CN108409628A - A kind of preparation method of alpha-aromatic nitrile compound - Google Patents
A kind of preparation method of alpha-aromatic nitrile compound Download PDFInfo
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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Abstract
The invention discloses a kind of preparation methods of α aryl nitrile compound, including：In the presence of anhydride compound, aryl sulfoxid es shown in structural formula (I) are reacted in a solvent with the nitrile compounds that α tin shown in structural formula (II) replaces, α aryl nitrile compounds shown in composite structure formula (III).This method synthesizes α aryl nitrile compounds in a mild condition by the nitrile compounds of aryl sulfoxid es and the substitution of α tin.This method reaction condition is mild, selectivity is good, and high income, product are easily separated, easy to operate.
Description
Technical field
The invention belongs to organic chemical synthesis fields, and in particular to a kind of preparation method of alpha-aromatic nitrile compound.
Background technology
Alpha-aromatic nitrile compound is the important structural unit in many natural products, drug.And cyano is with good
Functional group is derivative, thus as important organic synthesis.Simply it can be hydrolyzed or restore, prepare amide
(Inorg.Chim.Acta 2005,358,1-21), carboxylic acid (Tetrahedron Lett.2014,55,3802-3804.), aldehyde
(Tetrahedron Lett.2002,43,1395-1396.), ketone (J.Org.Chem.1987,52,3901-3904.) and amine
(J.Med.Chem.1993,36,3300-3307.) class compound.
In addition, alpha-aromatic nitrile compound is also widely present in biological medicine.The medicine of the structure of nitrile compound containing alpha-aromatic
Object can be used for treating a variety of diseases.For example, diphenoxylate：Drug for treating diarrhea；Anastrozole：For treating breast cancer
Drug；Verapamil：Drug for treating coronary heart disease；Gallopamil：The methoxy derivatives of Anastrozole, effectiveness are Ah those
10 times of bent azoles；Levocabastine：Drug for treating conjunctivitis；Different yellow enzyme element：A kind of analgesia pectoral.Therefore, it prepares
The synthetic method of alpha-aromatic nitrile compound has important practical significance.
Currently, the synthetic method of the alpha-aromatic nitrile compound of report is mainly the following：(1), aryl under basic conditions
The coupling reaction (Tetrahedron.1974,30,3723-3735) of halide and cyano compound.Although the reaction can be suitable
The alpha-aromatic nitrile compound of the synthesizing nitryl of profit, but regrettably the reaction substrate range is relatively narrow and needs highly basic body
It could be completed in system；(2), the cyanogenation (J.Org.Chem.1999,64,3171- of benzyl alcohol or benzylic halides
3177), although the reaction yield is higher, the advantages that also avoiding doing cyanogen source using the metal cyanides of severe toxicity, this reaction needs
The application of such reaction is but again limited the shortcomings that could be carried out under being heated to certain temperature.(3), palladium chtalyst aryl halide
The coupling reaction (Angew.Chem.Int.Ed.2003,42,5051-5053) of compound and cyano compound, the reaction need
It could be carried out under catalyzing by metal palladium, therefore condition limits the diversity of this reaction substrate, restricted application.
Invention content
In order to overcome defect existing in the prior art, the present invention provides a kind of preparation sides of alpha-aromatic nitrile compound
Method has reaction condition mild, and selectivity is good, and high income, product is easily separated, simple operation and other advantages.
The technical solution adopted by the present invention is as follows：
A kind of preparation method of alpha-aromatic nitrile compound, in the presence of anhydride compound, aryl shown in structural formula (I)
Sulfoxide is reacted in a solvent with the nitrile compounds that alpha tin shown in structural formula (II) replaces, shown in composite structure formula (III)
Alpha-aromatic nitrile compound, the general formula of the reaction is as follows：
Wherein, R1Selected from hydrogen, halogen, alkyl, alkoxy, alkyl-carbonyl, cyano or nitro, R2Selected from p-toluenesulfonyl
Or tertbutyloxycarbonyl, R3、R4With X independently selected from hydrogen or alkyl, m=3.
Preferably, in structural formula (I)~(III), R1Selected from hydrogen, halogen, C1~C4Alkyl, C1~C4Alkoxy, C1~C4Alkane
Base carbonyl or cyano, R2Selected from p-toluenesulfonyl or tertbutyloxycarbonyl, R3And R4Independently selected from hydrogen or C1~C4Alkyl, X are
C1~C4Alkyl, m=3.
