CN118271227A - Method for synthesizing 4-formylpyrrole derivative by silver catalysis and application - Google Patents

Method for synthesizing 4-formylpyrrole derivative by silver catalysis and application Download PDF

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CN118271227A
CN118271227A CN202410349988.6A CN202410349988A CN118271227A CN 118271227 A CN118271227 A CN 118271227A CN 202410349988 A CN202410349988 A CN 202410349988A CN 118271227 A CN118271227 A CN 118271227A
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formylpyrrole
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reaction
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刘建全
顾一笑
王香善
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Jiangsu Normal University
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Abstract

A method for synthesizing 4-formylpyrrole derivatives by silver catalysis and application thereof specifically comprises the following steps: adding alkenyl nitrone compounds of the formula 1 and isocyanoacetate of the formula 2 serving as reaction raw materials into an organic solvent, adding alkali, adding argon for protection under the catalysis of metallic silver salt, stirring at 80 ℃ for reaction, and performing TLC tracking reaction until the reaction is complete, thereby preparing the 4-formylpyrrole derivatives of the formula 3 after the treatment of reaction liquid; the molar ratio between the alkenyl nitrone compound and the isocyanoacetate is 1:1, a step of; the molar ratio between the metallic silver salt and the alkenyl nitrone compound is 1:5. the invention is synthesized by a one-pot method of cycloaddition reaction, has simple operation, easily obtained reagent, mild reaction condition, environment-friendly reaction system, easy separation and purification of products and high yield, and is suitable for synthesizing various highly functionalized 4-formylpyrrole derivatives; the application proves that the 4-formylpyrrole compound can be converted into the N-sulfonylated pyrrole compound.

Description

Method for synthesizing 4-formylpyrrole derivative by silver catalysis and application
Technical Field
The invention belongs to the field of organic chemical synthesis, and particularly relates to a method for synthesizing a 4-formylpyrrole derivative by silver catalysis and application thereof.
Background
Pyrrole is a very important organic compound widely existing in drug molecules, natural products, pesticides and functional material molecules, and has wide biological activity and medicinal value, so that the preparation method thereof is one of hot spots of organic synthesis research. Researches show that some pyrrole compounds have the effects of resisting tumor, resisting virus and the like. Compounds containing pyrrole and pyrrolidine skeletons are widely used in many medicaments, for example, 10Z-HYMENIALDISINE is a natural bioactive pyrrole alkaloid which is also a pan-kinase inhibitor and has a certain anticancer activity. Clindamycin (CLINDAMYCIN) is an antibiotic drug that can inhibit the synthesis of bacterial proteins by binding to ribosomes, thereby exerting antibacterial activity. In the pesticide field, pyrrole compounds have certain insecticidal and bactericidal activities, for example, chlorfenapyr (Chlorfenapyr) is an aryl pyrrole nitrile insecticidal and acaricidal agent, and the pyrrole compounds have wider application fields as representatives of recommended pesticide varieties for disease and pest control of nuisanceless agricultural products. Therefore, studies are being made on how to develop an effective method for synthesizing pyrroles.
Currently, existing methods for synthesizing pyrrole have some drawbacks, such as: narrow substrate range, harsh reaction conditions, low product yield and the like, does not accord with the atom economy, and lacks practical value. Therefore, the development of a practical method for synthesizing the 1-naphthylamine compound has important significance.
Disclosure of Invention
The invention aims to provide a method for synthesizing a 4-formylpyrrole derivative by silver catalysis and application thereof, wherein the method has the advantages of mild reaction process, simplicity, convenience, safety, easiness in operation and high yield, and the 4-formylpyrrole derivative synthesized by the method can be further converted into an N-sulfonylated pyrrole compound.
