CN113861069A - Preparation method of nitrile compound - Google Patents
Preparation method of nitrile compound Download PDFInfo
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- CN113861069A CN113861069A CN202111254803.6A CN202111254803A CN113861069A CN 113861069 A CN113861069 A CN 113861069A CN 202111254803 A CN202111254803 A CN 202111254803A CN 113861069 A CN113861069 A CN 113861069A
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- C07—ORGANIC CHEMISTRY
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- C07C253/00—Preparation of carboxylic acid nitriles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C—CHEMISTRY; METALLURGY
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a nitrile compound, which comprises the following steps of taking an aldoxime derivative as a raw material, adding DPPA and DBU, reacting in an organic solvent, and preparing the nitrile compound in one step, wherein the synthetic route is as follows:
wherein R is aryl, alkyl or alkenyl. The nitrile compound prepared by the invention has the advantages of cheap and easily available raw materials, short synthetic route, simple reaction operation, short reaction time, high yield, easy post-treatment, small environmental pollution, objective economic and practical value and wide application prospect in the field of drug synthesis.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a nitrile compound.
Background
Nitriles are a very important class of organic synthesis intermediates. As an important raw material and an intermediate commonly used in the production of fine chemicals, nitrile compounds have wide application in the fields of medicines, materials, agriculture, chemical industry and the like. In recent years, with the rapid development of science and technology, nitrile compounds are more widely applied in various fields. Therefore, research on the synthesis method of nitrile compounds and development of the diversity of nitrile compounds have become one of the hot issues in the field of organic chemistry.
At present, more nitrile compound synthesis methods are reported, and the nitrile compound synthesis methods mainly include the following steps according to different synthesis raw materials: the method comprises the steps of preparation by a halogenated hydrocarbon cyaniding method, preparation by amine oxidative dehydrogenation, preparation by aromatic alkane C-H or C-C bond breakage, preparation by aromatic alkene C ═ C bond breakage, preparation by aromatic alkyne C ≡ C bond breakage, preparation by aromatic alcohol C-O bond breakage, preparation by aromatic aldehyde ketone and amide C ≡ O bond breakage, preparation by aldoxime C ═ N bond breakage and the like. Among them, the preparation of nitrile compounds by aldoxime C ═ N bond cleavage is an important direction, and the dehydration method is mainly used in the preparation of nitrile C ≡ N from aldoxime C ═ N conversion, and conventional dehydrating agents include strongly acidic (acetic anhydride, trifluoromethanesulfonic anhydride, phthalic anhydride, thionyl chloride, sulfonic acid, etc.), strongly basic (sodium hydroxide, potassium hydroxide, etc.), and metal compounds (pyridinium chlorochromate, scandium trifluoroacetate, etc.), however, the above methods have some limitations such as the use of metal (heavy metal or transition metal) dehydrating agents, harsh reaction conditions (high temperature, anhydrous environment, long reaction time), limited substrate applicability, and the like. Therefore, the search for a new method for synthesizing nitrile compounds is of great significance.
Disclosure of Invention
In order to solve the problems, the invention provides a method for preparing nitrile compounds, which has the advantages of cheap and easily obtained raw materials, short synthetic route, simple reaction operation, high reaction speed, easy post-treatment, high yield, small environmental pollution, suitability for industrial production and objective economic and practical value.
The invention aims to provide a preparation method of nitrile compounds, which takes aldoxime derivatives as raw materials, adds DPPA and DBU, reacts in an organic solvent, and prepares the nitrile compounds in one step, wherein the synthetic route of the nitrile compounds is as follows:
wherein R is aryl, alkyl or alkenyl.
Preferably, the aryl is a benzene aromatic ring, pyridine, imidazole, thiophene, thiazole, pyrimidine or indole.
Preferably, the molar ratio of the diphenyl azide phosphate DPPA, the 1, 8-diazabicycloundec-7-ene DBU and the aldoxime derivative is 1.2:1.1: 1.
