CN113912555A - Synthesis method of 4-acyl-1, 2, 3-triazole compound - Google Patents
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- CN113912555A CN113912555A CN202111375220.9A CN202111375220A CN113912555A CN 113912555 A CN113912555 A CN 113912555A CN 202111375220 A CN202111375220 A CN 202111375220A CN 113912555 A CN113912555 A CN 113912555A
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Abstract
The invention discloses a synthesis method of a 4-acyl-1, 2, 3-triazole compound, belonging to the technical field of organic chemical synthesis. The synthesis method of the 4-acyl-1, 2, 3-triazole compound comprises the following steps: mixing one or more of aryl ketone, aryl alcohol, heterocyclic ketone and heterocyclic alcohol, organic azide and a solvent to obtain a mixture, sequentially adding copper salt, 2,6, 6-tetramethylpiperidine oxide, ligand 2,2' -dipyridine and base triethylamine into the mixture, and stirring to react at 90-100 ℃ to obtain the 4-acyl-1, 2, 3-triazole compound. The synthesis method does not need to use alkene or alkyne as raw materials and high-temperature and high-pressure reaction conditions, and the yield of the prepared 4-acyl-1, 2, 3-triazole compound is as high as 95 percent.
Description
Technical Field
The invention relates to the technical field of organic chemical synthesis, in particular to a synthesis method of a 4-acyl-1, 2, 3-triazole compound.
Background
The 1,2, 3-triazole compound is an important five-membered heterocyclic ring containing three N atoms, and the three N atoms are connected together, so that the 1,2, 3-triazole can exist stably and is not easy to be oxidized and reduced. Because the triazole ring has high electron cloud density and is easy to coordinate with metal, the 1,2, 3-triazole compound is a potential excellent ligand, and the obtained metal complex has good application in the aspects of light, electricity, magnetism and organic synthesis. Meanwhile, the 1,2, 3-triazole ring is a bioisostere of amide and has important application in pharmaceutical chemistry, and particularly 4-acyl-1, 2, 3-triazole compounds containing an alpha-ketotriazole structural unit are widely favored in drug design, and some of the compounds show good biological activity, such as cancer resistance, tuberculosis resistance and transglutaminase inhibition. Because the 1,2, 3-triazole compound has wide application in the fields of medicine synthesis, organic synthesis and catalysis, material science and the like, the synthesis method thereof is concerned.
Methods for producing 4-acyl-1, 2, 3-triazole compounds from various α, β -functionalized ketones and unsaturated hydrocarbons have been reported, for example, a method for obtaining 1,2, 3-triazole rings by 1, 3-dipolar cycloaddition of an organic azide and a terminal alkyne proposed by Huisgen, but the process requires a strong electron-withdrawing group attached to the azide or alkyne, and is carried out at a high temperature and a high pressure and for a long reaction time, and the product is a mixture of 1, 4-disubstituted and 1, 5-disubstituted triazoles, and thus its application is very limited.
Disclosure of Invention
The invention aims to overcome the technical defects, provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, and solves the technical problem that the 4-acyl-1, 2, 3-triazole compound is difficult to be efficiently prepared under the reaction condition of avoiding high temperature and high pressure in the prior art.
In order to achieve the technical purpose, the technical scheme of the invention provides a synthesis method of a 4-acyl-1, 2, 3-triazole compound, which comprises the following steps: mixing one or more of aryl ketone, aryl alcohol, heterocyclic ketone and heterocyclic alcohol, organic azide and a solvent to obtain a mixture, sequentially adding copper salt, 2,6, 6-tetramethylpiperidine oxide, ligand 2,2' -dipyridine and base triethylamine into the mixture, and stirring to react at 90-100 ℃ to obtain the 4-acyl-1, 2, 3-triazole compound.
Further, the heterocyclic ketone or the aryl ketone has the structural formula:
the heterocyclic alcohol or the aryl alcohol has a structural formula:
wherein R is1Is pyridine, furan, thiophene, naphthalene, benzene ring or aryl, and R is hydrogen or phenyl.