In order to achieve the above purpose, the invention adopts the following technical scheme: a method for synthesizing 4-formylpyrrole derivatives by silver catalysis comprises the following specific steps: adding an alkenyl nitrone compound of a formula 1 and an isocyanoacetate compound of a formula 2 as reaction raw materials into an organic solvent, adding alkali, adding argon for protection under the catalysis of metallic silver salt, stirring at 80 ℃ for reaction, and performing TLC tracking reaction until the reaction is complete, thereby preparing the 4-formylpyrrole derivative of the compound of the formula 3 after the treatment of a reaction solution;
Wherein the molar ratio between the alkenyl nitrone compound and the isocyanoacetate is 1:1, a step of;
the molar ratio between the metallic silver salt and the alkenyl nitrone compound is 1:5, a step of;
The organic solvent is one of 1, 4-dioxane, N-dimethylformamide and dimethyl sulfoxide;
The alkali is one of cesium carbonate, potassium phosphate and potassium carbonate;
the metal silver salt is one of silver carbonate, silver oxide, silver triflate and silver p-toluenesulfonate;
The structural formula of the alkenyl nitrone compound of the formula 1 is In formula 1, R 1 is hydrogen, halogen, or methyl;
the structural formula of the compound isocyanoacetate of the formula 2 is In the formula 2, R is Me or Et;
The structural formula of the 4-formylpyrrole derivative of the compound of formula 3 is In formula 3, R 1 is hydrogen, halogen, or methyl; r is Me or Et.
Preferably, the ratio of the volume of the organic solvent to the molar amount of the alkenyl nitrone compound of formula 1 is 6mL:1mmol.
Preferably, the base is cesium carbonate, and the molar ratio between the base and the alkenyl nitrone compound of formula 1 is 2:1, a step of;
preferably, the metallic silver salt is silver oxide.
Preferably, the organic solvent is 1, 4-dioxane.
Preferably, the developing reagent used for the TLC follow-up reaction is 3:1 petroleum ether/ethyl acetate.
Further, the post-treatment method of the reaction liquid comprises the following steps: after the reaction is finished, the reaction is quenched by water, extracted by ethyl acetate, then the organic phase is backwashed by water, dried by anhydrous sodium sulfate, distilled under reduced pressure, separated by silica gel column chromatography, distilled under reduced pressure, and dried to obtain the 4-formylpyrrole derivative of the compound of the formula 3.
Preferably, the volume ratio of the eluent adopted by the silica gel column chromatography is 4:1 petroleum ether/ethyl acetate.
In order to achieve the above purpose, the invention also adopts the technical scheme that: the application of the 4-formylpyrrole derivative synthesized by the method for synthesizing the 4-formylpyrrole derivative by silver catalysis in converting the 4-formylpyrrole derivative into the N-sulfonylated pyrrole compound of the formula 5 comprises the following specific steps: adding 4-formylpyrrole derivative of formula 3 and p-toluenesulfonyl chloride of formula 4 as reaction raw materials into organic solvent, adding alkali and catalyst, stirring at room temperature for reaction, tracking TLC to complete, and processing the reaction solution to obtain N-sulfonylpyrrole compound of formula 5, wherein the structural formula isIn formula 5, R 1 is hydrogen, halogen, or methyl; r is Me or Et.
Preferably, the catalyst is TBAHS, the base is KOH, and the organic solvent is DCM; the post-treatment method of the reaction liquid comprises the following steps: after the reaction, the reaction was quenched with water, extracted with DCM, the organic phases were combined, and then the organic phases were backwashed with water, dried over anhydrous sodium sulfate, filtered under reduced pressure, and then subjected to silica gel column chromatography to obtain the N-sulfonylated pyrrole compound of formula 5.