The anhydride compound is trifluoroacetic anhydride, trifluoromethanesulfanhydride anhydride, methanesulfonic acid acid anhydride, p-toluenesulfonic anhydride, trichlorine
At least one of acetic anhydride, acetic anhydride, chloro difluoro acetic acid acid anhydride and glutaric anhydride.
Anhydride compound and the molar ratio that adds of aryl sulfoxid es are 1.1~2：1；Preferably, anhydride compound with
The molar ratio that adds of aryl sulfoxid es is 1.5：1.
The molar ratio that adds of aryl sulfoxid es and the nitrile compounds of alpha tin substitution is 1：1.1~2；Preferably, aryl is sub-
The molar ratio that adds of sulfone and the nitrile compounds of alpha tin substitution is 1：1.5.
Solvent for use of the present invention is acetonitrile or dichloromethane.
The temperature of the reaction is -80~0 DEG C, and the reaction time is 10min~15h.
Compared with the conventional method, the nitrile compounds that this method is replaced by aryl sulfoxid es with alpha tin close in a mild condition
At alpha-aromatic nitrile compound, it is advantageous that：
(1) the method for the present invention reaction condition is mild, and selectivity is good, and high income, product is easily separated, easy to operate；
(2) this method is raw materials used cheap and easy to get, and it is too strong to avoid conventional method neutral and alkali, reaction condition require it is stringent,
The shortcomings that reaction substrate is restricted；
(3) aryl sulfoxid es are reacted with the nitrile compounds that alpha tin replaces, and can be prepared chemically stable alpha-aromatic nitrilation and be closed
Object, the synthesis for this kind of compound provide new response strategy.
Specific implementation mode
Embodiment 1
- 78 DEG C, N2Under protection, the steamed 2.5mL dichloromethane (DCM) of weight is added in the reaction tube of 25ml, then will be fragrant
Base sulfoxide 167mg (0.5mmol) and the nitrile compounds 280mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoro second
Acid anhydrides (TFAA) 158mg (0.75mmol) stirs 12h, tracks reaction process with thin-layered chromatography, saturation is added after reaction
Reaction is quenched in sodium bicarbonate solution (3ml), is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract, and organic phase is used
Anhydrous sodium sulfate is dried, and is concentrated in vacuo, and (Rf=0.27, solvent are detached by column chromatography：Petrol ether/ethyl acetate=10/
1, v/v) product, obtained is white solid 178mg, yield 90%.
The mechanism of reaction involved by the present embodiment is as follows：
Target product is characterized as below：
1H NMR(600MHz,CDCl3) δ 8.19 (d, J=8.4Hz, 1H), 7.67 (t, J=6.6Hz, 3H), 7.40 (t, J
=7.8Hz, 1H), 7.34 (t, J=7.5Hz, 1H), 7.23 (d, J=8.3Hz, 2H), 5.25 (dd, J=9.2,6.2Hz, 1H),
2.33 (d, 7H), 1.99-1.87 (m, 1H), 1.74-1.63 (m, 1H), 1.53-1.42 (m, 1H), 1.00 (t, J=7.4Hz,
3H)。
13C NMR(151MHz,CDCl3)δ145.84,137.02,136.61,135.03,130.56,130.25,
126.63,126.22,124.60,119.83,119.25,118.74,115.73,36.04,28.84,21.74,20.97,
18.27,13.46。
Embodiment 2
- 78 DEG C, N2Under protection, the steamed 2.5mL dichloromethane of weight is added in the reaction tube of 25ml, then by aryl sulfoxid es
205.5mg (0.5mmol) and the nitrile compounds 280mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoroacetic anhydride
158mg (0.75mmol) stirs 12h, and reaction process is tracked with thin-layered chromatography, and it is molten that saturated sodium bicarbonate is added after reaction
Reaction is quenched in liquid (3ml), is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract, organic phase anhydrous sodium sulfate
It is dry, it is concentrated in vacuo, (Rf=0.23, solvent is detached by column chromatography:Petrol ether/ethyl acetate=20/1, v/v), it obtains
The product arrived is white solid 203mg, yield 85%.
Target product is characterized as below：
1H NMR(400MHz,CDCl3) δ 8.20 (d, J=8.4Hz, 1H), 7.68 (d, J=7.5Hz, 2H), 7.48 (d, J
=7.8Hz, 1H), 7.30-7.22 (m, 2H), 7.19 (t, J=8.2Hz, 1H), 5.38 (t, 1H), 2.38 (d, J=23.8Hz,
7H), 1.98-1.83 (m, 1H), 1.80-1.64 (m, 1H), 1.57-1.43 (m, 1H), 1.01 (t, J=7.3Hz, 3H).
