675222A (en) * | 2012-04-28 | 2012-09-19 | 清华大学 | Method for preparing multi-substituted quinazoline and heterocyclic pyrimidine derivative |
| CN105327703A (en) * | 2014-08-08 | 2016-02-17 | 中国科学技术大学 | Preparation method for gold nanometer catalyst, and obtained catalyst product and application thereof |
-
2015
- 2015-12-21 CN CN201510957056.0A patent/CN105418516B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102675223A (en) * | 2012-04-28 | 2012-09-19 | 清华大学 | Preparation method for polysubstitution quinazoline and heterocyclic ring pyrimidine derivative |
| CN102675222A (en) * | 2012-04-28 | 2012-09-19 | 清华大学 | Method for preparing multi-substituted quinazoline and heterocyclic pyrimidine derivative |
| CN105327703A (en) * | 2014-08-08 | 2016-02-17 | 中国科学技术大学 | Preparation method for gold nanometer catalyst, and obtained catalyst product and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| HUAMIN WANG，等: "Palladium-catalyzed one pot 2-arylquinazoline formation via hydrogen-transfer strategy", 《ORG. BIOMOL. CHEM.》 * |
| JIA JU，等: "Copper-catalyzed three-component one-pot synthesis of quinazolines", 《TETRAHEDRON》 * |
| MADHAV BANDARU，等: "Simple and straight forward synthesis of 2,4‐disubstituted quinazolines in aqueous medium", 《EUROPEAN JOURNAL OF CHEMISTRY》 * |
| WANG ZHIYONG，等: "Supported gold-catalyzed and ammonia-promoted selective synthesis of quinazolines in aqueous media", 《ORG. CHEM. FRONT.》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108976173A (en) * | 2016-12-30 | 2018-12-11 | 江西师范大学 | A kind of preparation method of 4- aryl -2- (2- (sulphur trifluoromethyl) aryl) quinazoline |
| CN108976173B (en) * | 2016-12-30 | 2022-01-18 | 江西师范大学 | Preparation method of 4-aryl-2- (2- (sulfur trifluoromethyl) aryl) quinazoline |
| CN111620824A (en) * | 2020-06-24 | 2020-09-04 | 武汉理工大学 | Method for synthesizing quinazoline compound by taking aromatic aldehyde as substrate |
| CN111620824B (en) * | 2020-06-24 | 2023-08-22 | 武汉理工大学 | Method for synthesizing quinazoline compound by taking aromatic aldehyde as substrate |
| CN112125900A (en) * | 2020-09-29 | 2020-12-25 | 常州工程职业技术学院 | Synthesis method of isoquinoline quinazolinone compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105418516B (en) | 2018-03-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Akram et al. | Ligand-enabled gold-catalyzed C (sp2)–N cross-coupling reactions of aryl iodides with amines | |
| Zhang et al. | Asymmetric synthesis of chiral P-stereogenic triaryl phosphine oxides via Pd-catalyzed kinetic arylation of diaryl phosphine oxides | |
| Pu et al. | Doubly stereocontrolled asymmetric conjugate addition of acetylacetone to nitroolefins catalyzed by bifunctional tertiary amine–thiourea catalysts derived from both acyclic α-amino acids and carbohydrates | |
| CN105418516A (en) | Quinazoline compounds and preparation method thereof | |
| CN105017082A (en) | Preparation method of cardiotonic drug Entresto key intermediate (R)-tert-butyl-(1-([1,1'-biphenyl]-4-yl)-3-hydroxypropane-2-yl)carbamate | |
| Moberg | Mechanism of Diphenylprolinol Silyl Ether Catalyzed Michael Addition Revisited—but Still Controversial | |
| CN101219399B (en) | Preparation method and application of N-heterocyclic carbine metal palladium catalyst | |
| Pahadi et al. | Aza-Henry reaction of ketimines catalyzed by guanidine and phosphazene bases | |
| Zott et al. | Mechanism of a Luminescent Dicopper System That Facilitates Electrophotochemical Coupling of Benzyl Chlorides via a Strongly Reducing Excited State | |
| CN103433076A (en) | Immobilized asymmetric catalyst and application thereof in asymmetric hydrogenation reaction | |
| Wei et al. | Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction | |
| CN109847806B (en) | Polyion liquid-cerium oxide catalyst and preparation method and application thereof | |
| CN106518726A (en) | Aryl Schiff base derivative and preparation method and application thereof | |
| CN101848916A (en) | Titanium compound and process for asymmetric cyanation of imines | |
| CN105777662A (en) | Benzoxazole and benzimidazole compounds and preparation method thereof | |
| JP5426556B2 (en) | Method for asymmetric cyanation of imine | |
| CN101186587A (en) | Method for synthesizing derivative of beta-amino acid and intermediate product thereof | |
| CN103301883B (en) | N,N-bis-schiff base type oxovanadium (IV) complex catalyst and preparation method as well as application method thereof | |
| CN101698664A (en) | Preparation method of pharmaceutical intermediate 2-amine methylpyrazine hydrochloride | |
| CN107298683B (en) | A kind of synthetic method of chirality benzodiazepine * compound | |
| CN103232410B (en) | Method for preparing 2-amino benzothiazine | |
| CN103467390B (en) | Method for preparing 2-amino-4(3H)-quinazolinones | |
| CN102584651B (en) | Reduction method of sulfoacid | |
| CN102531978B (en) | Preparation method of thiophenol | |
| CN106905264B (en) | A method of synthesis A Zhalawei intermediate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB03 | Change of inventor or designer information |
Inventor after: Tang Lin Inventor after: Tang Wenbin Inventor after: Tan Meirong Inventor after: Yang Die Inventor before: Tang Lin |
|
| CB03 | Change of inventor or designer information | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180302 Termination date: 20191221 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |