CN103242223A - Preparation method of 2-pyridineoxydiaryl ketone derivative - Google Patents
Preparation method of 2-pyridineoxydiaryl ketone derivative Download PDFInfo
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- CN103242223A CN103242223A CN2013101537635A CN201310153763A CN103242223A CN 103242223 A CN103242223 A CN 103242223A CN 2013101537635 A CN2013101537635 A CN 2013101537635A CN 201310153763 A CN201310153763 A CN 201310153763A CN 103242223 A CN103242223 A CN 103242223A
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- pyridyloxy
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- diaryl ketone
- silver
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- SUUAKNHJWCYAPX-UHFFFAOYSA-N COc(cc1)cc(C(c2ccccc2)=O)c1Oc1ncccc1 Chemical compound COc(cc1)cc(C(c2ccccc2)=O)c1Oc1ncccc1 SUUAKNHJWCYAPX-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N COc1ccc(C(c2ccccc2)=O)c(O)c1 Chemical compound COc1ccc(C(c2ccccc2)=O)c(O)c1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a preparation method of 2-pyridineoxydiaryl ketone derivative. The preparation method comprises the following steps of: adding a catalyst, an oxidant, a 2-pyridineoxydiaryl compound and aryl oxoacetic acid to an organic solvent; heating up to 90-120 DEG C; and posttreating to obtain 2-pyridineoxydiaryl ketone derivative after the reaction is completed. The preparation method of the pyridineoxydiaryl ketone derivative disclosed by the invention is easy to operate, simple in posttreatment, strong in substrate designability, capable of designing a compound for synthesizing the needed structure according to actual needs, and stronger in practicability. Meanwhile, the compound prepared by the preparation method is good in bioactivity, can be used as the material for synthesizing various 2-pyridineoxydiaryl ketone derivative compounds and is higher in economic value.
Description
Technical field
The invention belongs to the organic synthesis field, be specifically related to a kind of preparation method of 2-pyridyloxy diaryl ketone derivatives.
Background technology
2-pyridyloxy diaryl ketone is the very important organic intermediate of a class, and it extensively is present in the natural product as a kind of important nitrogen heterocyclic ring.For example the mother nucleus structure of the multiple resistive connection intestinal cancer compound that extracts in the yellow fruit of tonkin tinomiscium stem is exactly the diaryl ketone.（Bioactive?Benzophenonesfrom?Garcinia?xanthochymus?Fruits,J.Nat.Prod.2005,68,354-360）
The functionalization of deriving of this compounds has caused a large amount of study on the synthesis persons' interest.For example its derivative can be used as the non-nucleoside reverse transcriptase inhibitor (NNRTI) of anti-HIV-1. (Practical snthesis of a benzophenone-based NNRT inhibitor of HIV-1, Org.Process Res.Dev.2012,16,561-566)
In addition, 2-pyridyloxy diaryl ketone will produce 2-hydroxyl diaryl methanone compounds through hydrolysis, and hydrolytic process is simple, easy handling and realization industrialization.2-hydroxyl diaryl methanone compounds is very important organic raw material, it can be used as the raw material of more synthetic medicines, for example patent application WO2012041860A1 discloses the method for the synthetic class indole derivatives of a kind of 2-of use dihydroxy benaophenonel, and such indole derivatives can be used as a kind of histamine H
4Receptor antibody.
Summary of the invention
The invention provides a kind of preparation method of 2-pyridyloxy diaryl ketone derivatives, this method steps is simple, and the by product of reaction is carbonic acid gas and water, and environmental pollution is little.