Further, the structural formula of the organic azide is as follows: r2-N3Wherein R is2Is aryl, phenyl or ester group.
Further, the copper salt is CuCl2，CuSO4，CuBr2，Cu(OAc)2，Cu(OTf)2，CuBr，CuCl,CuI,CuO,Cu(acac)2And Cu2One or more of O.
Further, the solvent is one or more of acetonitrile, dimethyl carbonate, tetrahydrofuran and toluene.
Further, the molar ratio of one or more of the heterocyclic ketone, the heterocyclic alcohol, the aryl ketone and the aryl alcohol to the organic azide is 1: 1-2.
Further, the molar ratio of the copper salt to the organic azide is 0.1: 1-2.
Further, the molar ratio of the organic azide to the 2,2,6, 6-tetramethylpiperidine oxide is 1-2: 0.2.
Further, the molar ratio of the organic azide to the triethylamine is (1-2) to (0.1-1).
Further, the stirring reaction time is 12-16 h.
Compared with the prior art, the invention has the beneficial effects that: one or more of heterocyclic ketone, heterocyclic alcohol, aryl ketone and aryl alcohol and organic azide are taken as raw materials, copper salt, TEMPO (2,2,6, 6-tetramethyl piperidine oxide), ligand 2,2' -dipyridine and base triethylamine are sequentially added to be stirred and reacted at 90-100 ℃ to generate oxidative dehydrogenation and oxidative cycloaddition reaction to obtain the 4-acyl-1, 2, 3-triazole compound, the reaction condition of high temperature and high pressure is not needed, and the yield of the 4-acyl-1, 2, 3-triazole compound is up to 95%.
Drawings
FIG. 1 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 1 of the present invention1And H, spectrum.
FIG. 2 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 1 of the present invention13And C, spectrum.
FIG. 3 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 2 of the present invention1And H, spectrum.
FIG. 4 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 2 of the present invention13And C, spectrum.
FIG. 5 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 3 of the present invention1And H, spectrum.
FIG. 6 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 3 of the present invention13And C, spectrum.
FIG. 7 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 4 of the present invention1And H, spectrum.
FIG. 8 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 4 of the present invention13And C, spectrum.
FIG. 9 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 6 of the present invention1And H, spectrum.
FIG. 10 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 6 of the present invention13And C, spectrum.
FIG. 11 is a drawing showing a preparation method of a 4-acyl-1, 2, 3-triazole compound produced in example 7 of the present invention1And H, spectrum.
FIG. 12 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 7 of the present invention13And C, spectrum.
FIG. 13 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 8 of the present invention1And H, spectrum.
FIG. 14 shows a process for preparing a 4-acyl-1, 2, 3-triazole compound obtained in example 8 of the present invention13And C, spectrum.
Detailed Description
The present embodiment provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of: mixing one or more of heterocyclic ketone, heterocyclic alcohol, aryl ketone and aryl alcohol, organic azide and a solvent to obtain a mixture, sequentially adding copper salt, 2,6, 6-tetramethylpiperidine oxide, a ligand 2,2' -dipyridine and base triethylamine into the mixture, and stirring and reacting at 90-100 ℃ for 12-16h to obtain a 4-acyl-1, 2, 3-triazole compound;
the heterocyclic ketone or the aryl ketone has a structural formula:
the heterocyclic alcohol or the aryl alcohol has a structural formula:
wherein R is hydrogen or phenyl, R1Is pyridine, furan, thiophene, naphthalene, benzene ring or aryl compound; the structural formula of the organic azide is as follows: r2-N3Wherein R is2Is aryl, phenyl or ester group; the copper salt is CuCl2，CuSO4，CuBr2，Cu(OAc)2，Cu(OTf)2，CuBr，CuCl,CuI,CuO,Cu(acac)2And Cu2O, wherein the solvent is one or more of acetonitrile, dimethyl carbonate, tetrahydrofuran and toluene; the organic azide is benzyl azide; the molar ratio of one or more of aryl ketone, aryl alcohol, heterocyclic ketone and heterocyclic alcohol to the organic azide is 1: 1-2; the molar ratio of the copper salt to the organic azide is 0.1: 1-2; the molar ratio of the organic azide to the 2,2,6, 6-tetramethylpiperidine oxide is 1-2: 0.2, the molar ratio of the organic azide to the triethylamine is (1-2): 0.1-1, and the molar ratio of the organic azide to the ligand is (1-2): 0.1-0.2.