Compared with the prior art, the invention has the following beneficial effects:
According to the invention, metal silver salt is selected as a catalyst, alkenyl nitrone compounds and isocyanoacetate are used as raw materials, and 4-formylpyrrole compounds are synthesized by a one-pot cycloaddition reaction method; the method has the advantages of simple operation, easily obtained reagents, mild reaction conditions, environment-friendly reaction system, easy separation and purification of products, high yield, suitability for synthesizing various highly functionalized 4-formylpyrrole compounds, and particular suitability for large-scale industrial production. Application studies prove that the 4-formylpyrrole compound can be further converted into N-sulfonylated pyrrole compound.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of 1 H-NMR of 4-formylpyrrole 3a prepared in example 1;
FIG. 2 is a nuclear magnetic resonance spectrum of 13 C-NMR of 4-formylpyrrole 3a prepared in example 1;
FIG. 3 is a nuclear magnetic resonance spectrum of 1 H-NMR of 4-formylpyrrole 3b prepared in example 2;
FIG. 4 is a nuclear magnetic resonance spectrum of 13 C-NMR of 4-formylpyrrole 3b prepared in example 2;
FIG. 5 is a nuclear magnetic resonance spectrum of 1 H-NMR of 4-formylpyrrole 3c prepared in example 3;
FIG. 6 is a nuclear magnetic resonance spectrum of 13 C-NMR of 4-formylpyrrole 3C prepared in example 3;
FIG. 7 is a nuclear magnetic resonance spectrum of 1 H-NMR of 4-formylpyrrole 3d prepared in example 4;
FIG. 8 is a nuclear magnetic resonance spectrum of 13 C-NMR of 4-formylpyrrole 3d prepared in example 4;
FIG. 9 is a nuclear magnetic resonance spectrum of 1 H-NMR of 4-formylpyrrole 3e prepared in example 5;
FIG. 10 is a nuclear magnetic resonance spectrum of 13 C-NMR of 4-formylpyrrole 3e prepared in example 5;
FIG. 11 is a nuclear magnetic resonance spectrum of 1 H-NMR of 4-formylpyrrole 3f prepared in example 6;
FIG. 12 is a nuclear magnetic resonance spectrum of 13 C-NMR of 4-formylpyrrole 3f prepared in example 6.
FIG. 13 is a nuclear magnetic resonance spectrum of 1 H-NMR of 3g of 4-formylpyrrole prepared in example 7;
FIG. 14 is a nuclear magnetic resonance spectrum of 13 C-NMR of 3g of 4-formylpyrrole prepared in example 7;
FIG. 15 is a nuclear magnetic resonance spectrum of 1 H-NMR of N-sulfonylated pyrrole compound 5 prepared in example 8;
FIG. 16 is a nuclear magnetic resonance spectrum of 13 C-NMR of N-sulfonylpyrrole compound 5 obtained in example 8.
Detailed Description
The present invention will be described in further detail with reference to examples.
In the examples described below, unless otherwise indicated, alkenyl nitrones, isocyanoacetates, metallic silver salts and other agents are commercially available or are available in a manner reported in the known literature.
Example 1
Preparation of 4-formylpyrrole derivatives 3a
To a 10mL reaction tube equipped with a magnetic stirring apparatus, (1Z, 2E) -N, 3-diphenylprop-2-en-1-imine oxide 1a (0.112 g,0.5 mmol), silver oxide (0.023 g,0.1 mmol), cesium carbonate (0.325 g,1 mmol), argon shield, and finally 1, 4-dioxane (3 mL) and ethyl isocyanoacetate 2a (54. Mu.L, 0.5 mmol) were added, after stirring uniformly, they were placed in an 80℃oil bath to continue stirring, TLC (developing solvent V Petroleum ether :V Acetic acid ethyl ester =3:1) detected substrate disappearance, and the reaction was completed; the reaction solution was poured into water (30 mL), extracted with ethyl acetate (3×10 mL), the organic phases were combined, then the organic phase was backwashed with water (3×10 mL), dried over anhydrous sodium sulfate, filtered off with suction, distilled under reduced pressure, and the like to give a viscous solid, which was finally subjected to silica gel column chromatography (eluent V Petroleum ether :V Acetic acid ethyl ester =4:1) to give a white solid, which was confirmed by NMR, MS to be 4-formylpyrrole compound 3a, the yield of which was 84%.
The hydrogen spectrum and the carbon spectrum are shown in fig. 1 and 2, and the spectrum analysis data are as follows 3a:
White solid ;1H NMR(CDCl3,400MHz):δH9.80(brs,1H,NH),9.66(s,1H),7.65(d,J＝3.2Hz,1H),7.48–7.36(m,5H),4.21(q,J＝7.2Hz,2H),1.15(t,J＝14Hz,3H).( figure 1);13C NMR(CDCl3,101MHz):δC13C NMR(101MHz,CHLOROFORM-D)δ187.1,160.7,133.1,131.5,130.7,127.9,127.7,125.8,125.3,120.6,60.8,13.9.( figure 2);HRMS(ESI-TOF,m/z):calcd for C14H13NO3[M+H]+,244.0968;found,244.0977.
