CN108689947B - Method for promoting synthesis of dihydropyrimidinones compound by using dihydrogen phosphate ionic liquid - Google Patents
Method for promoting synthesis of dihydropyrimidinones compound by using dihydrogen phosphate ionic liquid Download PDFInfo
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
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- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
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- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
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- B01J31/0298—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature the ionic liquids being characterised by the counter-anions
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Abstract
The invention discloses a method for promoting synthesis of dihydropyrimidinone compounds by using dihydrogen phosphate ionic liquid, and belongs to the technical field of synthesis of dihydropyrimidinone compounds. The technical scheme provided by the invention has the key points that: the target product dihydropyrimidinone compound is prepared by stirring and reacting N-propargyl amide compounds and p-toluenesulfonyl azide serving as reaction substrates, CuI serving as a catalyst and dihydrogen phosphate ionic liquid serving as a cocatalyst and a solvent at 70 ℃. The dihydrogen phosphate ionic liquid has the advantages of simple preparation process, low price, easy obtainment and high catalytic activity, and effectively promotes the reaction; the reaction does not need to add alkali and ligand, and can obtain ideal reaction yield in a short time in the air atmosphere; the reaction system has no corrosion to equipment and no special requirement on a reaction vessel, and the operation and the post-treatment process of the catalytic system are simple.
Description
Technical Field
The invention belongs to the technical field of synthesis of dihydropyrimidinone compounds, and particularly relates to a method for promoting synthesis of dihydropyrimidinone compounds by using dihydrogen phosphate ionic liquid under the conditions of no alkali, no ligand and no need of organic solvent.
Background
DHPMs have a wide variety of pharmacological activities, and can be used as anticancer drugs or for treating schizophrenia, and have received extensive attention from researchers. The conventional methods for synthesizing dihydropyrimidin-4-one compounds are: condensation of beta-amino amides with aldehydes (Dzhavakhishvili S G, Gorobes N Y, Shishkina S V, et al. conversion of a thieno [2,3-d ]]pyrimidin-4-one scaffold via Regioselective Alkylation Reactions[J]Chem.2009,11(3),508-].Chem.2005,42,583), and the like. The coupling reaction of picric acid, aldehyde and guanidine carbonate can also produce 2-aminodihydropyrimidin-4-one (Mirza-Agahayan M, Baie Lashaki T, Rahimifard M, et al Amino-functionalized MCM-41 base-functionalized one-pot synthesis of2-Amino-5, 6-dihydropyrimidine-4 (3H) -ones [ J]Chem. Soc.2011,8(1), 280-286.). Wang subject group of Zhejiang university (Wang J, Lu P, Wang Y. copper-catalyzed cascade preparation of dimeric amide-4-ones from N- (Prop-2-yn-1-yl) amides and azides [ J]Journal of Organic Chemistry 2013,78:8816-8820.) in acetonitrile solvent using piperidine to provide an alkaline environment, CuI to catalyze propargylamide and TsN under argon protection3Performing cycloaddition reaction to generate dihydropyrimidinone. Lin et al (Rajagopal B. Cu (I) -catalyzed synthesis of hydropyrimid-4-ones fabricated the preparation of beta-and beta3-amino acid analogues[J]Journal of Organic Chemistry 2014,79: 1254-S1264.) use methylene chloride, CuI and K2CO3Carrying out copper-catalyzed azide-alkyne cycloaddition reaction to synthesize dihydropyrimidinone and derivatives thereof. In the methods, inorganic or organic alkali and organic solvent such as dichloromethane, acetonitrile and the like are inevitably used, the reaction system needs inert gas for protection, the experimental conditions are harsh, the post-treatment process is relatively complex, and the reaction system has the defects of low atom economy and the like.
In recent decades, with the introduction of green chemistry, ionic liquids have been vigorously developed as a new and green catalyst and solvent, and the research thereof has been more and more active, and the variety thereof has been increasing. Due to the rich variety and designability, people are often endowed with some special functions, and the method can be applied to many fields. Therefore, it has attracted a lot of attention in academia and industry. The ionic liquid has the characteristics of difficult volatilization, designability, high thermal stability and chemical stability, strong catalytic activity, recyclability and the like, and has wide application prospect in the synthesis and catalysis industry. However, no article or related patent reports the application of the compound in promoting the synthesis of dihydropyrimidinones.
Disclosure of Invention
The invention solves the technical problem of providing a cheap, easily obtained, convenient and efficient method for promoting the synthesis of dihydropyrimidinones by using dihydrogen phosphate ionic liquid, wherein the dihydrogen phosphate ionic liquid is used as a cocatalyst and a solvent at the same time, and the synthesis of dihydropyrimidinones is effectively promoted under mild conditions.
