CN108409628B - Preparation method of alpha-aryl nitrile compound - Google Patents
Preparation method of alpha-aryl nitrile compound Download PDFInfo
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Abstract
The invention discloses a preparation method of an alpha-aryl nitrile compound, which comprises the following steps: in the presence of an anhydride compound, aryl sulfoxide shown in a structural formula (I) reacts with alpha-tin substituted nitrile compound shown in a structural formula (II) in a solvent to synthesize alpha-aryl nitrile compound shown in a structural formula (III). The method synthesizes the alpha-aryl nitrile compound by aryl sulfoxide and alpha-tin substituted nitrile compound under mild conditions. The method has the advantages of mild reaction conditions, good selectivity, high yield, easy product separation and simple operation.
Description
Technical Field
The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of an alpha-aryl nitrile compound.
Background
Alpha-aryl nitrile compounds are important structural units in many natural products and drugs. The cyano group has good functional group derivation, and thus becomes an important organic synthon. The amide (Inorg. Chim. acta 2005,358,1-21), carboxylic acid (Tetrahedron Lett 2014,55, 3802-.
In addition, α -arylnitrile compounds are also widely present in biological medicine. The medicine containing alpha-aryl nitrile compound structure can be used for treating various diseases. For example, diphenoxylate: a medicament for the treatment of diarrhea; anastrozole: a medicament for the treatment of breast cancer; wumai' an: a medicament for treating coronary heart disease; golopamid: a methoxy derivative of anastrozole, with a 10-fold efficacy as anastrozole; left cabastine: a medicament for treating conjunctivitis; isoflavoprotein: an analgesic and antitussive preparation. Therefore, the synthesis method for preparing the alpha-aryl nitrile compound has important practical significance.
At present, the following methods are mainly reported for synthesizing alpha-aryl nitrile compounds: (I) coupling reaction of aryl halide and cyano compound under strong alkaline condition (tetrahedron.1974,30, 3723) -3735). Although the reaction can successfully synthesize the nitro alpha-aryl nitrile compound, the reaction substrate range is narrow and needs a strong base system to complete; (di), cyanation of benzyl alcohol or benzyl halide (J.org.chem.1999,64,3171-3177) which, although high yield, avoids the use of highly toxic metal cyanide as a cyanide source, has the disadvantage of being able to be carried out at a certain temperature, but limits the application of such reactions. (III) palladium-catalyzed coupling reaction of aryl halide and cyano compound (Angew. chem. int. Ed.2003,42, 5051-5053), which needs to be catalyzed by metallic palladium, so that the condition limits the diversity of the reaction substrate and the application range is limited.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides the preparation method of the alpha-aryl nitrile compound, which has the advantages of mild reaction conditions, good selectivity, high yield, easy product separation, simple operation and the like.
The technical scheme adopted by the invention is as follows:
a method for preparing alpha-aryl nitrile compound, in the presence of acid anhydride compound, aryl sulfoxide shown in structural formula (I) reacts with alpha-tin substituted nitrile compound shown in structural formula (II) in solvent to synthesize alpha-aryl nitrile compound shown in structural formula (III), the general formula of the reaction is as follows:
wherein R is1Selected from hydrogen, halogen, alkyl, alkoxy, alkylcarbonyl, cyano or nitro, R2Selected from p-toluenesulfonyl or tert-butoxycarbonyl, R3、R4And X is independently selected from hydrogen or alkyl, m ═ 3.
Preferably, in the formulae (I) to (III), R1Selected from hydrogen, halogen, C1～C4Alkyl radical, C1～C4Alkoxy radical, C1～C4Alkylcarbonyl or cyano radicals, R2Selected from p-toluenesulfonyl or tert-butoxycarbonyl, R3And R4Independently selected from hydrogen or C1～C4Alkyl, X is C1～C4Alkyl, m ═ 3.
The acid anhydride compound is at least one of trifluoroacetic anhydride, trifluoromethanesulfonic anhydride, methanesulfonic anhydride, p-toluenesulfonic anhydride, trichloroacetic anhydride, acetic anhydride, chlorodifluoroacetic anhydride and glutaric anhydride.