Example 2
1B was used instead of 1a in example 1, and the yield was 67% under the same conditions as in example 1.
The hydrogen spectrum and the carbon spectrum are shown in fig. 3 and 4, and the spectrum analysis data are as follows 3b:
White solid ;1H NMR(CDCl3,400MHz):δH9.70(brs,1H,NH),9.66(s,1H),7.64(d,J＝3.2Hz,1H),7.41–7.36(m,4H),4.22(q,J＝7.2Hz,2H),1.19(t,J＝14Hz,3H).( figure 3);13C NMR(CDCl3,101MHz):δC13C NMR(101MHz,CHLOROFORM-D)δ186.5,160.6,134.0,132.0,131.4,130.1,127.9,126.1,125.7,120.8,62.5,14.0.( figure 4);HRMS(ESI-TOF,m/z):calcd for C14H12ClNO3[M+H]+,278.0578;found,278.0582.
Example 3
1C was used instead of 1a in example 1, and the yield was 69% under the same conditions as in example 1.
The hydrogen spectrum and the carbon spectrum are shown in fig. 5 and 6, and the spectrum analysis data are as follows 3c:
White solid ;1H NMR(CDCl3,400MHz):δH 9.97(brs,1H,NH),9.57(s,1H),7.66(d,J＝3.2Hz,1H),7.48(d,J＝7.6Hz,1H),7.37–7.32(m,3H),4.22–4.01(m,2H),1.07(t,J＝14.4Hz,3H).( figure 5);13C NMR(CDCl3,101MHz):δC 13C NMR(101MHz,CHLOROFORM-D)δ186.2,160.6,134.1,132.1,131.5,129.3,129.2,128.9,126.1,125.7,125.7,121.8,60.9,14.4.( figure 6);HRMS(ESI-TOF,m/z):calcd for C14H12ClNO3[M+H]+,278.0578;found,278.0585.
Example 4
1D was used instead of 1a in example 1, and the yield was 85% under the same conditions as in example 1.
The hydrogen spectrum and the carbon spectrum are shown in fig. 7 and 8, and the spectrum analysis data are as follows 3d:
white solid ;11H NMR(CDCl3,400MHz):δH 9.70(brs,1H,NH),9.56(s,1H),7.67(s,1H),7.65(s,1H),7.38–7.28(m,2H),7.28(s,1H),4.22–4.01(m,2H),1.06(t,J＝14.4Hz,3H).( figure 7);13C NMR(CDCl3,101MHz):δC 13C NMR(101MHz,CHLOROFORM-D)δ186.2,160.7,133.8,133.7,132.4,131.9,129.5,126.7,125.7,125.4,124.4,60.9,13.7.( figure 8);HRMS(ESI-TOF,m/z):calcd for C14H12BrNO3[M+H]+,322.0073;found,322.0081.
Example 5
1E was used instead of 1a in example 1, and the yield was 76% under the same conditions as in example 1.
The hydrogen spectrum and the carbon spectrum are shown in fig. 9 and 10, and the spectrum analysis data are as follows 3e:
White solid ;1H NMR(CDCl3,400MHz):δH 9.67(s,1H),9.64(brs,1H,NH),7.63(d,J＝3.2Hz,1H),7.32(d,J＝8.0Hz,2H),7.22(d,J＝7.6Hz,2H),4.22(q,J＝6.8Hz,2H),2.41(s,3H),1.19(t,J＝14.4Hz,3H).( figure 9);13C NMR(CDCl3,101MHz):δC 13C NMR(101MHz,CHLOROFORM-D)δ187.2,160.6,137.8,133.3,130.6,128.4,125.9,125.1,60.8,21.3,14.0.( figure 10);HRMS(ESI-TOF,m/z):calcd for C15H15NO3[M+H]+,258.1125;found,258.1136.
Example 6
1F was used instead of 1a in example 1, and the yield was 67% under the same conditions as in example 1.
