CN111484454B - Method for preparing 5-hydroxyimidazole through CuI catalyzed multi-component reaction - Google Patents
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Abstract
The invention discloses a method for preparing 5-hydroxyimidazole by CuI catalyzed multi-component reaction, and relates to the field of pharmaceutical chemistry. The method takes arylamidine, alkynal and water as reaction substrates, and CuI as a catalyst to perform multi-component cyclization reaction, and the 5-hydroxyimidazole compound is obtained by constructing C-N and C-O bonds through one-step reaction and high regioselectivity. The preparation method is green and environment-friendly, the preparation process is simple and easy to operate, and the preparation cost is low; the reaction condition is mild, the application range of the reaction substrate is wide, the regioselectivity is good, and the yield is good; the preparation time is short, and various types of hydroxyl imidazole compounds can be quickly synthesized.
Description
Technical Field
The invention relates to the field of medicinal chemistry, in particular to a method for preparing 5-hydroxyimidazole by CuI catalyzed multi-component reaction.
Background
Imidazole ring is an important high-polarity aromatic heterocyclic compound and widely distributed in the fields of natural products, application medicines, functional materials and the like. Imidazole compounds have a wide range of biological activities, such as antibacterial, anticancer, antifungal, antagonist and phosphatase inhibition. The compound can be used as a medical intermediate to synthesize various complex medicines and imidazole medicines, such as over-the-counter metronidazole, prescription ornidazole, prescription metronidazole and the like. The metal complex can be used as a raw material of a plurality of functional materials, can be used as an organic small molecule catalyst to catalyze partial organic reactions, and is also an important component of a plurality of metal enzyme complexes and a plurality of carbene ligands and synthetic precursors of environment-friendly ionic liquid. Besides, the method can be used for synthesizing a cross-linking agent, a curing agent and the like, and has wide application.
The classical method for the synthesis of imidazoles is the Debus-Radziszewski reaction (e.g. (a) Debus, H. Ueber di einwirkung des amoniaks auf glyoxal. Ann. chem. Pharm.1858,107, 199-208. (b) Radziszewski, B. Dtsch, B.Br. Radziszewski: Ueber di condensation des lophilins und Verwender Verbindung. Ber. Dtsch. chem. ges. 2,15, 1493-1496.). Currently, a number of transition metal catalysis methods are used to prepare imidazole derivatives, such as iron catalysis, copper catalysis, zinc catalysis, silver catalysis, gold catalysis, palladium catalysis, nanocatalysis, and the like.
The multicomponent reaction refers to a process of continuous reaction between three or more reaction components coexisting in the same reaction mixture. In order for the multicomponent reaction to proceed efficiently, the components must be compatible and not capable of undergoing other irreversible reactions to form other products or byproducts. The method is simple to operate, the atom utilization rate is greatly improved, and the diversity and complexity of the product enable the method to be widely applied to synthesis of compounds with complex structures and pharmacological activity. The great wall develops a new method for efficiently synthesizing a polysubstituted imidazole compound by a three-component reaction of aryl amidine, phenylpropargyl aldehyde and alcohol under the catalysis of silver. It screens the conditions for optimal yield of the reaction: aryl amidine, alkynal and alcohol are used as reaction substrates, silver acetate is used as a catalyst, p-toluenesulfonic acid is used as an additive, and the reaction is carried out for 10 hours at 100 ℃ under the condition of nitrogen (Wang great wall, aryl amidine participates in multi-component reaction to construct imidazole derivatives). The method has relatively simple steps and is green and environment-friendly, but silver acetate is used as a catalyst, the cost is high, an additive is required to promote the reaction, nitrogen is required to be injected, the preparation conditions are harsh, the reaction needs to be carried out for 10 hours at 100 ℃, the temperature is high, the consumed time is long, and certain influence is caused on the application of the reaction.