The adding molar ratio of the anhydride compound to the aryl sulfoxide is 1.1-2: 1; preferably, the adding molar ratio of the acid anhydride compound to the aryl sulfoxide is 1.5: 1.
the adding molar ratio of the aryl sulfoxide to the alpha-tin substituted nitrile compound is 1: 1.1-2; preferably, the molar ratio of the aryl sulfoxide to the alpha-tin substituted nitrile compound is 1: 1.5.
the solvent used in the invention is acetonitrile or dichloromethane.
The reaction temperature is-80-0 ℃, and the reaction time is 10 min-15 h.
Compared with the prior art, the method synthesizes the alpha-aryl nitrile compound by the aryl sulfoxide and the alpha-tin substituted nitrile compound under mild conditions, and has the advantages that:
(1) the method has the advantages of mild reaction conditions, good selectivity, high yield, easy product separation and simple operation;
(2) the raw materials used in the method are cheap and easy to obtain, and the defects of over strong alkalinity, strict reaction condition requirements and limited reaction substrates in the traditional method are avoided;
(3) the aryl sulfoxide reacts with the nitrile compound substituted by alpha-tin to prepare the alpha-aryl nitrile compound with stable chemical stability, and a new reaction strategy is provided for the synthesis of the compound.
Detailed Description
Example 1
-78℃，N2Under protection, redistilled 2.5mL of Dichloromethane (DCM) was added to a 25mL reaction tube, 167mg (0.5mmol) of aryl sulfoxide and 280mg (0.75mmol) of α -tin substituted nitrile compound were added, and 158mg (0.75mmol) of trifluoroacetic anhydride (TFAA) was added finally, the reaction was stirred for 12h, followed by thin layer chromatography, after completion of the reaction, saturated sodium bicarbonate solution (3mL) was added to quench the reaction, slowly warmed to room temperature, followed by extraction with dichloromethane (3mL × 3), the organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, and separated by column chromatography (Rf ═ 0.27, developing solvent: petroleum ether/ethyl acetate 10/1, v/v), to give 178mg of product as a white solid in 90% yield.
The mechanism of the reaction involved in this example is as follows:
the target product was characterized as follows:
1H NMR(600MHz,CDCl3)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)145.84,137.02,136.61,135.03,130.56,130.25,126.63,126.22,124.60,119.83,119.25,118.74,115.73,36.04,28.84,21.74,20.97,18.27,13.46。
example 2
-78℃，N2Under protection, redistilled 2.5mL of dichloromethane was added to a 25mL reaction tube, 205.5mg (0.5mmol) of aryl sulfoxide and 280mg (0.75mmol) of α -tin substituted nitrile compound were added, 158mg (0.75mmol) of trifluoroacetic anhydride was added finally, stirring was carried out for 12 hours, the progress of the reaction was followed by thin layer chromatography, after completion of the reaction, a saturated sodium bicarbonate solution (3mL) was added to quench the reaction, the temperature was slowly raised to room temperature, then dichloromethane (3mL × 3) was used for extraction, the organic phase was dried over anhydrous sodium sulfate, vacuum-concentrated, and separated by column chromatography (Rf ═ 0.23, developing solvent: petroleum ether/ethyl acetate ═ 20/1, v/v), and the product was obtained as a white solid 203mg with a yield of 85%.
The target product was characterized as follows:
1H NMR(400MHz,CDCl3)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)146.15,139.87,137.77,134.59,130.29,129.90,127.68,126.58,126.47,119.11,118.52,114.68,114.52,35.87,28.93,21.67,21.27,20.94,13.38。
example 3
-40℃，N2Adding 2.5mL redistilled acetonitrile (MeCN) into a 25mL reaction tube under protection, adding 180.5mg (0.5mmol) of aryl sulfoxide and 280mg (0.75mmol) of alpha-tin substituted nitrile compound, finally adding 158mg (0.75mmol) of trifluoroacetic anhydride, stirring for 12h, tracking the reaction progress by thin layer chromatography, adding saturated sodium bicarbonate solution (3mL) after the reaction is finished, quenching the reaction, slowly heating to room temperature, extracting with dichloromethane (3mL multiplied by 3), drying the organic phase with anhydrous sodium sulfate, vacuum concentrating, passing through a column, concentratingChromatography (Rf 0.23, developing solvent: petroleum ether/ethyl acetate 10/1, v/v) gave 189mg of product as a white solid in 89% yield.