A kind of preparation method of 2-pyridyloxy diaryl ketone derivatives, comprise: with catalyzer, oxygenant, 2-pyridyloxy aryl compound and aryl formyl formic acid join in the organic solvent, be heated to 90～120 ℃, reacting completely obtains described 2-pyridyloxy diaryl ketone derivatives by aftertreatment;
The structure of described 2-pyridyloxy aryl compound is suc as formula shown in (II):
The structure of described aryl formyl formic acid is suc as formula shown in (III):
The structure of described 2-pyridyloxy diaryl ketone derivatives is suc as formula shown in (I):
Among formula (I)-Shi (III): R
1Be hydrogen, halogen, C
1～C
5Alkyl or C
1～C
5Alkoxyl group;
R
2Be hydrogen, halogen, C
1～C
5Alkyl, C
1～C
5Alkoxyl group or trifluoromethyl;
Described catalyzer is the divalence palladium catalyst;
Described oxygenant is monovalence silver oxygenant.
Above-mentioned reaction process is shown below:
As shown in Figure 1, preparation method's of the present invention possible reaction mechanism is as follows: described divalence palladium catalyst and 2-pyridyloxy diaryl ketone derivatives are (with R
1=H is example) in pyridine N atom carry out coordination after, generation intermediate A in activation back takes place in the ortho position c h bond to the 2-pyridyloxy, form intermediate B after intermediate A and the aryl formyl formic acid generation metal exchange, and then generation decarboxylic reaction, generate intermediate C, reduction takes place intermediate C eliminates the described 2-pyridyloxy diaryl ketone derivatives of generation, and discharges the zeroth order palladium, the zeroth order palladium regenerates the divalence palladium catalyst under the effect of oxygenant then, finishes catalytic cycle.Among this preparation method, by product was water and carbonic acid gas after reaction was finished, and environmental pollution is little, and reaction raw materials becomes more readily available, and cost is lower.
As preferably, described R
1Be hydrogen, fluorine, chlorine, bromine, methyl or methoxy, at this moment, these 2-pyridyloxy aryl compounds (II) can select for use existing method to prepare, and for example can select for use 2-bromopyridine and fragrant phenol to obtain under the effect of monovalence copper and alkali.
As further preferred, described R
2Be hydrogen, fluorine, chlorine, bromine, methyl, methoxyl group or trifluoromethyl, this moment, raw material aryl formyl formic acid cheaply was easy to get, and reaction yield is higher.
As preferably, described organic solvent is dioxane, acetic acid or methyl-sulphoxide, and the consumption of reaction solvent does not have strict especially requirement, raw material fully can be dissolved to get final product.
As preferably, described divalence palladium catalyst comprises palladium, dichloro diacetonitrile palladium (Pd (CH
3CN)
2Cl
2) or Palladous chloride, these divalence palladium catalysts can both be buied easily from the market.
As preferably, described monovalence silver oxygenant is Silver monoacetate, silver carbonate, silver suboxide or Silver Nitrate, and these oxygenants can both be buied easily from the market.
In the above-mentioned reaction, for economizing in raw materials, guarantee carrying out fully of reaction simultaneously, as preferably, the mol ratio of described 2-pyridyloxy aryl compound, aryl formyl formic acid, catalyzer and oxygenant is 1:2-4:0.1-0.3:1-3.
The reaction degree of carrying out can be by the TLC(thin-layer chromatography) monitor, as preferably, the reaction times is 6-12 hour, long increase reaction cost of reaction times, opposite then be difficult to guarantee to react complete.
As further preferred, described divalence palladium catalyst is dichloro diacetonitrile palladium;
Described monovalence silver oxygenant is silver suboxide;
Temperature of reaction is 110～115 ° of C, and at this moment, the productive rate of reaction is the highest, and side reaction is minimum.
As preferably, described 2-pyridyloxy diaryl ketone derivatives is selected from shown in formula (I-1)-Shi (I-10) a kind of in the compound:
（I-4）
After above-mentioned reaction was finished, available last handling process comprised: filter, silica gel mixed sample obtains corresponding 2-pyridyloxy diaryl ketone derivatives finally by crossing column chromatography purification.
The preparation method of 2-pyridyloxy diaryl ketone derivatives of the present invention, easy handling, aftertreatment is easy, and the substrate designability is strong, can design the compound that synthesizes desired structure according to actual needs, and practicality is stronger.Simultaneously, the compound biological activity that is obtained by method for preparing is good, can be used as the synthetic various 2-hydroxyl diaryl methanone compounds of raw material simultaneously, has higher economic value.
