CN115043755B - Preparation method of alpha, beta-unsaturated imine compound - Google Patents
Preparation method of alpha, beta-unsaturated imine compound Download PDFInfo
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- CN115043755B CN115043755B CN202210870541.4A CN202210870541A CN115043755B CN 115043755 B CN115043755 B CN 115043755B CN 202210870541 A CN202210870541 A CN 202210870541A CN 115043755 B CN115043755 B CN 115043755B
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Abstract
The invention belongs to the technical field of fine chemicals and related chemistry, and provides a preparation method of an alpha, beta-unsaturated imine compound, which takes aryl sulfoxide and allyl nitrile as raw materials, and reacts for 18 hours at minus 55 ℃ in the presence of an activating agent under the condition of an anhydrous organic solvent, reacts for 0.5 hour at minus 95 ℃ in the presence of alkali, and reacts for 12 hours at minus 70 ℃ in the presence of arylamine to obtain the corresponding alpha, beta-unsaturated imine compound. The synthesis method has the beneficial effects that the reaction condition is mild, the functional group compatibility is good, and the product stability is good; the alpha, beta-unsaturated imine compound synthesized by the method can be further functionalized to obtain various compounds, and is applied to the development and research of natural products, functional materials and fine chemicals.
Description
Technical Field
The invention belongs to the technical field of fine chemicals and related chemistry, and provides a preparation method of a polysubstituted unsaturated imine compound.
Background
Imine is a very important organic compound widely present in nature in many natural products having biological activity, and furthermore, imine is an important functional group, and various compounds such as various amines, amino acids, and polypeptides can be easily obtained by various transformations. Among them, α, β -unsaturated imines are very specific compounds in imine compounds, and because a group of conjugated carbon-carbon double bonds and carbon-nitrogen double bonds exist in the molecule, the compounds usually have multiple reaction sites, and different transformations of the compounds have attracted attention of numerous chemists. The alpha, beta-unsaturated imine can be used as electrophilic reagent to generate Michael type 1,4 or 1,2-addition reaction, as diene body to generate [4+2] Diels-Alder cyclization reaction or generate [3+2] cycloaddition reaction with 1,3-dipole compound, and can also generate oxidation, reduction, hydrolysis and other reactions.
Generally, imine compounds have poor stability and are often difficult to separate to obtain pure products, so that development of a new method for preparing stable alpha, beta-unsaturated imine compounds has become a key point of attention of chemical researchers. Therefore, research and development of an efficient method for preparing the stable alpha, beta-unsaturated imine compound have important practical significance for providing more abundant intermediates for the synthesis of drug molecules. At present, a synthesis method for directly and efficiently obtaining a stable alpha, beta-unsaturated imine compound by a one-pot multi-component series reaction starting from aryl sulfoxide has not been reported.
Disclosure of Invention
The invention provides a novel preparation method of alpha, beta-unsaturated imine compound, and the synthesis method has mild reaction conditions, good functional group compatibility and good product stability.
The technical scheme of the invention is as follows:
a high-efficiency preparation method of alpha, beta-unsaturated imine compound is characterized in that aryl sulfoxide and allyl nitrile are used as raw materials, and react for 18 hours at-55 ℃ in the presence of an activating agent and in the presence of an anhydrous organic solvent, react for 0.5 hour at-95 ℃ in the presence of alkali and react for 12 hours at-70 ℃ in the presence of aromatic amine to obtain the corresponding alpha, beta-unsaturated imine compound, and the synthetic route is as follows:
R 1 selected from hydrogen, alkyl, halogen;
R 2 selected from hydrogen, alkyl, halogen, alkoxy;
R 2 in ortho, meta or ortho position with respect to the aromatic amineAligning;
the molar ratio of the aryl sulfoxide to the allyl nitrile is 1:1-1:3;
the molar ratio of the aryl sulfoxide to the activating agent is 1:1-1.5;
the molar ratio of the aryl sulfoxide to the alkali is 1:2-1:3;
the molar ratio of the aryl sulfoxide to the arylamine is 1:1-1:2;
the molar concentration of the aryl sulfoxide in the system was 0.17mmol/mL.