Preferably, the organic solvent is one of acetonitrile, dichloromethane and chloroform.
Preferably, the reaction time is 0.5-2 h.
Preferably, the temperature of the reaction is 25-80 ℃.
Preferably, the nitrile compound is prepared by the following steps: adding an organic solvent into a reaction bottle, then sequentially adding an aldoxime derivative and 1, 8-diazabicycloundecen-7-ene DBU, uniformly stirring, slowly adding diphenyl azide phosphate DPPA, reacting at room temperature, carrying out reduced pressure concentration to obtain a nitrile compound crude product, and then carrying out chromatographic separation.
Preferably, thin layer chromatography is used to detect the completion of the reaction, and the reaction is stopped after completion.
Preferably, the eluent for chromatographic separation is petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 2-10: 1.
Compared with the prior art, the invention has the following beneficial effects:
the process has the advantages of cheap and easily obtained raw materials, short synthetic route, simple reaction operation, short reaction time, high yield, easy post-treatment, small environmental pollution, objective economic and practical value and wide application prospect in the field of drug synthesis.
Drawings
FIG. 1 is a diagram of the synthesis scheme for the preparation of nitrile compounds according to the present invention;
FIG. 2 shows the preparation of 2-nitrobenzonitrile compound prepared in example 2 of the present invention1H-NMR chart;
FIG. 3 is a diagram of the preparation of 4-bromoxynil compound of example 3 of the present invention1H-NMR chart;
FIG. 4 shows a process for preparing a methyl 4-cyanobenzoate compound of example 4 of the present invention1H-NMR chart;
FIG. 5 is a diagram of 4-propoxybenzonitrile compound prepared in example 5 of the present invention1H-NMR chart;
FIG. 6 shows a preparation of 4-butoxybenzonitrile compound prepared in example 6 of the present invention1H-NMR chart;
FIG. 7 is a diagram showing a process for preparing a 4-benzyloxybenzonitrile compound prepared in example 7 of the present invention1H-NMR chart;
FIG. 8 is a drawing showing the preparation of 2, 2-dimethoxybenzonitrile compound prepared in example 8 of the present invention1H-NMR chart;
FIG. 9 is a drawing showing the preparation of a 2-cyanopyridine compound of example 9 of the present invention1H-NMR chart;
FIG. 10 is a drawing showing a preparation method of (E) -cinnamonitrile compound prepared in example 10 of the present invention1H-NMR chart;
FIG. 11 is a drawing showing a method for preparing (E) -4-chlorocinnamonitrile compound according to example 11 of the present invention1H-NMR chart;
FIG. 12 is a photograph of (E) -2-benzylidene heptanitrile compound prepared according to example 12 of the present invention1H-NMR chart;
FIG. 13 is a photograph of (E) -3- (furan-2-yl) acrylonitrile compound prepared in example 13 of the present invention1H-NMR chart;
FIG. 14 is a single crystal structural view of a (E) -3- (furan-2-yl) acrylonitrile compound prepared in example 13 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It is to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the scope of the present invention, and that the various materials, reagents, equipment and equipment used in the following examples of the present invention may be commercially available or may be prepared by conventional methods, unless otherwise specified, wherein DPPA is diphenyl azidophosphate and DBU is 1, 8-diazabicycloundec-7-ene.
Example 1
A preparation method of nitrile compounds comprises the steps of taking aldoxime derivatives as raw materials, adding DPPA and DBU, reacting in an organic solvent, and preparing the nitrile compounds in one step, wherein the synthetic route is as follows:
wherein R is aryl, alkyl, alkenyl, pyridine. The synthesis scheme of the nitrile compound is shown in figure 1, and the possible reaction mechanism is as follows:
EXAMPLE 22 Synthesis of Nitrobenzonitrile
Adding 498mg (3.0mmol) of 2-nitrobenzaldehyde oxime and 548mg (3.6mmol) of DBU into a reaction bottle of acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) of DPPA, reacting at room temperature of 25 ℃ for 30min, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a tan solid in 68.5% yield.1H NMR(400MHz,DMSO-d6) δ 8.39(d, J ═ 8.8Hz,2H),8.19(d, J ═ 8.8Hz, 2H). See in particular fig. 2.