Description of drawings
Fig. 1 is the preparation method's of 2-pyridyloxy diaryl ketone derivatives of the present invention reaction mechanism figure.
Embodiment
Embodiment 1～10
Proportioning raw materials according to table 1 adds catalyzer, oxygenant, 2-pyridyloxy aryl compound (II), aryl formyl formic acid (III) and organic solvent 2ml in the Schlenk of 35ml pipe, mixing and stirring, after finishing according to the reaction of the reaction conditions of table 2, filter, silica gel mixed sample, obtain corresponding 2-pyridyloxy diaryl ketone derivatives (I) through column chromatography (eluent is sherwood oil) purifying, reaction process is shown below:
Table 1
Table 2
In table 1 and the table 2, T is temperature of reaction, and t is the reaction times, and Me is methyl, and OMe is methoxyl group, and p represents para-orientation, and m represents that the ortho position replaces.
Application examples 1
(CAS number: preparation 117-99-7): (138mg 0.5mmol) is dissolved in 5 milliliters the toluene compound (I-1) that embodiment 1 is prepared the 2-dihydroxy benaophenonel, adds 0.1mL trifluoromethanesulfonic acid methyl esters.Be heated to 100 ° of C, react 2 hours stopped reaction, revolve except toluene.Residue is dissolved in 5 milliliters the methyl alcohol, (270mg 5mmol), is heated to 80 ° of C reactions 0.5 hour to add sodium methylate.The reaction solution cool to room temperature, water and ethyl acetate layering, organic phase is collected, the saturated common salt water washing, anhydrous magnesium sulfate drying filters, and be spin-dried for and namely obtain product 2-dihydroxy benaophenonel 81mg, productive rate 82%, the nuclear magnetic data of products obtained therefrom is as follows:
1H?NMR(400MHz,CDCl
3,TMS)δ12.1(s,1H),7.69-7.67(m,2H),7.61-7.58(m,2H),7.51-7.49(m,3H),7.08(d,J=8.4Hz,1H),6.90-6.86(m,1H);
13C?NMR(100MHz,CDCl
3)δ201.6,163.2,137.8,136.3,133.6,131.9,129.1,128.3,119.1,118.6,118.4.
Application examples 2
(CAS number: preparation 131-57-7): (153mg 0.5mmol) is dissolved in 5 milliliters the toluene compound (I-9) that embodiment 9 is prepared 4-methoxyl group-2-dihydroxy benaophenonel, adds 0.1mL trifluoromethanesulfonic acid methyl esters.Be heated to 100 ° of C, react 2 hours stopped reaction, revolve except toluene.Residue is dissolved in 5 milliliters the methyl alcohol, (270mg 5mmol), is heated to 80 ° of C reactions 0.5 hour to add sodium methylate.The reaction solution cool to room temperature, water and ethyl acetate layering, organic phase is collected, the saturated common salt water washing, anhydrous magnesium sulfate drying filters, and be spin-dried for and namely obtain product 2-dihydroxy benaophenonel 96mg, productive rate 84%, the nuclear magnetic data of products obtained therefrom is as follows:
1H?NMR(400MHz,CDCl
3,TMS)δ12.20(s,1H),7.69-7.54(m,2H),7.56-7.51(m,1H),7.47-7.43(m,2H),7.15(d,J=8.0Hz,1H),7.06(d,J=8.0Hz,1H),6.78-6.76(m,1H),3.89(s,3H);
13C?NMR(100MHz,CDCl
3)δ201.6,153.2,148.8,137.7,131.8,128.1,124.6,124.3,119.1,117.9,116.9,56.1.