In view of the above, the present application provides a method for forming an imidazole derivative through a multi-component reaction catalyzed by CuI, in which a multi-component cyclization reaction is performed under the condition that aryl amidine, aryl alkynal and water can be heated in a solvent by using CuI as a catalyst, so as to obtain a 5-hydroxyimidazole compound with high regioselectivity. The method overcomes the defects of harsh conditions, narrow substrate application range, multi-step synthesis and the like in the prior art for preparing hydroxyl molecules, has mild preparation conditions, greatly simplifies the preparation process, shortens the preparation time and saves the preparation cost.
Disclosure of Invention
According to the invention, CuI is used as a catalyst, aryl amidine, aryl alkynal and water can generate multicomponent cyclization reaction under the heating condition in a solvent, and C-N and C-O bonds are constructed by one-step reaction, so that the 5-hydroxy imidazole compound is obtained with high regioselectivity. The method has mild preparation conditions, greatly simplifies the preparation process, shortens the preparation time and saves the preparation cost.
In order to achieve the above object, the present invention provides a method for preparing 5-hydroxyimidazole by multicomponent reaction, wherein aryl amidine, alkynal and water are used as reaction substrates, CuI is used as a catalyst, and a cyclization reaction is performed to prepare a 5-hydroxyimidazole compound, wherein the formula is as follows:
in the formula, Ar in the compound 11And Ar2Is aryl, and the R group in the compound 2 is aryl or alkyl;
preferably, compound 1 is selected from any one of the following compounds:
further preferably, compound 1 is selected from any one of the following compounds:
still further, compound 1 is selected from the following compounds:
preferably, compound 2 is selected from any one of the following compounds:
further preferably, compound 2 is selected from the following compounds:
the molar ratio of the arylamidine to the alkynal is 1-3: 1; preferably 1: 1.
The volume molar ratio of the water to the alkynal is 1:1-3, preferably 1: 2;
the molar ratio of the CuI to the arylamidine is 0.01:1-0.1:1, and more preferably 0.03: 1.
The solvent in the formula is one or more of dimethyl sulfoxide, xylene, acetonitrile and toluene, and dimethyl sulfoxide is preferred.
Wherein the molar ratio of the solvent to the volume of the alkynal is 5 to 15mL/mmol, preferably 10 mL/mmol.
The temperature of the cyclization reaction is 75 to 85 ℃ and preferably 80 ℃.
The time for the cyclization reaction is 3.5 to 4.5 hours, preferably 4 hours.
Compared with the prior art, the invention has the following beneficial effects:
(1) the preparation method is green and environment-friendly, the preparation process is simple and easy to operate, and the preparation cost is low;
(2) the reaction condition is mild, the application range of the reaction substrate is wide, the regioselectivity is good, and the yield is good;
(3) the preparation time is short, and various types of hydroxyl imidazole compounds can be quickly synthesized.
Detailed Description
The present invention will be further explained with reference to specific examples in order to make the technical means, the technical features, the technical objectives and the effects of the present invention easier to understand, but the following examples are only preferred embodiments of the present invention, and not all embodiments of the present invention. Based on the embodiments in the implementation, other embodiments obtained by those skilled in the art without any creative efforts belong to the protection scope of the present invention.
In the following examples, unless otherwise specified, all the procedures and equipment used were conventional procedures and equipment used was conventional equipment.
In the following examples, CuI was purchased from research Inc. under the trade designation 7681-65-4.
Example 1
45.3mg (0.2mmol) of the arylamidine shown below, 26.0mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL stirred tube, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, the mixture is stirred at 80 ℃ for 4 hours, washed and chromatographed on silica gel to give the desired product in 60% yield.
1H NMR(400MHz,CDCl3)7.42-7.27(m,9H),7.25-7.14(m,6H),6.88(s,1H), 5.57(s,1H),3.18(s,1H).