The invention adopts the following technical scheme for solving the technical problems, and the method for promoting the synthesis of dihydropyrimidinone compounds by using the dihydrogen phosphate ionic liquid is characterized by comprising the following specific processes: with N-propargyl amides and p-toluenesulfonyl azide (TsN)3) Stirring and reacting at 70 ℃ to obtain a target product dihydropyrimidinone compound by taking CuI as a reaction substrate and a dihydrogen phosphate ionic liquid as a catalyst and a cocatalyst and a solvent, wherein the reaction equation in the synthesis process is as follows:
wherein R ═ Ph, 4-MeC6H4、3-MeC6H4、2-MeOC6H4、4-FC6H4、2-ClC6H4、4-ClC6H4Or 3,5-MeC6H4The structural formula of the dihydrogen phosphate ionic liquid is as follows:
preferably, the feeding molar ratio of the N-propargyl amide compound, the p-toluenesulfonyl azide and the CuI to the ionic liquid is 1:1.2:0.05-0.15: 0.5-1.5.
Preferably, the reaction time of the synthesis process is 30 min.
The invention relates to a method for promoting synthesis of dihydropyrimidinone compounds by using dihydrogen phosphate ionic liquid, which is characterized by comprising the following specific steps: sequentially adding 0.05mmol of dihydrogen phosphate ionic liquid, 0.01mmol of CuI, 0.1mmol of N-propargylamide compound and 0.12mmol of p-toluenesulfonylazide into a reaction vessel, stirring and mixing uniformly, placing the mixture into an oil bath, heating and stirring at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to spin-dry the solvent, and recrystallizing the crude product to obtain the target product dihydropyrimidinone compound.
Compared with the prior art, the invention has the following advantages:
1. the dihydrogen phosphate ionic liquid has simple preparation process, low cost, easy obtainment and high catalytic activity;
2. the reaction does not need to add alkali and ligand, and can obtain ideal reaction yield in a short time in the air atmosphere;
3. the reaction system has no corrosion to equipment and no special requirement on a reaction vessel, and the operation and the post-treatment process of the catalytic system are simple.
Detailed Description
The present invention is described in further detail below with reference to examples, but it should not be construed that the scope of the above subject matter of the present invention is limited to the following examples, and that all the technologies realized based on the above subject matter of the present invention belong to the scope of the present invention.
Example 1
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl benzamide and 0.12mmol of p-toluenesulfonyl azide, uniformly stirring on a magnetic stirrer, then placing the reaction flask in an oil bath, heating and stirring at 70 ℃, reacting for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to remove the solvent, and recrystallizing the crude product (N-hexane: ethyl acetate: 7:1, v/v) to obtain the target product with the yield of 78%.
Example 2
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-4-methylbenzamide and 0.12mmol of p-toluenesulfonylazide under magnetic forceStirring and mixing the materials uniformly on a stirrer, then placing the reaction flask in an oil bath, heating and stirring the materials at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC (thin layer chromatography), extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling the solvent under reduced pressure, and recrystallizing the crude product (normal hexane: ethyl acetate ═ 7:1, v/v) to obtain the target product with the yield of 82%.
Example 3
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-3-methylbenzamide and 0.12mmol of p-toluenesulfonyl azide, stirring and mixing uniformly on a magnetic stirrer, then placing a reaction flask in an oil bath, heating and stirring at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to remove a rotary drying solvent, and recrystallizing a crude product (N-hexane: ethyl acetate ═ 7:1, v/v) to obtain a target product, wherein the yield is 80%.
Example 4
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-2-methoxybenzamide and 0.12mmol of p-toluenesulfonyl azide, stirring and mixing uniformly on a magnetic stirrer, then placing the reaction flask in an oil bath, heating and stirring at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to remove the solvent in a rotary manner, and recrystallizing the crude product (normal hexane: ethyl acetate is 7:1, v/v) to obtain the target product, wherein the yield is 73%.
Example 5
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-4-fluorobenzamide and 0.12mmol of p-toluenesulfonyl azide, stirring and uniformly mixing on a magnetic stirrer, then placing a reaction flask in an oil bath, heating and stirring at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, and combiningAnd the dichloromethane phase was combined, the solvent was distilled off under reduced pressure, and the crude product was recrystallized (n-hexane: ethyl acetate 7:1, v/v) to obtain the objective product in a yield of 85%.
Example 6
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-2-chlorobenzamide and 0.12mmol of p-toluenesulfonyl azide, stirring and mixing uniformly on a magnetic stirrer, then placing a reaction flask in an oil bath, heating and stirring at 70 ℃, reacting for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to remove a rotary drying solvent, and recrystallizing a crude product (N-hexane: ethyl acetate ═ 7:1, v/v) to obtain a target product, wherein the yield is 85%.
Example 7
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-4-chlorobenzamide and 0.12mmol of p-toluenesulfonyl azide, stirring and mixing uniformly on a magnetic stirrer, then placing the reaction flask in an oil bath, heating and stirring at 70 ℃, reacting for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to remove the solvent, and recrystallizing the crude product (N-hexane: ethyl acetate ═ 7:1, v/v) to obtain the target product with the yield of 80%.