Embodiment 1～10 prepares the structural confirmation data of compound:
The structure detection data of the 2-pyridyloxy diaryl ketone derivatives that is prepared by embodiment 1～10 are respectively:
The 2-pyridyloxy diaryl ketone derivatives that is prepared by embodiment 1 (I-1, CAS number: nucleus magnetic resonance 1173294-85-3) (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.01(d,J=4.0Hz,1H),7.75(d,J=8.0Hz,2H),7.59-7.45(m,4H),7.35-7.28(m,4H),6.87(t,J=6.4Hz,1H),6.60(d,J=8.4Hz,1H);
13C?NMR(100MHz,CDCl
3)δ195.3,162.8,151.5,146.9,139.3,137.4,132.7,132.1,130.2,129.7,127.9,124.6,122.7,118.4,111.4.
The 2-pyridyloxy diaryl ketone derivatives that is prepared by embodiment 2 (I-2, CAS number: nucleus magnetic resonance 1173294-97-7) (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.01(d,J=4.0Hz,1H),7.67(d,J=8.0Hz,2H),7.56-7.49(m,3H),7.31-7.24(m,2H),7.13(d,J=8.4Hz,2H),6.86(t,J=7.2Hz,1H),6.64(d,J=8.4Hz,1H),2.35(s,3H);
13C?NMR(100MHz,CDCl
3)δ194.5,162.9,151.4,146.9,143.6,139.2,134.7,132.4,131.7,130.0,129.9,128.7,124.5,122.6,118.4,111.4,21.6.
The nucleus magnetic resonance of the 2-pyridyloxy diaryl ketone derivatives (I-3) that is prepared by embodiment 3 (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.01(d,J=4.0Hz,1H),7.55-7.51(m,3H),7.33-7.27(m,3H),7.25-7.19(m,2H),7.01(d,J=8.0,4.0Hz,1H),6.87(d,J=8.0Hz,1H),6.62(d,J=8.0Hz,1H),3.75(s,3H);
13C?NMR(100MHz,CDCl
3)δ195.0,162.9,159.3,151.5,146.9,139.3,138.7,132.1,132.0,130.1,128.9,124.5,122.9,122.7,119.6,118.4,113.1,111.4,55.3.
The nucleus magnetic resonance of the 2-pyridyloxy diaryl ketone derivatives (I-4) that is prepared by embodiment 4 (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.00(d,J=4.0Hz,1H),7.78(d,J=8.4,2.8Hz,2H),7.59-7.51(m,3H),7.31(t,J=7.6Hz,1H),7.25(d,J=7.6Hz,1H),6.99(t,J=8.8Hz,2H),6.88(t,J=6.4Hz,1H),6.62(d,J=8.4Hz,1H);
13C?NMR(100MHz,CDCl
3)δ193.7,165.5(J=253Hz),162.7,151.4,146.9,139.4,133.7(J=2.0Hz),132.4(J=8.9Hz),132.2,131.9,130.0,124.7,122.6,118.6,115.1(J=21.5Hz),111.4.
The nucleus magnetic resonance of the 2-pyridyloxy diaryl ketone derivatives (I-5) that is prepared by embodiment 5 (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.01(d,J=4.4Hz,1H),7.70(d,J=7.2Hz,2H),7.59-7.52(m,3H),7.34-7.25(m,4H),6.89(t,J=6.4Hz,1H),6.62(d,J=8.0Hz,1H);
13C?NMR(100MHz,CDCl
3)δ194.1,162.7,151.5,146.9,139.4,139.1,135.8,132.4,131.7,131.1,130.1,128.3,124.8,122.7,118.6,111.5.
The 2-pyridyloxy diaryl ketone derivatives that is prepared by embodiment 6 (I-6, CAS number: nucleus magnetic resonance 1173294-98-8) (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.00(d,J=4.0Hz,1H),7.63-7.53(m,5H),7.46(d,J=8.8Hz,2H),7.31(t,J=7.6Hz,1H),7.26-7.24(m,1H),6.89(t,J=5.6Hz,1H),6.62(d,J=8.8Hz,1H);
13C?NMR(125MHz,CDCl
3)δ194.2,162.7,151.5,146.9,139.4,136.2,132.4,131.6,131.3,131.2,130.1,127.8,124.7,122.7,118.6,111.5.