13C NMR(100MHz,CDCl3)141.3,136.8,132.1,132.0,131.9,130.0,129.3, 128.9,128.5,128.4,128.4,128.3,128.3,128.2,128.2,128.1,128.1,127.8,127.7, 126.4,126.4,67.6.
HR-MALDI-MS m/z calcd.for C22H19N2O[M+H]+:327.1492,found: 327.1494.
Example 2
48.1mg (0.2mmol) of the arylamidine shown below, 26.0mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL stirred tube, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, stirring is carried out at 80 ℃ for 4 hours, and the desired product is isolated by chromatography on silica gel after washing with water in 62% yield.
1H NMR(400MHz,CDCl3)7.30(d,J＝6.1Hz,2H),7.23-7.12(m,10H),6.86 (s,3H),5.53(s,1H),3.85(s,1H),2.24(s,3H).
13C NMR(100MHz,CDCl3)141.5,139.4,136.8,131.9,130.1,129.6,129.0, 128.8,128.5,128.3,128.2,128.1,128.1,128.0,128.0,128.0,127.6,127.5,127.4, 126.5,125.3,67.6,21.1.
HR-MALDI-MS m/z calcd.for C23H21N2O[M+H]+:341.1648,found: 341.1653.
Example 3
48.1mg (0.2mmol) of the arylamidine shown below, 26.0mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL stirred tube, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, the mixture is stirred at 80 ℃ for 4 hours, washed and chromatographed on silica gel to give the desired product in 60% yield.
1H NMR(400MHz,CDCl3)7.28-7.27(m,4H),7.26-7.19(m,4H),7.17-7.13(m, 1H)7.09-7.03(m，4H),7.00-6.97(m,1H),6.88(s,1H),5.61(s,1H),3.24(s,1H), 2.15(s,3H).
13C NMR(100MHz,CDCl3)141.4,138.0,136.3,135.6,130.9,130.2,130.0, 128.8,128.8,128.8,128.3,128.2,128.2,128.2,127.8,127.8,127.7,126.5,126.5, 126.5,125.0,67.8,20.1.
HR-MALDI-MS m/z calcd.for C23H21N2O[M+H]+:341.1648,found: 341.1643.
Example 4
45.2mg (0.2mmol) of the arylamidine shown below, 26.0mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL stirred tube, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, the mixture is stirred at 80 ℃ for 4 hours, washed and chromatographed on silica gel to give the desired product in 75% yield.
1H NMR(400MHz,CDCl3)7.32(d,J＝7.0Hz,2H),7.24-7.15(m,9H), 6.92-6.72(m,4H),5.56(s,1H),3.99(s,1H),3.63(s,3H).
13C NMR(100MHz,CDCl3)160.0,147.8,141.5,137.8,137.2,130.0,129.9, 128.2,128.2,128.2,128.1,128.1,128.1,128.1,128.1,127.7,127.6,126.5,120.5, 115.0,113.7,67.6,55.3.
HR-MALDI-MS m/z calcd.for C23H21N2O2[M+H]+:357.1598,found: 357.1603.
Example 5
45.6mg (0.2mmol) of the arylamidine shown below, 26.0mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL stirred tube, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, the mixture is stirred at 80 ℃ for 4 hours, washed and chromatographed on silica gel to give the desired product in 73% yield.
1H NMR(400MHz,CDCl3)7.50-7.34(m,7H),7.11-7.06(m,6H),6.88(s,1H), 5.64(s,1H),4.97(s,1H),2.40(s,3H).
13C NMR(100MHz,CDCl3)162.2(d,J＝249.3Hz),142.9,141.4,141.4,138.3, 135.8,132.8,130.11(d,J＝8.6Hz),129.1,128.8,128.8,128.6,128.2,128.0,128.0, 128.0,127.8,127.4,126.3,126.3,115.96(d,J＝22.9Hz),67.2,21.1.
HR-MALDI-MS m/z calcd.for C23H20FN2O[M+H]+:359.1554,found: 359.1552.