The reaction process is illustrated by taking phenylpropanol as an example, and the details are as follows:
firstly, under the catalytic conditions of copper salt, ligand 2,2' -dipyridine, base triethylamine, oxidant and air, an alcohol compound is converted into a ketone compound in a quantitative yield; then the ketone compound generates a ketene intermediate with high activity under standard conditions; finally, the intermediate and organic azide are subjected to an oxidative cycloaddition reaction under the action of a catalyst to obtain the 4-acyl-1, 2, 3-triazole compound.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
This example provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of: 1.5mmol of propiophenone, 2.2mmol of benzyl azide and 2mL of dimethyl carbonate as a solvent were mixed to obtain a mixture, and 10% mol of Cu (OTf) was sequentially added to the mixture20.45mmol of 2,2,6, 6-tetramethylpiperidine oxide, 0.23mmol of ligand 2,2' -dipyridine and 0.6mmol of basic triethylamine were reacted at 90 ℃ under stirring in an air atmosphere for 15 hours to obtain a 4-acyl-1, 2, 3-triazole compound with a yield of 95%.
The reaction formula is as follows:
referring to FIGS. 1 and 2, the measured values of the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.43–8.40(m,2H),8.16(s,1H),7.63–7.57(m,1H),7.54–7.48(m,2H),7.42–7.38(m,3H),7.35–7.31(m,2H),5.61(s,2H)。
13C NMR(100MHz,CDCl3)δ185.6,148.4,136.5,133.7,133.3,130.6,129.3,129.2,128.4,128.2,77.3,77.0,76.7,54.5。
example 2
This example provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of:
benzyl butanone (1.30mmol) and benzyl azide (2.0mmol) were dissolved in DMC (2mL), and Cu (OTf) was added sequentially2(10 mol%), TEMPO (0.39mmol),2,2' -dipyridine (0.20mmol) and Et3N (0.52mmol), then warmed to 90 ℃ and stirred. After the reaction, saturated saline solution and ethyl acetate are sequentially added into the mixture for extraction, liquid separation is carried out, the organic phase is concentrated to obtain a crude product, and then column purification is carried out, wherein the yield is 93%.
The reaction formula is as follows:
referring to FIGS. 3 and 4, measured results of the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.59–8.12(m,2H),7.63–7.54(m,1H),7.54–7.44(m,2H),7.39–7.30(m,3H),7.24–7.15(m,2H),5.56(s,2H),2.55(s,3H)。
13C NMR(100MHz,CDCl3)δ187.5,143.7,139.3,137.3,133.9,132.8,130.5,129.1,128.5,128.1,127.2,51.7,9.5。
example 3
3-Phenylbenzyl ketone (0.95mmol) and benzyl azide (1.43mmol) were dissolved in DMC (2mL), Cu (OTf) was added sequentially2(10 mol%), TEMPO (0.29mmol),2,2' -dipyridine (0.14mmol) and Et3N (0.38mmol), then warmed to 90 ℃ and stirred. After the reaction is finished, saturated saline solution and ethyl acetate are sequentially added into the mixture for extraction, liquid separation is carried out, the organic phase is concentrated, a crude product is obtained and then column purification is carried out, and the yield is 86%.