The anhydrous organic solvent is one or more of diethyl ether, methyl tert-butyl ether, 1,4-dioxane, methyl cyclopentyl ether, dichloromethane, tetrahydrofuran and 1,2-dichloroethane, preferably tetrahydrofuran and dichloromethane.
The activating agent is one or a mixture of more than two of trifluoromethanesulfonic anhydride, p-toluenesulfonic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride and methanesulfonic anhydride, and is preferably trifluoromethanesulfonic anhydride.
The alkali is 1,8-diazohetero-spiro [5.4.0] undec-7-ene, triethylene diamine, N-ethyl morpholine, N '-diisopropyl ethylamine or a mixture of more than two of triethylamine, preferably N, N' -diisopropyl ethylamine or N-ethyl morpholine.
The separation method comprises recrystallization, column chromatography and the like.
The solvent used in the recrystallization method comprises petroleum ether, ethyl acetate, diethyl ether, acetone, chloroform, n-hexane and dichloromethane.
When the product is separated by column chromatography, silica gel or neutral alumina can be used as stationary phase, and the developing agent is generally polar and nonpolar mixed solvent, such as ethyl acetate-petroleum ether, ethyl acetate-n-hexane, dichloromethane-petroleum ether, and methanol-petroleum ether.
The synthesis method has the beneficial effects that the reaction condition is mild, the functional group compatibility is good, and the product stability is good; the alpha, beta-unsaturated imine compound synthesized by the method can be further functionalized to obtain various compounds, and is applied to the development and research of natural products, functional materials and fine chemicals.
Drawings
FIG. 1 is a schematic view of an α, β -unsaturated imine compound 2a in example 1 1 H nuclear magnetic spectrum.
FIG. 2 is a schematic view of an α, β -unsaturated imine compound 2a in example 1 13 C nuclear magnetic spectrum.
FIG. 3 is a schematic view of an α, β -unsaturated imine compound 2b in example 2 1 H nuclear magnetic spectrum.
FIG. 4 is a schematic view of an α, β -unsaturated imine compound 2b in example 2 13 C nuclear magnetic spectrum.
FIG. 5 is a schematic view of an α, β -unsaturated imine compound 2c in example 3 1 H nuclear magnetic spectrum.
FIG. 6 is a schematic view of preparation of an α, β -unsaturated imine compound 2c in example 3 13 C nuclear magnetic spectrum.
FIG. 7 is a schematic view of preparation of an α, β -unsaturated imine compound 2d in example 4 1 H nuclear magnetic spectrum.
FIG. 8 is a schematic view of an α, β -unsaturated imine compound 2d in example 4 13 C nuclear magnetic spectrum.
FIG. 9 is a drawing showing a preparation of an α, β -unsaturated imine compound 2e in example 5 1 H nuclear magnetic spectrum.
FIG. 10 is a drawing showing a preparation of an α, β -unsaturated imine compound 2e in example 5 13 C nuclear magnetic spectrum.
FIG. 11 is a schematic view showing that the α, β -unsaturated imine compound 2f in example 6 1 H nuclear magnetic spectrum.
FIG. 12 is a drawing showing a preparation of an α, β -unsaturated imine compound 2f in example 6 13 C nuclear magnetic spectrum.
FIG. 13 is a drawing showing 2g of an α, β -unsaturated imine compound in example 7 1 H nuclear magnetic spectrum.
FIG. 14 is a drawing showing 2g of an α, β -unsaturated imine compound in example 7 13 C nuclear magnetic spectrum.
Detailed Description
The preparation method of the polysubstituted alpha, beta-unsaturated imine compound has the advantages of mild reaction conditions, good functional group compatibility, good product stability and the like.