Example 6
57.6mg (0.2mmol) of the arylamidine shown below, 26.0mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL test tube with stirrer, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, stirring is carried out at 80 ℃ for 4 hours, and the desired product is isolated by chromatography on silica gel after washing with water in 76% yield.
1H NMR(400MHz,CDCl3)7.37(d,J＝8.8Hz,2H),7.22-7.16(m,6H), 7.06-7.01(m,2H),6.99-6.84(m,3H),6.74(s,1H),5.48(s,1H),4.25(s,1H),2.21(s, 3H).
13C NMR(100MHz,CDCl3)141.2,137.9,135.9,132.2,132.2,132.2,129.9, 129.9,129.6,129.2,128.1,128.1,128.1,128.1,128.0,127.5,126.3,126.3,126.3, 125.3,122.6,67.2,21.3.
HR-MALDI-MS m/z calcd.for C23H20BrN2O[M+H]+:419.0754,found: 419.0754.
Example 7
45.3mg (0.2mmol) of the arylamidine shown below, 28.8mg (0.2mmol) of the alkynal substrate and water (0.1mL) are introduced into a 25mL stirred tube, 2mL of dimethyl sulfoxide are added at room temperature, 1.1mg (0.006mmol) of CuI are added, the mixture is stirred at 80 ℃ for 4 hours, washed and chromatographed on silica gel to give the desired product in 65% yield.
1H NMR(400MHz,CDCl3)7.84(s,1H),7.45(s,1H),7.39-7.28(m,6H), 7.22-7.11(m,3H),7.08-6.97(m,3H),6.89(s,1H),5.50(s,1H),4.84(s,1H),2.27(s, 1H).
13C NMR(100MHz,CDCl3)141.3,137.7,136.9,130.6,130.2,129.5,129.2, 128.7,128.5,128.3,128.3,128.3,128.1,128.0,128.0,128.0,127.8,127.1,123.5, 123.0,121.7,67.7,21.3.
HR-MALDI-MS m/z calcd.for C23H21N2O[M+H]+:341.1648,found: 341.1642.
Example 8
In contrast to example 6, CuI was used in an amount of 0.002mmol, which was the same as the rest, 54% yield.
1H NMR(400MHz,CDCl3)7.37(d,J＝8.8Hz,2H),7.22-7.16(m,6H), 7.06-7.01(m,2H),6.99-6.84(m,3H),6.74(s,1H),5.48(s,1H),4.25(s,1H),2.21(s, 3H).
13C NMR(100MHz,CDCl3)141.2,137.9,135.9,132.2,132.2,132.2,129.9, 129.9,129.6,129.2,128.1,128.1,128.1,128.1,128.0,127.5,126.3,126.3,126.3, 125.3,122.6,67.2,21.3.
HR-MALDI-MS m/z calcd.for C23H20BrN2O[M+H]+:419.0754,found: 419.0754.
Example 9
In contrast to example 6, CuI was used in an amount of 0.02mmol, the remainder being the same, 75% yield.
1H NMR(400MHz,CDCl3)7.37(d,J＝8.8Hz,2H),7.22-7.16(m,6H), 7.06-7.01(m,2H),6.99-6.84(m,3H),6.74(s,1H),5.48(s,1H),4.25(s,1H),2.21(s, 3H).
13C NMR(100MHz,CDCl3)141.2,137.9,135.9,132.2,132.2,132.2,129.9, 129.9,129.6,129.2,128.1,128.1,128.1,128.1,128.0,127.5,126.3,126.3,126.3, 125.3,122.6,67.2,21.3.
HR-MALDI-MS m/z calcd.for C23H20BrN2O[M+H]+:419.0754,found: 419.0754.
Comparative example 1
In contrast to example 6, CuI was replaced with the same amount of Cu (OAc)2The rest were the same, 40% yield.