The reaction formula is as follows:
referring to FIGS. 5 and 6, measured results of the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.36–8.24(m,2H),7.63–7.54(m,1H),7.50–7.43(m,5H),7.31–7.24(m,5H),7.12–7.01(m,2H),5.47(s,2H)。
13C NMR(100MHz,CDCl3)δ186.2,143.7,141.7,137.0,134.6,132.9,130.6,129.9,129.7,128.7,128.6,128.3,128.1,127.5,126.2,51.9。
example 4
Pyridine propanol (1.46mmol) and benzyl azide (2.20mmol) were dissolved in DMC (2mL), and Cu (OTf) was added sequentially2(10 mol%), TEMPO (0.44mmol),2,2' -dipyridine (0.22mmol) and Et3N (0.58mmol), then warmed to 90 ℃ and stirred. After the reaction is finished, adding saturated saline solution and ethyl acetate into the mixture in sequence for extraction, separating liquid, concentrating an organic phase to obtain a crude product, and purifying the crude product by a column, wherein the yield is 85%.
The reaction formula is as follows:
referring to FIGS. 7 and 8, measured results of the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.79(d,J＝4.7Hz,2H),8.31–7.99(m,3H),7.40–7.27(m,5H),5.58(s,2H)。
13C NMR(100MHz,CDCl3)δ184.4,150.4,147.4,142.3,133.4,129.2,129.1,128.5,128.2,123.2,54.4。
from examples 1-4, it can be seen that the target products obtained all have a high yield, up to 95%, and the present invention also attempts to prepare the target products using different copper salts, but the yields are relatively low, as detailed in examples 5-7:
example 5
This example provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of: mixing 1.3mmol of phenylbutanone, 2.0mmol of benzyl azide and 2mL of solvent toluene to obtain a mixture, and adding the mixture into the mixtureAdding 10mol percent of CuBr20.39mmol of 2,2,6, 6-tetramethylpiperidine oxide, 0.2mmol of ligand 2,2' -dipyridine and 0.52mmol of triethylamine are stirred and reacted for 16 hours at 100 ℃ under an air atmosphere, saturated saline and ethyl acetate are sequentially added into the mixture for extraction, liquid separation and organic phase concentration are carried out, crude products are obtained and then the crude products are purified by a column to obtain the 4-acyl-1, 2, 3-triazole compound, and the yield is 72 percent.
The reaction formula is as follows:
referring to FIGS. 9 and 10, measured results of the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.59–8.12(m,2H),7.63–7.54(m,1H),7.54–7.44(m,2H),7.39–7.30(m,3H),7.24–7.15(m,2H),5.56(s,2H),2.55(s,3H)。
13C NMR(100MHz,CDCl3)δ187.5,143.7,139.3,137.3,133.9,132.8,130.5,129.1,128.5,128.1,127.2,51.7,9.5。
example 6
This example provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of: 0.95mmol of 3-phenylbenzylketone, 1.43mmol of benzylazide and 2mL of dimethyl carbonate as solvent are mixed to give a mixture, and 10% mol of Cu (OAc) are added to the mixture in succession2After 0.29mmol of 2,2,6, 6-tetramethylpiperidine oxide, 0.14mmol of ligand 2,2' -dipyridine and 0.38mmol of triethylamine were reacted under stirring at 95 ℃ under an air atmosphere for 16 hours, the mixture was sequentially added with saturated saline and ethyl acetate to extract, followed by liquid separation and concentration of the organic phase, to obtain a 4-acyl-1, 2, 3-triazole compound with a yield of 70%.