The invention will be further illustrated with reference to the following specific examples. These examples are intended to illustrate the invention and are not intended to limit the scope of the invention. The simple replacement or improvement of the present invention by those skilled in the art is within the technical scheme of the present invention.
Example 1: synthesis of alpha, beta-unsaturated imine Compound 2a
In a dry 25mL reactor, aryl sulfoxide (1a, 0.120g,0.5 mmol) represented by the above formula, allyl nitrile (0.121mL, 1.5 mmol) and anhydrous dichloromethane (3.0 mL) were sequentially added, trifluoromethanesulfonic anhydride (0.127mL, 0.75mmol) was added at 55 ℃, and the mixture was stirred for 18 hours. N-ethylmorpholine (0.157mL, 1.25mmol) was added to the mixture at-95 ℃ and after stirring for 0.5h, 4-methylaniline (0.107g, 1.0 mmol) was added and the mixture was warmed to-70 ℃ and stirred for 12h. Column chromatography (silica gel, 200-300 mesh; developing solvent, ethyl acetate-petroleum ether) gave 2a as a yellow oily liquid product, 0.110g, 72% yield.
1 H NMR(600MHz,CDCl 3 ):δ7.13(d,J＝7.9Hz,2H),6.72(d,J＝8.0Hz,2H),6.65–6.60(m,1H),6.53–6.43(m,3H),6.37–6.31(m,1H),5.40(d,J＝16.2Hz,1H),3.75(s,3H),2.83–2.71(m,2H),2.33(s,3H). 13 C NMR(151MHz,CDCl 3 ):δ170.9,155.5,148.6,147.3,138.6,136.7,133.9,132.3,129.6,122.4,120.4,116.6,104.1,53.4,51.2,42.0,21.0.
Example 2: synthesis of alpha, beta-unsaturated imine Compound 2b
The same procedure as in example 1 was repeated, except that aniline (0.093g, 1.0 mmol) was used to obtain the corresponding α, β -unsaturated imine compound 2b,0.098g, as a yellow oily liquid, in a yield of 67%.
1 H NMR(600MHz,CDCl 3 ):δ7.34–7.30(m,2H),7.12–7.08(m,1H),6.81(d,J＝8.1Hz,2H),6.63(dd,J＝10.1,1.5Hz,1H),6.52–6.44(m,3H),6.36(dd,J＝10.4,2.5Hz,1H),5.40(d,J＝16.3Hz,1H),3.75(s,3H),2.81–2.72(m,2H). 13 C NMR(151MHz,CDCl 3 ):δ170.8,155.5,149.8,148.5,139.0,137.1,132.1,129.0,124.3,122.3,120.3,116.6,104.2,53.4,51.2,41.9.
Example 3: synthesis of alpha, beta-unsaturated imine Compound 2c
The same procedure as in example 1 was repeated, except that 3-bromoaniline (0.172g, 1.0 mmol) was used to obtain the corresponding α, β -unsaturated imine compound 2c,0.115g, as a colorless oily liquid in 62% yield.
1 H NMR(600MHz,CDCl 3 ):δ7.23(d,J＝8.0Hz,1H),7.21–7.17(m,1H),6.99–6.95(m,1H),6.74(d,J＝7.7Hz,1H),6.61(d,J＝10.3Hz,1H),6.53–6.45(m,2H),6.42(s,2H),5.41(d,J＝16.2Hz,1H),3.76(s,3H),2.82–2.73(m,2H). 13 C NMR(151MHz,CDCl 3 ):δ170.7,156.1,151.4,148.3,139.9,137.8,131.8,130.5,127.1,123.1,122.8,122.1,119.1,116.6,104.4,53.5,51.3,42.0.