The nucleus magnetic resonance of the 2-pyridyloxy diaryl ketone derivatives (I-7) that is prepared by embodiment 7 (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.00-7.98(m,2H),7.93(d,J=8.0Hz,1H),7.70(d,J=8.0Hz,1H),7.61-7.59(m,2H),7.50-7.46(m,2H),7.35(t,J=7.2Hz,1H),7.28-7.26(m,1H),6.90-6.87(m,1H),6.55(d,J=8.0Hz,1H);
13C?NMR(100MHz,CDCl
3)δ194.0,162.6,151.7,147.0,139.4,138.3,132.8(2C),131.2,130.6(q,J=33.4Hz),130.1,129.0(q,J=3.7Hz),128.6,126.5(q,J=3.4Hz),124.9,123.6(q,J=265Hz),122.8,118.7,111.3.
The nucleus magnetic resonance of the 2-pyridyloxy diaryl ketone derivatives (I-8) that is prepared by embodiment 8 (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.01(d,J=4.0Hz,1H),7.74(d,J=7.6Hz,2H),7.48-7.44(m,2H),7.38-7.36(m,2H),7.31(t,J=7.6Hz,2H),7.15(d,J=8.8Hz,1H),6.85(t,J=6.8Hz,1H),6.55(d,J=8.0Hz,1H),2.40(s,3H);
13C?NMR(100MHz,CDCl
3)δ195.5,163.1,149.2,146.9,139.1,137.5,134.5,132.8,132.6,131.9,130.5,129.8,127.9,122.6,118.2,111.2,20.8.
The 2-pyridyloxy diaryl ketone derivatives that is prepared by embodiment 9 (I-9, CAS number: nucleus magnetic resonance 1173294-88-6) (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.01(d,J=5.2Hz,1H),7.74(d,J=8.0Hz,2H),7.48-7.44(m,2H),7.31(t,J=7.6Hz,2H),7.19(d,J=8.8Hz,1H),7.12-7.07(m,2H),6.84(t,J=6.4Hz,1H),6.52(d,J=8.4Hz,1H),3.83(s,3H);
13C?NMR(100MHz,CDCl
3)δ195.0,163.3,156.3,146.9,144.8,139.1,137.3,132.9,132.8,129.7,127.9,124.1,118.1,118.0,114.4,111.0,55.7.
The nucleus magnetic resonance of the 2-pyridyloxy diaryl ketone derivatives (I-10) that is prepared by embodiment 10 (
1H NMR and
13C NMR) detecting data is:
1H?NMR(400MHz,CDCl
3,TMS)δ8.00(d,J=3.6Hz,1H),7.75(d,J=7.2Hz,2H),7.53-7.48(m,2H),7.34(t,J=8.0Hz,2H),7.28-7.26(m,3H),6.88(t,J=6.0Hz,1H),6.58(d,J=8.4Hz,1H);
13C?NMR(100MHz,CDCl
3)δ193.8,162.8,159.0(J=245.3Hz),147.2(J=3.2Hz),146.8,139.4,136.8,133.5(J=7.2Hz),133.1,129.7,128.1,124.6(J=8.9Hz),118.8(J=23.9Hz),118.5,116.6(J=24.6Hz),111.3。
Claims (10)
1. the preparation method of a 2-pyridyloxy diaryl ketone derivatives, it is characterized in that, comprise: catalyzer, oxygenant, 2-pyridyloxy aryl compound and aryl formyl formic acid are joined in the organic solvent, be heated to 90～120 ℃, reacting completely obtains described 2-pyridyloxy diaryl ketone derivatives by aftertreatment;
The structure of described 2-pyridyloxy aryl compound is suc as formula shown in (II):
The structure of described aryl formyl formic acid is suc as formula shown in (III):
（III）；
The structure of described 2-pyridyloxy diaryl ketone derivatives is suc as formula shown in (I):
Among formula (I)-Shi (III), R
1Be hydrogen, halogen, C
1～C
5Alkyl or C
1～C
5Alkoxyl group;
R
2Be hydrogen, halogen, C
1～C
5Alkyl, C
1～C
5Alkoxyl group or trifluoromethyl;
Described catalyzer is the divalence palladium catalyst;
Described oxygenant is monovalence silver oxygenant.