Example 8
0.05mmol of DMEA was added to a 5mL round-bottomed flask][H2PO4]And 0.01mol of CuI, 0.1mmol of N-propargyl-3, 5-dimethyl benzamide and 0.12mmol of p-toluenesulfonyl azide, stirring and mixing uniformly on a magnetic stirrer, then placing the reaction flask in an oil bath, heating and stirring at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to spin-dry the solvent, and recrystallizing the crude product (N-hexane: ethyl acetate is 7:1, v/v) to obtain the target product with the yield of 75%.
TABLE 1 Effect of Birdhydrogen phosphate Ionic liquid addition on the promotion of Synthesis of dihydropyrimidinones
aReaction conditions are as follows: n-propargyl benzamide (0.1mmol), p-toluenesulfonyl azide (0.12mmol) and dihydrogen phosphate ionic liquid [ DMEA ]][H2PO4]The Molar ratio is IL: n-propargylbenzamide; the reaction time is 30 min;bisolated yield.
TABLE 2 Effect of different ionic liquids on the promotion of the Synthesis of dihydropyrimidinones
aReaction conditions are as follows: n-propargylbenzamide (0.2mmol), p-toluenesulfonylazide (TsN)3) (0.24mmol), CuI (10% mol), IL (1.5eq), reaction temperature 50 ℃;bisolated yield.
The foregoing embodiments illustrate the principles, principal features and advantages of the invention, and it will be understood by those skilled in the art that the invention is not limited to the foregoing embodiments, which are merely illustrative of the principles of the invention, and that various changes and modifications may be made therein without departing from the scope of the principles of the invention.
Claims (4)
1. The method for promoting synthesis of dihydropyrimidinone compounds by using dihydrogen phosphate ionic liquid is characterized by comprising the following specific steps: the method comprises the following steps of taking N-propargyl amide compounds and p-toluenesulfonyl azide as reaction substrates, CuI as a catalyst, dihydrogen phosphate ionic liquid as a cocatalyst and a solvent, stirring and reacting at 70 ℃ to obtain a target product dihydropyrimidinone compound, wherein the reaction equation in the synthesis process is as follows:
wherein R = H, 4-Me, 3-Me, 2-OMe, 4-F, 2-Cl, 4-Cl or 3,5-DiMe, and the structural formula of the dihydrogen phosphate ionic liquid is as follows:
。
2. the method for promoting synthesis of dihydropyrimidinones from dihydrogen phosphate ionic liquid according to claim 1, wherein: the feeding molar ratio of the N-propargyl amide compound, the p-toluenesulfonyl azide and the CuI to the ionic liquid is 1:1.2:0.05-0.15: 0.5-1.5.
3. The method for promoting synthesis of dihydropyrimidinones from dihydrogen phosphate ionic liquid according to claim 1, wherein: the reaction time in the synthesis process was 30 min.
4. The method for promoting the synthesis of dihydropyrimidinones from dihydrogen phosphate ionic liquid according to claim 1, which comprises the following specific steps: sequentially adding 0.05mmol of dihydrogen phosphate ionic liquid, 0.01mmol of CuI, 0.1mmol of N-propargylamide compound and 0.12mmol of p-toluenesulfonylazide into a reaction vessel, stirring and mixing uniformly, placing the mixture into an oil bath, heating and stirring at 70 ℃ for reaction for 30min, tracking and monitoring the whole reaction process by TLC, extracting the reaction mixture by using secondary water and dichloromethane after the reaction is finished, combining dichloromethane phases, distilling under reduced pressure to spin-dry the solvent, and recrystallizing the crude product to obtain the target product dihydropyrimidinone compound.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102225910A (en) * | 2011-04-01 | 2011-10-26 | 新疆大学 | Preparation method of Bronsted acidic ionic liquid based on isonicotinic acid cation |
| CN103193715A (en) * | 2013-03-28 | 2013-07-10 | 浙江大学 | Preparation method of 5,6-dihydropyrimidone derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102225910A (en) * | 2011-04-01 | 2011-10-26 | 新疆大学 | Preparation method of Bronsted acidic ionic liquid based on isonicotinic acid cation |
| CN103193715A (en) * | 2013-03-28 | 2013-07-10 | 浙江大学 | Preparation method of 5,6-dihydropyrimidone derivative |
Non-Patent Citations (3)
| Title |
|---|
| Copper-Catalyzed Cascade Preparation of Dihydropyrimidin-4-ones from N‑(Prop-2-yn-1-yl)amides and Azides;Jinjin Wang et al.;《J. Org. Chem.》;20130731;第78卷;第8816-8820页 * |
| Cu(I)-Catalyzed Synthesis of Dihydropyrimidin-4-ones toward the Preparation of β- and β3‑Amino Acid Analogues;Basker Rajagopal et al.;《J. Org. Chem.》;20140113;第79卷;第1254-1264页 * |
| 功能化离子液体在Cu/Ag催化的有机反应中的应用;杜春艳;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20190115(第2019年第01期);第29-37页 * |
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