Example 4: synthesis of alpha, beta-unsaturated imine Compound 2d
In a dry 25mL reactor, aryl sulfoxide (1a, 0.120g,0.5 mmol) represented by the above formula, allyl nitrile (0.121mL, 1.5 mmol) and anhydrous dichloromethane (3.0 mL) were sequentially added, trifluoromethanesulfonic anhydride (0.127mL, 0.75mmol) was added at 55 ℃, and the mixture was stirred for 18 hours. N, N' -diisopropylethylamine (0.218mL, 1.25mmol) was added to the mixture at-95 ℃ and stirred for 0.5h, then 4-methoxyaniline (0.123g, 1.0 mmol) was added, and then the mixture was warmed to-70 ℃ and stirred for 12h. Column chromatography (silica gel, 200-300 mesh; developing solvent, ethyl acetate-petroleum ether) gave 2d as a yellow oily liquid product, 0.119g, in 74% yield.
1 H NMR(600MHz,CDCl 3 ):δ6.89–6.85(m,2H),6.82–6.76(m,2H),6.62(dd,J＝10.1,1.7Hz,1H),6.56(dd,J＝10.4,1.8Hz,1H),6.52–6.42(m,2H),6.35(dd,J＝10.4,2.6Hz,1H),5.40(d,J＝16.2Hz,1H),3.79(s,3H),3.75(s,3H),2.80–2.72(m,2H). 13 C NMR(151MHz,CDCl 3 ):δ170.9,156.9,155.6,148.6,142.7,138.7,136.7,132.2,122.3,121.9,116.6,114.3,104.1,55.6,53.4,51.3,42.0.
Example 5: synthesis of alpha, beta-unsaturated imine Compound 2e
The same operation as in example 4 was conducted, and from 2-naphthylamine (0.143g, 1.0 mmol), the corresponding α, β -unsaturated imine compound 2e,0.122g, was obtained as a yellow solid in a yield of 71%.
1 H NMR(600MHz,CDCl 3 ):δ7.85–7.79(m,2H),7.77(d,J＝8.1Hz,1H),7.49–7.44(m,1H),7.43–7.38(m,1H),7.18(s,1H),7.06(d,J＝8.5Hz,1H),6.69(d,J＝10.1Hz,1H),6.55–6.46(m,3H),6.36(d,J＝10.3Hz,1H),5.41(d,J＝16.2Hz,1H),3.77(s,3H),2.84–2.72(m,2H). 13 C NMR(151MHz,CDCl 3 ):δ170.8,155.8,148.5,147.6,139.1,137.2,133.9,132.1,130.9,129.0,127.8,127.5,126.6,124.9,122.3,121.4,116.6,116.2,104.2,53.4,51.3,41.9.
Example 6: synthesis of alpha, beta-unsaturated imine Compound 2f
In a dry 25mL reactor, aryl sulfoxide (1b, 0.127g,0.5 mmol) represented by the above formula, allyl nitrile (0.121mL, 1.5 mmol) and anhydrous tetrahydrofuran (3.0 mL) were sequentially added, trifluoromethanesulfonic anhydride (0.127mL, 0.75mmol) was added at 55 ℃, and the mixture was stirred for 18 hours. N-ethylmorpholine (0.157mL, 1.25mmol) was added to the mixture at-95 ℃ and after stirring for 0.5h, aniline (0.093g, 1.0 mmol) was added and the mixture was stirred for 12h at-70 ℃. Column chromatography (silica gel, 200-300 mesh; developing solvent, ethyl acetate-petroleum ether) gave 2f,0.095g, 62% yield as a colorless liquid product.
1 H NMR(600MHz,CDCl 3 ):δ7.35–7.30(m,2H),7.11–7.06(m,1H),6.82–6.73(m,2H),6.53–6.45(m,1H),6.42(d,J＝10.8Hz,1H),6.35–6.28(m,2H),5.43–5.35(m,1H),3.75(s,3H),2.82–2.71(m,2H),2.14–2.07(m,3H). 13 C NMR(151MHz,CDCl 3 ):δ171.4,156.2,150.6,149.1,138.2,137.7,133.5,129.0,123.8,122.4,120.1,116.8,103.9,53.3,51.0,42.1,18.4.