The reaction formula is as follows:
combination drawing11 and 12, measured for the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.36–8.24(m,2H),7.63–7.54(m,1H),7.50–7.43(m,5H),7.31–7.24(m,5H),7.12–7.01(m,2H),5.47(s,2H)。
13C NMR(100MHz,CDCl3)δ186.2,143.7,141.7,137.0,134.6,132.9,130.6,129.9,129.7,128.7,128.6,128.3,128.1,127.5,126.2,51.9。
example 7
This example provides a method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of: 1.46mmol of pyridylpropanol, 2.2mmol of benzyl azide and 2mL of solvent toluene are mixed to obtain a mixture, 10% mol of CuCl, 0.44mmol of 2,2,6, 6-tetramethylpiperidine oxide, 0.22mmol of ligand 2,2' -dipyridine and 0.58mmol of triethylamine are sequentially added into the mixture, the mixture is stirred and reacted for 15 hours at the temperature of 100 ℃ under an air atmosphere, saturated saline and ethyl acetate are sequentially added into the mixture for extraction, liquid separation, organic phase concentration and column chromatography purification are carried out, and the 4-acyl-1, 2, 3-triazole compound is obtained, wherein the yield is 69%.
The reaction formula is as follows:
referring to FIGS. 13 and 14, measured results of the 4-acyl-1, 2, 3-triazole compound synthesized in this example1H and13c is as follows:
1H NMR(400MHz,CDCl3)δ8.79(d,J＝4.7Hz,2H),8.31–7.99(m,3H),7.40–7.27(m,5H),5.58(s,2H)。
13C NMR(100MHz,CDCl3)δ184.4,150.4,147.4,142.3,133.4,129.2,129.1,128.5,128.2,123.2,54.4。
the above-described embodiments of the present invention should not be construed as limiting the scope of the present invention. Any other corresponding changes and modifications made according to the technical idea of the present invention should be included in the protection scope of the claims of the present invention.
Claims (10)
1. A method for synthesizing a 4-acyl-1, 2, 3-triazole compound, comprising the steps of: mixing one or more of aryl ketone, aryl alcohol, heterocyclic ketone and heterocyclic alcohol, organic azide and a solvent to obtain a mixture, sequentially adding copper salt, 2,6, 6-tetramethylpiperidine oxide, ligand 2,2' -dipyridine and base triethylamine into the mixture, and stirring to react at 90-100 ℃ to obtain the 4-acyl-1, 2, 3-triazole compound.
2. The method of synthesizing a 4-acyl-1, 2, 3-triazole compound of claim 1, wherein the heterocyclic ketone or aryl ketone has the structural formula:
the heterocyclic alcohol or the aryl alcohol has a structural formula:
wherein R is1Is pyridine, furan, thiophene, naphthalene, benzene ring or aryl, and R is hydrogen or phenyl.
3. The method of synthesizing a 4-acyl-1, 2, 3-triazole compound of claim 1, wherein the organic azide has the formula: r2-N3Wherein R is2Is aryl, phenyl or ester group.
4. The method for synthesizing 4-acyl-1, 2, 3-triazole compound according to claim 1, wherein the copper salt is CuCl2，CuSO4，CuBr2，Cu(OAc)2，Cu(OTf)2，CuBr，CuCl,CuI,CuO,Cu(acac)2And Cu2One or more of O.
5. The method for synthesizing a 4-acyl-1, 2, 3-triazole compound according to claim 1, wherein the solvent is one or more of acetonitrile, dimethyl carbonate, tetrahydrofuran, and toluene.
6. The method for synthesizing a 4-acyl-1, 2, 3-triazole compound according to claim 1, wherein the molar ratio of the organic azide to one or more of aryl ketone, aryl alcohol, heterocyclic ketone and heterocyclic alcohol is 1: 1-2.
7. The method for synthesizing a 4-acyl-1, 2, 3-triazole compound according to claim 1, wherein the molar ratio of the copper salt to the organic azide is 0.1: 1-2.
8. The method for synthesizing a 4-acyl-1, 2, 3-triazole compound according to claim 1, wherein the molar ratio of the organic azide to the 2,2,6, 6-tetramethylpiperidine oxide is 1-2: 0.2.
9. The method for synthesizing a 4-acyl-1, 2, 3-triazole compound as claimed in claim 1, wherein the molar ratio of the organic azide to the triethylamine is (1-2): 0.1-1.
10. The method for synthesizing a 4-acyl-1, 2, 3-triazole compound according to claim 1, wherein the stirring reaction time is 12 to 16 hours.
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