The target product was characterized as follows:
1H NMR(600MHz,CDCl3)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)191.14,146.47,140.82,137.33,134.63,130.55,130.49,129.97,126.66,125.68,124.00,120.96,118.84,116.77,35.90,28.93,21.79,21.05,19.00,13.44。
example 4
-78℃，N2Under protection, redistilled 2.5mL of dichloromethane was added to a 25mL reaction tube, 181.5mg (0.5mmol) of aryl sulfoxide and 280mg (0.75mmol) of α -tin substituted nitrile compound were added, 158mg (0.75mmol) of trifluoroacetic anhydride was added finally, the reaction was stirred for 12 hours, the progress of the reaction was followed by thin layer chromatography, after the end of the reaction, saturated sodium bicarbonate solution (3mL) was added to quench the reaction, the temperature was slowly raised to room temperature, then dichloromethane (3mL × 3) was used for extraction, the organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, and separated by column chromatography (Rf ═ 0.24, developing solvent: petroleum ether/ethyl acetate ═ 10/1, v/v), and the product was obtained as a white solid 206mg with a yield of 96%.
The target product was characterized as follows:
1H NMR(600MHz,CDCl3)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)157.34,145.66,137.65,134.76,131.76,130.90,130.09,126.46,119.17,118.67,116.78,115.17,101.66,55.72,35.93,28.74,21.61,20.84,18.07,13.36。
example 5
-78℃，N2Under protection, redistilled 2.5mL of dichloromethane was added to a 25mL reaction tube, 179mg (0.5mmol) of aryl sulfoxide and 280mg (0.75mmol) of α -tin substituted nitrile compound were added, 158mg (0.75mmol) of trifluoroacetic anhydride was added finally, stirring was carried out for 10min, the temperature was raised to-60 ℃, stirring was carried out for 12h, the progress of the reaction was followed by thin layer chromatography, after completion of the reaction, a saturated sodium bicarbonate solution (3mL) was added to quench the reaction, the temperature was slowly raised to room temperature, then extraction was carried out with dichloromethane (3mL × 3), the organic phase was dried over sodium sulfate, vacuum-concentrated, and separated by column chromatography (Rf ═ 0.28, developing solvent: petroleum ether/ethyl acetate 5/1, v/v), and the product was obtained as a white solid 208mg with a yield of 95%.
The target product was characterized as follows:
1H NMR(600MHz,CDCl3)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)146.70,139.55,138.22,134.60,130.79,130.60,129.00,126.63,124.65,118.89,118.55,117.93,116.46,108.27,35.90,28.80,21.79,20.95,18.41,13.37。
example 6
-78℃，N2Under protection, 2.5mL of redistilled dichloromethane were added to a 25mL reaction tube, and 139.5mg (0) of aryl sulfoxide was added.5mmol) and 208mg (0.75mmol) of the α -tin substituted nitrile compound were added, and finally 158mg (0.75mmol) of trifluoroacetic anhydride was added, and stirred for 12 hours, followed by thin layer chromatography, and after the reaction was completed, a saturated sodium bicarbonate solution (3mL) was added to quench the reaction, slowly warmed to room temperature, and then extracted with dichloromethane (3mL × 3), and the organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, and separated by column chromatography (Rf ═ 0.38, developing solvent: petroleum ether/ethyl acetate ═ 20/1, v/v), to obtain 103mg of the product as a colorless oily liquid, with a yield of 60%.