EXAMPLE 34 Synthesis of bromoxynil
597mg (3.0mmol) of 4-bromobenzaldehyde oxime and 548mg (3.6mmol) of DBU are added into a reaction bottle of acetonitrile (4mL), the mixture is stirred uniformly, 908mg (3.3mmol) of DPPA is slowly added, the mixture reacts for 1h at the room temperature of 25 ℃, after the TLC monitoring reaction is finished, the mixture is concentrated under reduced pressure, and the obtained crude product is separated by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a white solid in 71.0% yield.1H NMR(400MHz,CDCl3) δ 7.66(d, J ═ 7.6Hz,2H),7.55(d, J ═ 7.6Hz, 2H). See in particular fig. 3.
EXAMPLE 44 Synthesis of methyl cyanobenzoate
537mg (3.0mmol) of methyl 4- (hydroxyimino) methylbenzoate and 548mg (3.6mmol) of DBU are added into a reaction bottle of acetonitrile (4mL), after uniform stirring, 908mg (3.3mmol) of DPPA is slowly added, the mixture reacts for 2 hours at the room temperature of 25 ℃, after TLC monitoring reaction is finished, the mixture is concentrated under reduced pressure, and the obtained crude product is separated by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a pale yellow solid in 66.2% yield.1H NMR(400MHz,CDCl3) δ 8.16(d, J ═ 7.5Hz,2H),7.77(d, J ═ 7.5Hz,2H),3.98(s, 3H). See in particular fig. 4.
EXAMPLE 54 Synthesis of propoxybenzonitrile
537mg (3.0mmol) of 4-propoxybenzaldehyde oxime and 548mg (3.6mmol) of DBU are added into a reaction bottle of chloroform (4mL) and are stirred uniformly, 908mg (3.3mmol) of DPPA is slowly added, the mixture reacts for 30min at the room temperature of 25 ℃, after the TLC monitoring reaction is finished, the mixture is concentrated under reduced pressure, and the obtained crude product is separated by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a pale yellow liquid in 80.7% yield.1H NMR(400MHz,DMSO-d6) δ:7.75(dd, J ═ 9.2,2.2Hz,2H),7.12-7.06(m,2H),4.01(t, J ═ 6.5Hz,2H),1.78-1.66(m,2H),0.97(t, J ═ 7.4Hz, 3H). See in particular fig. 5.
EXAMPLE 64 Synthesis of butoxybenzonitrile
Adding 579mg (3.0mmol) of 4-butoxybenzaldehyde oxime and 548mg (3.6mmol) of DBU into a reaction bottle of dichloromethane (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) of DPPA, reacting at room temperature of 25 ℃ for 45min, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a pale yellow liquid in 78.3% yield.1H NMR(400MHz,DMSO-d6) δ:7.81-7.68(m,2H),7.76-7.70(m,2H),7.14-7.02(m,2H),7.10-7.04(m,2H),4.03(t, J ═ 6.5Hz,2H),1.69(dt, J ═ 14.4,6.5Hz,2H),1.47-1.34(m,2H),0.91(t, J ═ 7.4Hz, 3H). See in particular fig. 6.
Example Synthesis of 74-benzyloxybenzonitrile
681mg (3.0mmol) of 4-benzyloxybenzaldehyde oxime, 548mgAdding (3.6mmol) DBU into acetonitrile (4mL) reaction flask, stirring, slowly adding 908mg (3.3mmol) DPPA, reacting at 50 deg.C for 30min, monitoring by TLC, concentrating under reduced pressure, separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a white solid in 82.2% yield.1H NMR(400MHz,DMSO-d6) δ 7.83-7.75(m,2H),7.49-7.44(m,2H),7.44-7.38(m,2H),7.37(dd, J ═ 6.4,2.0Hz,1H),7.23-7.15(m,2H),5.21(s, 2H). See in particular fig. 7.