13C NMR(151MHz,CDCl3)δ146.15,139.87,137.77,134.59,130.29,129.90,
127.68,126.58,126.47,119.11,118.52,114.68,114.52,35.87,28.93,21.67,21.27,
20.94,13.38。
Embodiment 3
- 40 DEG C, N2Under protection, the steamed acetonitrile (MeCN) of 2.5mL weights is added in the reaction tube of 25ml, then aryl is sub-
Sulfone 180.5mg (0.5mmol) and the nitrile compounds 280mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoroacetic acid
Acid anhydride 158mg (0.75mmol) stirs 12h, tracks reaction process with thin-layered chromatography, saturated sodium bicarbonate is added after reaction
Reaction is quenched in solution (3ml), is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract, organic phase anhydrous slufuric acid
Sodium is dried, and is concentrated in vacuo, and (Rf=0.23, solvent are detached by column chromatography:Petrol ether/ethyl acetate=10/1, v/v),
Obtained product is white solid 189mg, yield 89%.
Target product is characterized as below：
1H NMR(600MHz,CDCl3) δ 11.52 (s, 1H), 8.48 (d, J=7.5Hz, 1H), 7.96 (d, J=7.6Hz,
1H), 7.68 (s, 2H), 7.48 (t, J=8.0Hz, 1H), 7.27 (d, 2H), 5.42-5.30 (m, 1H), 2.35 (d, J=
22.3Hz, 7H), 1.99-1.86 (m, 1H), 1.80-1.69 (m, 1H), 1.57-1.43 (m, 1H), 1.02 (t, J=7.3Hz,
3H)。
13C NMR(151MHz,CDCl3)δ191.14,146.47,140.82,137.33,134.63,130.55,
130.49,129.97,126.66,125.68,124.00,120.96,118.84,116.77,35.90,28.93,21.79,
21.05,19.00,13.44。
Embodiment 4
- 78 DEG C, N2Under protection, the steamed 2.5mL dichloromethane of weight is added in the reaction tube of 25ml, then by aryl sulfoxid es
181.5mg (0.5mmol) and the nitrile compounds 280mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoroacetic anhydride
158mg (0.75mmol) stirs 12h, and reaction process is tracked with thin-layered chromatography, and it is molten that saturated sodium bicarbonate is added after reaction
Reaction is quenched in liquid (3ml), is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract, organic phase anhydrous sodium sulfate
It is dry, it is concentrated in vacuo, (Rf=0.24, solvent is detached by column chromatography:Petrol ether/ethyl acetate=10/1, v/v), it obtains
The product arrived is white solid 206mg, yield 96%.
Target product is characterized as below：
1H NMR(600MHz,CDCl3) δ 8.08 (d, J=9.1Hz, 1H), 7.64 (d, J=7.8Hz, 2H), 7.20 (d, J
=8.2Hz, 2H), 7.07 (d, J=2.5Hz, 1H), 6.99 (dd, J=9.1,2.6Hz, 1H), 5.23 (dd, J=9.2,
6.3Hz, 1H), 3.85 (s, 3H), 2.31 (d, J=9.1Hz, 7H), 1.99-1.85 (m, 1H), 1.72-1.59 (m, 1H),
1.53-1.38 (m, 1H), 0.99 (t, J=7.4Hz, 3H).
13C NMR(151MHz,CDCl3)δ157.34,145.66,137.65,134.76,131.76,130.90,
130.09,126.46,119.17,118.67,116.78,115.17,101.66,55.72,35.93,28.74,21.61,
20.84,18.07,13.36。
Embodiment 5
- 78 DEG C, N2Under protection, the steamed 2.5mL dichloromethane of weight is added in the reaction tube of 25ml, then by aryl sulfoxid es
179mg (0.5mmol) and the nitrile compounds 280mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoroacetic anhydride
158mg (0.75mmol) stirs 10min, is warming up to -60 DEG C, stirs 12h, and reaction process, reaction knot are tracked with thin-layered chromatography
Saturated sodium bicarbonate solution (3ml) is added after beam, reaction is quenched, is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract
It takes, organic phase is dried with anhydrous sodium sulfate, is concentrated in vacuo, and (Rf=0.28, solvent are detached by column chromatography:Petroleum ether/second
Acetoacetic ester=5/1, v/v), obtained product is white solid 208mg, yield 95%.