2. the preparation method of 2-pyridyloxy diaryl ketone derivatives according to claim 1 is characterized in that described R
1Be hydrogen, fluorine, chlorine, bromine, methyl or methoxy.
3. the preparation method of 2-pyridyloxy diaryl ketone derivatives according to claim 2 is characterized in that described R
2Be hydrogen, fluorine, chlorine, bromine, methyl, methoxyl group or trifluoromethyl.
4. according to the preparation method of each described 2-pyridyloxy diaryl ketone derivatives of claim 1～3, it is characterized in that described organic solvent is dioxane, acetic acid or methyl-sulphoxide.
5. according to the preparation method of each described 2-pyridyloxy diaryl ketone derivatives of claim 1～3, it is characterized in that described divalence palladium catalyst comprises palladium, dichloro diacetonitrile palladium or Palladous chloride.
6. according to the preparation method of each described 2-pyridyloxy diaryl ketone derivatives of claim 1～3, it is characterized in that described monovalence silver oxygenant is Silver monoacetate, silver carbonate, silver suboxide or Silver Nitrate.
7. according to the preparation method of each described 2-pyridyloxy diaryl ketone derivatives of claim 1～3, it is characterized in that the mol ratio of described 2-pyridyloxy aryl compound, aryl formyl formic acid, catalyzer and oxygenant is 1:2-4:0.1-0.3:1-3.
8. according to the preparation method of each described 2-pyridyloxy diaryl ketone derivatives of claim 1～3, it is characterized in that the reaction times is 6-12 hour.
9. according to the preparation method of each described 2-pyridyloxy diaryl ketone derivatives of claim 1～3, it is characterized in that described divalence palladium catalyst is dichloro diacetonitrile palladium;
Described monovalence silver oxygenant is silver suboxide;
Temperature of reaction is 100～115 ° of C.
10. the preparation method of 2-pyridyloxy diaryl ketone derivatives according to claim 9 is characterized in that, described 2-pyridyloxy diaryl ketone derivatives is selected from shown in formula (I-1)-Shi (I-10) a kind of in the compound:
（I-10）。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418393A (en) * | 2015-11-27 | 2016-03-23 | 陕西师范大学 | Two-step one-pot synthesis method for meta-substituted diphenyl ketone compound |
| CN107879911A (en) * | 2017-10-25 | 2018-04-06 | 绍兴文理学院 | A kind of method that aromatic ketone is prepared in aqueous phase |
-
2013
- 2013-04-27 CN CN201310153763.5A patent/CN103242223B/en not_active Expired - Fee Related
Non-Patent Citations (3)
| Title |
|---|
| JINZHONG YAO，等: "Palladium-Catalyzed Decarboxylative Coupling of α-Oxocarboxylic Acids with C(sp2)-H of 2-Aryloxypyridines", 《ADV. SYNTH. CATAL.》 * |
| MINGZONG LI等: "Decarboxylative Acylation of Arenes with α-Oxocarboxylic Acids via Palladium-Catalyzed C-H Activation", 《ORGANIC LETTERS》 * |
| PING FANG,等: "Room Temperature Palladium-Catalyzed Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids", 《J. AM. CHEM. SOC.》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418393A (en) * | 2015-11-27 | 2016-03-23 | 陕西师范大学 | Two-step one-pot synthesis method for meta-substituted diphenyl ketone compound |
| CN105418393B (en) * | 2015-11-27 | 2018-07-10 | 陕西师范大学 | Two step one-pot synthesis methods of meta position substituted benzophenone class compound |
| CN107879911A (en) * | 2017-10-25 | 2018-04-06 | 绍兴文理学院 | A kind of method that aromatic ketone is prepared in aqueous phase |
| CN107879911B (en) * | 2017-10-25 | 2020-12-18 | 绍兴文理学院 | Method for preparing aromatic ketone in water phase |
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