EXAMPLE 82 Synthesis of 2, 2-Dimethoxybenzonitrile
Adding 543mg (3.0mmol) of 2, 4-dimethoxybenzaldehyde oxime and 548mg (3.6mmol) of DBU into a reaction bottle of acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) of DPPA, reacting at room temperature of 25 ℃ for 30min, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a pale yellow liquid in 81.4% yield. 1H NMR (400MHz, DMSO-d)6) δ 7.50(d, J ═ 8.4Hz,1H),6.54(d, J ═ 8.5Hz,1H),6.48(s,1H),3.93(s,3H),3.88(s, 3H). See in particular fig. 8.
EXAMPLE 92 Synthesis of cyanopyridine
Adding 366mg (3.0mmol) pyridine-2-formaldehyde oxime and 548mg (3.6mmol) DBU into a reaction bottle of acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) DPPA, reacting at 80 deg.C for 1.5min, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetateNo. 5:1) gave a red-brown liquid in 64.2% yield.1H NMR(400MHz,DMSO-d6) Delta 4.87(s,2H),4.54(s,2H),4.38(s, 5H). See in particular fig. 9.
Example 10 Synthesis of (E) -Cinnanitrile
Adding 441mg (3.0mmol) of cinnamaldehyde oxime and 548mg (3.6mmol) of DBU into a reaction bottle of acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) of DPPA, reacting at 50 ℃ for 1h, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a pale yellow liquid in 66.4% yield.1H NMR(400MHz,DMSO-d6) δ 7.7-7.62(m,3H),7.50-7.41(m,3H),6.49(d, J ═ 16.8Hz, 1H). See in particular fig. 10.
Example 11 Synthesis of (E) -4-chlorocinnamonitrile
Adding 543mg (3.0mmol) of 4-chlorocinnamaldehyde oxime and 548mg (3.6mmol) of DBU into a reaction bottle of acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) of DPPA, reacting at 60 ℃ for 1.5h, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetate10:1) gave a pale yellow liquid in 62.8% yield.1H NMR(400MHz,DMSO-d6) δ 7.40(s,1H),7.29(t, J ═ 3.8Hz,4H),5.89(d, J ═ 16.7Hz, 1H). See in particular fig. 11.
EXAMPLE 12 Synthesis of (E) -2-benzylidene heptanitrile
Adding 651mg (3.0mmol) alpha-amyl cinnamaldehyde oxime and 548mg (3.6mmol) DBU into acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) DPPA, reacting at 50 ℃ for 1.5h, monitoring by TLC, concentrating under reduced pressure, and purifying the obtained crude product by column chromatographyChromatographic separation (eluent V)Petroleum ether:VEthyl acetateNo. 5:1) gave a colorless liquid in 58.4% yield.1H NMR(400MHz,DMSO-d6) δ 7.49-7.38(m,6H),2.46(t, J ═ 7.7Hz,2H),1.61-1.52(m,2H),1.31-1.24(m,4H),0.84(t, J ═ 6.8Hz, 3H). See in particular fig. 12.
Example 13 Synthesis of (E) -3- (furan-2-yl) acrylonitrile
Adding 411mg (3.0mmol) of 3- (2-furyl) acraldehyde oxime and 548mg (3.6mmol) of DBU into acetonitrile (4mL), stirring uniformly, slowly adding 908mg (3.3mmol) of DPPA, reacting at 50 ℃ for 2h, after TLC monitoring reaction, concentrating under reduced pressure, and separating the obtained crude product by column chromatography (eluent V)Petroleum ether:VEthyl acetateNo. 5:1) gave a tan solid in 63.6% yield.1HNMR(400MHz,CDCl3) δ 7.52(s,1H),7.14(d, J ═ 16.3Hz,1H),6.65(s,1H),6.53(s,1H),5.79(d, J ═ 16.2Hz, 1H). See in particular fig. 13.