The hydrogen spectrum and the carbon spectrum are shown in fig. 11 and 12, and the spectrum analysis data is as follows 3f:
White solid ;1H NMR(CDCl3,400MHz):δH 10.01(brs,1H,NH),9.48(s,1H),7.66(s,1H),7.31–7.27(m,2H),7.23-7.18(m,2H),4.19–4.01(m,2H),2.14(s,3H),1.04(t,J＝14.8Hz,3H).( figure 11);13C NMR(CDCl3,101MHz)δC(101MHz,CHLOROFORM-D)δ160.7,147.6,137.3,132.6,130.6,130.4,129.7,129.4,129.0,128.0,126.4,125.3,121.3,120.4,117.0,60.4,20.1,13.8.( figure 12);HRMS(ESI-TOF,m/z):calcd for C15H15NO3[M+H]+,258.1125;found,258.1129.
Example 7
2B was used instead of 2a in example 1, and the yield was 66% under the same conditions as in example 1.
The hydrogen spectrum and the carbon spectrum are shown in fig. 13 and 14, and the spectrum analysis data is as follows, 3g:
white solid ;1H NMR(CDCl3,400MHz)δH 9.66(s,1H),9.58(brs,1H,NH),7.66(s,1H),7.44-7.41(m,5H),3.74(s,3H).( figure 13);13C NMR(CDCl3,101MHz)δC 13C NMR(101MHz,CHLOROFORM-D)δ13C NMR(101MHz,CHLOROFORM-D)δ187.0,133.2,130.6,128.0,127.8,125.9,125.2,120.3,51.7.( figure 14);HRMS(ESI-TOF,m/z):calcd for C13H11NO3[M+H]+,230.0812;found,230.0815.
Example 8
The 4-formylpyrrole derivative can be further converted into N-sulfonylated pyrrole compound 5, the compound has wide application, can be used as an intermediate product of various special chemical derivatives, is an important raw material for producing various pyrrole compounds, and simultaneously, the tertiary amine compound is an important organic synthesis intermediate, has important effects in natural product synthesis and organic drug synthesis, and the synthesized 4-formylpyrrole derivative can be further converted into N-sulfonylated pyrrole compound, thereby providing a novel method for synthesizing the N-sulfonylated pyrrole compound; the reaction synthesis route is as follows:
To a 10mL reaction tube equipped with a magnetic stirring apparatus were added 4-formylpyrrole 3a (24 mg,0.1 mmol), p-toluenesulfonyl chloride 4 (23 mg,0.12 mmol), KOH (11 mg,0.2 mmol), TBAHS (2 mg,5% mmol), and finally DCM (2 mL), and after stirring uniformly, the mixture was reacted at room temperature. TLC (developing reagent V Petroleum ether :V Acetic acid ethyl ester =10:1) detects substrate disappearance and reaction is completed. The reaction was poured into water (30 mL), extracted with DCM (3×10 mL), the organic phases were combined, then the organic phase was backwashed with water (3×10 mL), dried over anhydrous sodium sulfate, filtered off under reduced pressure, distilled off under reduced pressure to give a viscous solid, which was finally chromatographed on a silica gel column (eluent V Petroleum ether :V Acetic acid ethyl ester =15:1) to give a white solid 5 in 88% yield.
The hydrogen spectrum and the carbon spectrum are shown in fig. 15 and 16, and the spectrum analysis data are as follows:
1H NMR(CDCl3,400MHz)δH 9.67(s,1H),8.20(s,1H),7.99(d,J＝6.4Hz,2H),7.42-7.36(m,5H),7.30-7.28(m,2H),4.07(q,J＝7.2Hz,2H),2.47(s,3H),0.093(t,J＝7.2Hz,3H).( Fig. 15);13C NMR(CDCl3,101MHz)δ13C NMR(101MHz,CHLOROFORM-D)δ186.0,160.0,146.2,134.6,133.6,130.7,129.9,129.8,129.5,128.8,128.2,127.9,124.6,123.9,61.5,21.8,13.4.( fig. 16).