Target product is characterized as below：
1H NMR(600MHz,CDCl3) δ 8.30 (d, J=8.6Hz, 1H), 8.01 (s, 1H), 7.69 (d, J=6.8Hz,
2H), 7.64 (d, J=8.7Hz, 1H), 7.29 (d, J=8.2Hz, 2H), 5.19 (dd, J=9.3,6.0Hz, 1H), 2.36 (d, J
=27.3Hz, 7H), 1.94-1.83 (m, 1H), 1.74-1.66 (m, 1H), 1.53-1.42 (m, 1H), 1.00 (t, J=7.3Hz,
3H)。
13C NMR(151MHz,CDCl3)δ146.70,139.55,138.22,134.60,130.79,130.60,
129.00,126.63,124.65,118.89,118.55,117.93,116.46,108.27,35.90,28.80,21.79,
20.95,18.41,13.37。
Embodiment 6
- 78 DEG C, N2Under protection, the steamed 2.5mL dichloromethane of weight is added in the reaction tube of 25ml, then by aryl sulfoxid es
139.5mg (0.5mmol) and the nitrile compounds 208mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoroacetic anhydride
158mg (0.75mmol) stirs 12h, and reaction process is tracked with thin-layered chromatography, and it is molten that saturated sodium bicarbonate is added after reaction
Reaction is quenched in liquid (3ml), is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract, organic phase anhydrous sodium sulfate
It is dry, it is concentrated in vacuo, (Rf=0.38, solvent is detached by column chromatography:Petrol ether/ethyl acetate=20/1, v/v), it obtains
The product arrived is colourless oil liquid 103mg, yield 60%.
Target product is characterized as below：
1H NMR(600MHz,CDCl3) δ 8.09 (d, J=8.3Hz, 1H), 7.74 (d, J=7.2Hz, 1H), 7.41-7.36
(m, 1H), 7.36-7.31 (m, 1H), 5.25 (dd, J=8.9,6.5Hz, 1H), 2.36 (s, 3H), 2.34-2.26 (m, 1H),
1.92 (ddt, J=12.9,10.2,6.3Hz, 1H), 1.75 (s, 9H), 1.69-1.63 (m, 1H), 1.54-1.45 (m, 1H),
1.01 (t, J=7.4Hz, 3H).
13C NMR(151MHz,CDCl3)δ149.67,136.97,135.96,129.66,125.67,123.63,
119.60,119.58,116.12,116.07,86.03,29.59,28.30,20.88,18.71,13.57。
Embodiment 7
- 78 DEG C, N2Under protection, the steamed dichloromethane of 2.5mL weights is added in the reaction tube of 25ml, then by aryl sulfoxid es
189mg (0.5mmol) and the nitrile compounds 280mg (0.75mmol) of alpha tin substitution are added, and are eventually adding trifluoroacetic anhydride
158mg (0.75mmol) stirs 10min, is warming up to -60 DEG C, stirs 12h, and reaction process, reaction knot are tracked with thin-layered chromatography
Saturated sodium bicarbonate solution (3ml) is added after beam, reaction is quenched, is to slowly warm up to room temperature, then dichloromethane (3mL × 3) is used to extract
It takes, organic phase is dried with anhydrous sodium sulfate, is concentrated in vacuo, and (Rf=0.18, solvent are detached by column chromatography:Petroleum ether/second
Acetoacetic ester=10/1, v/v), obtained product is white solid 189mg, yield 85%.
Target product is characterized as below：
1H NMR(600MHz,CDCl3) δ 8.57 (s, 1H), 8.30 (dd, J=32.5,8.4Hz, 2H), 7.70 (s, 2H),
7.30 (d, J=8.0Hz, 2H), 5.20 (dd, J=8.7,6.2Hz, 1H), 2.38 (d, J=9.1Hz, 7H), 1.97-1.84 (m,
1H), 1.77-1.64 (m, 1H), 1.55-1.42 (m, 1H), 1.01 (t, J=7.2Hz, 3H).