Dissolving (E) -3- (furan-2-yl) acrylonitrile in a mixed solvent of dichloromethane and methanol, naturally volatilizing at room temperature to obtain colorless crystals after about 5 days, and selecting the thickness of 0.15 multiplied by 0.12 multiplied by 0.08mm3Collecting data by an APEXII CCD type X-ray single crystal diffractometer, and adopting MoK alpha rays monochromatized by graphite
Diffraction points were collected by omega-2 theta scanning and the data were processed using the SHELXL-97 program to solve directly the crystal structure.
The crystal structure of the product (E) -3- (furan-2-yl) acrylonitrile (1q) belongs to the monoclinic system, as shown in Table 1, P21N space group, cell parameters
ɑ＝γ＝90.00°，β＝102.59(4)°，
Z＝4，T＝170.0K，Dc＝1.314g/cm3，μ＝0.09mm-1And F (000) ═ 248. The three-dimensional structure of the product 1q can be seen by X-ray single crystal diffraction, and particularly, the three-dimensional structure is shown in an attached figure 14.
TABLE 1 Crystal data and Structure refinement of the product (E) -3- (furan-2-yl) acrylonitrile (1q)
It should be noted that, when the present invention relates to a numerical range, it should be understood that two endpoints of each numerical range and any value between the two endpoints can be selected, and since the steps and methods adopted are the same as those in the embodiment, in order to prevent redundancy, the present invention describes a preferred embodiment. While preferred embodiments of the present invention have been described, additional variations and modifications in those embodiments may occur to those skilled in the art once they learn of the basic inventive concepts. Therefore, it is intended that the appended claims be interpreted as including preferred embodiments and all such alterations and modifications as fall within the scope of the invention.
It will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (9)
1. A preparation method of nitrile compounds is characterized in that aldoxime derivatives are taken as raw materials, DPPA and DBU are added, and the nitrile compounds are obtained through one-step reaction in an organic solvent, wherein the synthesis route is as follows:
wherein R is aryl, alkyl or alkenyl.
2. The method for producing a nitrile compound according to claim 1, wherein the aryl group is a benzene-aryl ring, pyridine, imidazole, thiophene, thiazole, pyrimidine, or indole.
3. The method for producing a nitrile compound according to claim 1, wherein the molar ratio of DPPA, DBU and aldoxime derivative is 1.2:1.1: 1.
4. The method for producing a nitrile compound according to claim 1, wherein the organic solvent is one of acetonitrile, dichloromethane, and chloroform.
5. The method for producing a nitrile compound according to claim 1, wherein the reaction time is 0.5 to 2 hours.
6. The method for producing a nitrile compound according to claim 1, wherein the reaction temperature is 25 to 80 ℃.
7. The method for producing a nitrile compound according to claim 1, characterized in that the nitrile compound is produced by the steps of: adding an organic solvent into a reaction bottle, then sequentially adding an aldoxime derivative and DBU, stirring uniformly, slowly adding DPPA, reacting at room temperature, carrying out reduced pressure concentration to obtain a nitrile compound crude product, and then carrying out chromatographic separation.
8. The method according to claim 7, wherein the completion of the reaction is detected by thin layer chromatography, and the reaction is stopped after completion of the reaction.
9. The method for producing a nitrile compound according to claim 7, wherein the eluent for the chromatographic separation is petroleum ether and ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate is 2-10: 1.
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| CN114437868A (en) * | 2022-02-28 | 2022-05-06 | 东莞波顿香料有限公司 | Jasmine-like compound and gardenia-like incense |
| CN114437868B (en) * | 2022-02-28 | 2024-01-12 | 东莞波顿香料有限公司 | Jasmine fragrance compound and gardenia fragrance type fragrance |
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