Claims (10)

1. A method for synthesizing a 4-formylpyrrole derivative by silver catalysis is characterized by comprising the following specific steps: adding alkenyl nitrone compounds of the formula 1 and isocyanoacetate of the formula 2 serving as reaction raw materials into an organic solvent, adding alkali under the catalysis of metal silver salt, adding argon for protection, stirring at 80 ℃ for reaction, and performing TLC tracking reaction until the reaction is complete, thereby obtaining the 4-formylpyrrole derivatives of the formula 3 after the treatment of reaction liquid;
Wherein the molar ratio between the alkenyl nitrone compound and the isocyanoacetate is 1:1, a step of;
the molar ratio between the metallic silver salt and the alkenyl nitrone compound is 1:5, a step of;
The organic solvent is one of 1, 4-dioxane, N-dimethylformamide and dimethyl sulfoxide;
The alkali is one of cesium carbonate, potassium phosphate and potassium carbonate;
the metal silver salt is one of silver carbonate, silver oxide, silver triflate and silver p-toluenesulfonate;
The structural formula of the alkenyl nitrone compound of the formula 1 is In formula 1, R 1 is hydrogen, halogen, or methyl;
the structural formula of the compound isocyanoacetate of the formula 2 is In formula 2, R is selected from Me or Et;
The structural formula of the 4-formylpyrrole derivative of the compound of formula 3 is In formula 3, R 1 is hydrogen, halogen, or methyl; r is Me or Et.
2. The method for synthesizing the 4-formylpyrrole derivative by silver catalysis according to claim 1, wherein the ratio of the volume of the organic solvent to the molar amount of the alkenyl nitrone compound of the formula 1 is 6 mL/1 mmol.
3. The method for synthesizing the 4-formylpyrrole derivative by silver catalysis according to claim 1 or 2, wherein the base is cesium carbonate, and the molar ratio between the base and the alkenyl nitrone compound of formula 1 is 2:1.
4. A method for the catalytic synthesis of 4-formylpyrrole derivatives, according to claim 1 or 2, characterised in that the metallic silver salt is silver oxide.
5. A method for the catalytic synthesis of 4-formylpyrrole derivatives, according to claim 1 or 2, characterised in that the organic solvent is 1, 4-dioxane.
6. A method for the silver-catalyzed synthesis of 4-formylpyrrole derivatives according to claim 1 or 2, wherein the developing reagent used for the TLC follow-up reaction is 3:1 petroleum ether/ethyl acetate.
7. The method for synthesizing the 4-formylpyrrole derivative by silver catalysis according to claim 1 or 2, wherein the method for post-treatment of the reaction solution is as follows: after the reaction is finished, the reaction is quenched by water, extracted by ethyl acetate, then the organic phase is backwashed by water, dried by anhydrous sodium sulfate, distilled under reduced pressure, separated by silica gel column chromatography, distilled under reduced pressure, and dried to obtain the 4-formylpyrrole derivative of the compound of the formula 3.
8. The method for synthesizing the 4-formylpyrrole derivative by silver catalysis according to claim 7, wherein the eluent used in the silica gel column chromatography is in a volume ratio of 4:1 petroleum ether/ethyl acetate.
9. The use of a 4-formylpyrrole derivative synthesized by a method for synthesizing a 4-formylpyrrole derivative under silver catalysis as claimed in claim 1 for converting the 4-formylpyrrole derivative into a compound of formula 5, N-sulfonylated pyrrole, comprising the steps of: adding 4-formylpyrrole derivative of formula 3 and p-toluenesulfonyl chloride of formula 4 as reaction raw materials into organic solvent, adding alkali and catalyst, stirring at room temperature for reaction, tracking TLC to complete, and processing the reaction solution to obtain N-sulfonylpyrrole compound of formula 5, wherein the structural formula isIn formula 5, R 1 is hydrogen, halogen, or methyl; r is Me or Et.
10. The use according to claim 9, wherein the catalyst is TBAHS, the base is KOH, and the organic solvent is DCM; the post-treatment method of the reaction liquid comprises the following steps: after the reaction, the reaction was quenched with water, extracted with DCM, the organic phases were combined, and then the organic phases were backwashed with water, dried over anhydrous sodium sulfate, filtered under reduced pressure, and then subjected to silica gel column chromatography to obtain the N-sulfonylated pyrrole compound of formula 5.
CN202410349988.6A 2024-03-26 Method for synthesizing 4-formylpyrrole derivative by silver catalysis and application Pending CN118271227A (en)

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