Example 7: synthesis of 2g of an α, β -unsaturated imine Compound
The same procedure as in example 6 was repeated, using aryl sulfoxide (1c, 0.137g,0.5 mmol) represented by the above formula, to obtain 2g (E/Z = 55/45), 0.096g, yellow oil, 59% yield of the corresponding α, β -unsaturated imine compound.
1 H NMR(600MHz,CDCl 3 ):δ7.41–7.31(m,2H),7.18–7.10(m,1H),6.90–6.77(m,2.45H),6.70–6.64(m,1.1H),6.52(d,J＝9.9Hz,0.45H),6.46–6.35(m,1H),6.28(d,J＝9.8Hz,0.55H),6.13(d,J＝10.0Hz,0.45H),5.47(d,J＝16.2Hz,1H),3.78(s,3H),3.20–3.05(m,1H),3.02–2.88(m,1H). 13 C NMR(151MHz,CDCl 3 ):δ168.83,168.81,155.7,155.1,149.6,149.4,147.9,145.3,141.7,137.7,136.0,132.5,132.3,129.3,129.1,124.8,124.7,122.9,122.3,120.28,120.25,116.7,104.5,57.0,56.8,53.9,38.7,38.6.
Application example 1:
in a 25mL reactor, the compound 2a (0.153g, 0.5 mmol) represented by the above formula and Et were added in this order 2 O (2 mL), naOH (10% aq.,2 mL), and stirred at room temperature for 12h. Extraction with ethyl acetate and concentration in vacuo, meOH (10 mL) was added to the resulting concentrate column, followed by continuous passage of O into the reaction mixture at-78 deg.C 3 After reacting for 1h, naBH is added 4 (0.046 g, 5mmol) and gradual recoveryAnd returning to room temperature. With saturated NH 4 The reaction was quenched with aqueous Cl, extracted with DCM and concentrated in vacuo. Column chromatography (silica gel, 200-300 mesh; developing solvent, ethyl acetate-petroleum ether) was performed to obtain the colorless oily liquid compound 3a,0.077g, in a yield of 68%.
The compound 3a obtained in application example 1 is a known important intermediate (j.am. Chem. Soc.2007,129, 3490-3491), and can be used for synthesis of various intermediates or drugs.
Claims (2)
1. A method for preparing alpha, beta-unsaturated imine compound is characterized in that aryl sulfoxide and allyl nitrile are used as raw materials, and the raw materials are reacted for 18 hours at minus 55 ℃ under the condition of anhydrous organic solvent in the presence of activating agent; reacting at-95 ℃ for 0.5 hour in the presence of a base; in the presence of arylamine, reacting at-70 deg.C for 12 hr to obtain corresponding alpha, beta-unsaturated imine compound, the synthetic route is as follows:
R 1 selected from hydrogen, alkyl, halogen;
R 2 selected from hydrogen, alkyl, halogen, alkoxy;
R 2 at ortho, meta or para position of the arylamine;
the molar ratio of the aryl sulfoxide to the allyl nitrile is 1:1-1:3;
the molar ratio of the aryl sulfoxide to the activating agent is 1:1-1;
the molar ratio of the aryl sulfoxide to the alkali is 1:2-1:3;
the molar ratio of the aryl sulfoxide to the arylamine is 1:1-1:2;
the molar concentration of the aryl sulfoxide in the system is 0.17mmol/mL;
the activating agent is one or a mixture of more than two of trifluoromethanesulfonic anhydride, p-toluenesulfonic anhydride, trichloroacetic anhydride, trifluoroacetic anhydride and methanesulfonic anhydride;
the alkali is one or more of 1,8-diazohetero-double spiro [5.4.0] undec-7-ene, triethylene diamine, N-ethyl morpholine, N' -diisopropylethylamine and triethylamine.
2. The production method according to claim 1, the anhydrous organic solvent is one or more of diethyl ether, methyl tert-butyl ether, 1,4-dioxane, methyl cyclopentyl ether, dichloromethane, tetrahydrofuran and 1,2-dichloroethane.
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