13C NMR(151MHz,CDCl3)δ146.78,144.92,140.29,139.24,134.44,130.78,
130.59,126.61,121.03,118.69,118.42,115.95,115.92,35.81,28.84,21.72,20.90,
18.48,13.30。
Claims (9)
1. a kind of preparation method of alpha-aromatic nitrile compound, which is characterized in that in the presence of anhydride compound, structural formula (I)
Shown in aryl sulfoxid es with shown in structural formula (II) alpha tin replace nitrile compounds reacted in a solvent, composite structure
Alpha-aromatic nitrile compound shown in formula (III), the general formula of the reaction are as follows：
Wherein, R1Selected from hydrogen, halogen, alkyl, alkoxy, alkyl-carbonyl, cyano or nitro, R2Selected from p-toluenesulfonyl or uncle
Butoxy carbonyl, R3、R4With X independently selected from hydrogen or alkyl, m=3.
2. the preparation method of alpha-aromatic nitrile compound according to claim 1, which is characterized in that structural formula (I)~(III)
In, R1Selected from hydrogen, halogen, C1~C4Alkyl, C1~C4Alkoxy, C1~C4Alkyl-carbonyl or cyano, R2Selected from p-toluenesulfonyl
Or tertbutyloxycarbonyl, R3And R4Independently selected from hydrogen or C1~C4Alkyl, X C1~C4Alkyl, m=3.
3. the preparation method of alpha-aromatic nitrile compound according to claim 1, which is characterized in that the anhydride compound
For trifluoroacetic anhydride, trifluoromethanesulfanhydride anhydride, methanesulfonic acid acid anhydride, p-toluenesulfonic anhydride, Trichloroacetic anhydride, acetic anhydride, a chlorine difluoro second
At least one of acid anhydrides and glutaric anhydride.
4. the preparation method of alpha-aromatic nitrile compound according to claim 1, which is characterized in that anhydride compound and virtue
The molar ratio that adds of base sulfoxide is 1.1~2：1.
5. the preparation method of alpha-aromatic nitrile compound according to claim 4, which is characterized in that anhydride compound and virtue
The molar ratio that adds of base sulfoxide is 1.5：1.
6. the preparation method of alpha-aromatic nitrile compound according to claim 1, which is characterized in that aryl sulfoxid es take with alpha tin
The molar ratio that adds of the nitrile compounds in generation is 1：1.1~2.
7. the preparation method of alpha-aromatic nitrile compound according to claim 6, which is characterized in that aryl sulfoxid es take with alpha tin
The molar ratio that adds of the nitrile compounds in generation is 1：1.5.
8. the preparation method of alpha-aromatic nitrile compound according to claim 1, which is characterized in that the solvent be acetonitrile or
Dichloromethane.
9. the preparation method of alpha-aromatic nitrile compound according to claim 1, which is characterized in that the temperature of the reaction
It it is -80~0 DEG C, the reaction time is 10min~15h.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256314A (en) * | 2019-06-28 | 2019-09-20 | 南京林业大学 | A kind of preparation method and products thereof of beta-aromatic ketone compounds |
| CN112174861A (en) * | 2020-10-04 | 2021-01-05 | 浙江师范大学 | Method and compound for preparing alpha-aryl nitrile |
| WO2022038224A1 (en) | 2020-08-20 | 2022-02-24 | Universitaet Wien | Method for the preparation of aryl or heteroaryl substituted carbonyl or nitrile compounds |
-
2018
- 2018-02-09 CN CN201810136406.0A patent/CN108409628B/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110256314A (en) * | 2019-06-28 | 2019-09-20 | 南京林业大学 | A kind of preparation method and products thereof of beta-aromatic ketone compounds |
| CN110256314B (en) * | 2019-06-28 | 2020-12-15 | 南京林业大学 | Preparation method of beta-aryl ketone compound and product thereof |
| WO2022038224A1 (en) | 2020-08-20 | 2022-02-24 | Universitaet Wien | Method for the preparation of aryl or heteroaryl substituted carbonyl or nitrile compounds |
| CN112174861A (en) * | 2020-10-04 | 2021-01-05 | 浙江师范大学 | Method and compound for preparing alpha-aryl nitrile |
| CN112174861B (en) * | 2020-10-04 | 2022-12-27 | 浙江师范大学 | Method and compound for preparing alpha-aryl nitrile |
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Inventor after: Li Kaixiao Inventor after: Peng Bo Inventor after: Zhao Weizhao Inventor after: Yan Chao Inventor after: Yao Yongna Inventor after: Kang Ting Inventor after: Li Cuanyan Inventor before: Li Kaixiao Inventor before: Zhao Weizhao Inventor before: Yan Chao Inventor before: Yao Yongna Inventor before: Kang Ting Inventor before: Li Cuanyan |
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