1H NMR(400MHz,CDCl3)7.37(d,J＝8.8Hz,2H),7.22-7.16(m,6H), 7.06-7.01(m,2H),6.99-6.84(m,3H),6.74(s,1H),5.48(s,1H),4.25(s,1H),2.21(s, 3H).
13C NMR(100MHz,CDCl3)141.2,137.9,135.9,132.2,132.2,132.2,129.9, 129.9,129.6,129.2,128.1,128.1,128.1,128.1,128.0,127.5,126.3,126.3,126.3, 125.3,122.6,67.2,21.3.
HR-MALDI-MS m/z calcd.for C23H20BrN2O[M+H]+:419.0754,found: 419.0754.
The present invention is not limited to the above-described preferred embodiments, but rather, the present invention is to be construed broadly and cover all modifications, equivalents, and improvements falling within the spirit and scope of the present invention.
Claims (5)
1. A method for preparing a compound 4 by a multi-component reaction is characterized in that the compound 4 is prepared by a cyclization reaction by taking aryl amidine, alkynal and water as reaction substrates and CuI as a catalyst, and the expression is as follows:
wherein Ar in the compound 1 in the formula1And Ar2Is aryl, and the R group in the compound 2 is aryl or alkyl; the solvent is dimethyl sulfoxide; the reaction temperature is 80 ℃, the reaction time is 4h, the molar ratio of the aryl amidine to the alkynal is 1:1, and the volume molar ratio of the water to the alkynal is 1:2 (mL: mmol); the molar ratio of CuI to arylamidine is 0.01:1-0.1: 1.
2. A method for preparing a compound 4 by a multi-component reaction is characterized in that the compound 4 is prepared by a cyclization reaction by taking aryl amidine, alkynal and water as reaction substrates and CuI as a catalyst, and the expression is as follows:
wherein the solvent is dimethyl sulfoxide; the reaction temperature is 80 ℃, the reaction time is 4h, the molar ratio of the aryl amidine to the alkynal is 1:1, and the volume molar ratio of the water to the alkynal is 1:2 (mL: mmol); the molar ratio of the CuI to the arylamidine is 0.01:1-0.1:1,
wherein compound 1 is selected from any one of the following compounds:
wherein compound 2 is selected from any one of the following compounds:
3. the method of claim 2, wherein compound 1 is selected from any one of the following compounds:
4. the method of claim 3, wherein compound 1 is selected from the group consisting of:
5. the method of claim 2, wherein compound 2 is selected from the group consisting of:
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008004117A1 (en) * | 2006-07-06 | 2008-01-10 | Pfizer Products Inc. | Selective azole pde10a inhibitor compounds |
| CN103275011A (en) * | 2013-06-13 | 2013-09-04 | 南京工业大学 | Novel method for synthesizing imidazolidine heterocycle |
| CN107162982A (en) * | 2017-06-19 | 2017-09-15 | 广东药科大学 | Imidazole compounds with anticancer activity and derivatives thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008004117A1 (en) * | 2006-07-06 | 2008-01-10 | Pfizer Products Inc. | Selective azole pde10a inhibitor compounds |
| CN103275011A (en) * | 2013-06-13 | 2013-09-04 | 南京工业大学 | Novel method for synthesizing imidazolidine heterocycle |
| CN107162982A (en) * | 2017-06-19 | 2017-09-15 | 广东药科大学 | Imidazole compounds with anticancer activity and derivatives thereof |
Non-Patent Citations (2)
| Title |
|---|
| Substrate-Controlled Selectivity Switch in a Three-Component Reaction: A Ag-Catalyzed Strategy for the Synthesis of Functionalized Imidazoles;Changcheng Wang et al.;《The Journal of Organic Chemistry》;20170816;第82卷;第9144-9153页 * |
| Synthesis of Benz-Fused Azoles via C‑Heteroatom CouplingReactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands;Nidhi Mishra et al.;《ACS Combinatorial Science》;20190403;第21卷;第389-399页 * |
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