The target product was characterized as follows:
1H NMR(600MHz,CDCl3)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)149.67,136.97,135.96,129.66,125.67,123.63,119.60,119.58,116.12,116.07,86.03,29.59,28.30,20.88,18.71,13.57。
example 7
-78℃，N2Under protection, 2.5mL of redistilled dichloromethane was added to a 25mL reaction tube, 189mg (0.5mmol) of aryl sulfoxide and 280mg (0.75mmol) of α -tin substituted nitrile compound were added, 158mg (0.75mmol) of trifluoroacetic anhydride was added finally, stirred for 10min, warmed to-60 ℃, stirred for 12h, followed by thin layer chromatography, after the reaction was completed, saturated sodium bicarbonate solution (3mL) was added to quench the reaction, slowly warmed to room temperature, then extracted with dichloromethane (3mL × 3), the organic phase was dried over sodium sulfate, concentrated in vacuo, and separated by column chromatography (Rf ═ 0.18, developing solvent: petroleum ether/ethyl acetate 10/1, v/v), to obtain 189mg of product as a white solid with a yield of 85%.
The target product was characterized as follows:
1H NMR(600MHz,CDCl3)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)146.78,144.92,140.29,139.24,134.44,130.78,130.59,126.61,121.03,118.69,118.42,115.95,115.92,35.81,28.84,21.72,20.90,18.48,13.30。
Claims (8)
1. a method for preparing alpha-aryl nitrile compound is characterized in that aryl sulfoxide shown in structural formula (I) reacts with alpha-tin substituted nitrile compound shown in structural formula (II) in a solvent in the presence of acid anhydride compound to synthesize alpha-aryl nitrile compound shown in structural formula (III), and the general formula of the reaction is as follows:
wherein R is1Selected from hydrogen, halogen, alkyl, alkoxy, alkylcarbonyl, cyano or nitro, R2Selected from p-toluenesulfonyl or tert-butoxycarbonyl, R3Is methyl, R4Is n-Pr, X is n-Bu, and m is 3;
the anhydride compound is trifluoroacetic anhydride.
2. The method for producing an α -arylnitrile compound according to claim 1, wherein R in the structural formulae (I) to (III)1Selected from hydrogen, halogen, C1～C4Alkyl radical, C1～C4Alkoxy radical, C1～C4Alkylcarbonyl or cyano radicals, R2Selected from p-toluenesulfonyl or tert-butoxycarbonyl.
3. The method for producing an α -aryl nitrile compound according to claim 1, wherein the molar ratio of the acid anhydride compound to the aryl sulfoxide is 1.1 to 2: 1.
4. the method for producing an α -aryl nitrile compound according to claim 3, wherein the molar ratio of the acid anhydride compound to the aryl sulfoxide is 1.5: 1.
5. the method for producing an α -aryl nitrile compound according to claim 1, wherein the molar ratio of the aryl sulfoxide to the α -tin-substituted nitrile compound is 1: 1.1 to 2.
6. The method for producing an α -aryl nitrile compound according to claim 5, wherein the molar ratio of the aryl sulfoxide to the α -tin-substituted nitrile compound is 1: 1.5.
7. the method for producing an α -aryl nitrile compound according to claim 1, wherein the solvent is acetonitrile or dichloromethane.
8. The method for producing an α -aryl nitrile compound according to claim 1, wherein the reaction temperature is-80 to 0 ℃ and the reaction time is 10min to 15 hours.
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| Nucleophilic Ortho Allylation of Aryl and Heteroaryl Sulfoxides;Andrew J. Eberhart，等;《ORGANIC LETTERS》;20111014;第13卷(第21期);第5882-5885页 * |
| Redox-Neutral α‑Arylation of Alkyl Nitriles with Aryl Sulfoxides:A Rapid Electrophilic Rearrangement;Li Shang，等;《J. Am. Chem. Soc.》;20170228;第139卷;第4211-4217页 * |
| Sulfoxide-Mediated a-Arylation of Carbonyl Compounds;Xueliang Huang，等;《J. Am. Chem. Soc.》;20110516;第133卷;第8510-8513页 * |
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