CN113929651A - Method for synthesizing alpha-pyrone compound - Google Patents
Method for synthesizing alpha-pyrone compound Download PDFInfo
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- CN113929651A CN113929651A CN202111343068.6A CN202111343068A CN113929651A CN 113929651 A CN113929651 A CN 113929651A CN 202111343068 A CN202111343068 A CN 202111343068A CN 113929651 A CN113929651 A CN 113929651A
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
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Abstract
The invention relates to an alpha-pyrone compound and a synthesis method thereof, wherein DMAP is used for catalyzing bromoacetophenone and cyclopropenone to generate a [3+3] cyclization reaction under an alkaline heating condition to generate the alpha-pyrone compound. Because the alpha-pyrone drugs have wide clinical application, the invention provides a new method for synthesizing the alpha-pyrone compounds, and is expected to provide a new direction for the clinical application of the pyrone. The synthesis method disclosed by the invention is simple to operate, the raw materials are easy to obtain, the reaction conditions are mild, no metal catalyst is needed, the product is easy to separate and purify, the technical difficulties of complicated steps and complex raw materials of the synthesis method in the prior art are solved, the synthesis method is a breakthrough in the prior synthesis technology, and the synthesis method has high application value.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthetic method of an alpha-pyrone compound.
Background
Pyrones are ketone derivatives of pyrans, which are widely found in nature, mainly in plants. Substances such as benzopyrans (chromenes), chromones, coumarins, flavones, isoflavones, anthocyanidins, and the like, are all considered to be derivatives of pyrones. Pyrone has two isomers which are alpha-pyrone and gamma-pyrone, wherein the alpha-pyrone is hexatomic ring unsaturated lactone, widely exists in a plurality of natural products, and has extremely wide application in the fields of medicines, pesticides, perfumes, dyes and the like, the alpha-pyrone also has good biological activity, and the alpha-pyrone is also an important intermediate in organic synthesis. The conjugated diene structure of the conjugated diene is easy to generate Diels-Alder reaction.
Due to the structural particularity of alpha-pyrone, the synthesis of alpha-pyrone has become a hot spot of research at home and abroad in recent years. The synthesis method of alpha-pyrone reported in the past has the limitations of long steps, complex raw materials, troublesome operation, high temperature condition, expensive metal catalyst and the like. Therefore, a new method for synthesizing the alpha-pyrone compound is developed, and the method becomes urgent.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a synthetic method of an alpha-pyrone compound, which has simple operation, does not need a metal catalyst and has easily obtained raw materials.
In order to achieve the purpose, the invention adopts the following technical scheme to realize the purpose:
the invention discloses a synthesis method of an alpha-pyrone compound, which is characterized in that bromoacetophenone and cyclopropenone are subjected to [3+3] cyclization reaction under the catalysis of 4-dimethylaminopyridine under the alkaline heating condition to synthesize the alpha-pyrone compound, wherein:
the structural formula of bromoacetophenone is as follows:
the structural formula of cyclopropenone is as follows:
the structural formula of the synthesized alpha-pyrone compound is as follows:
wherein R is1,R2,R3The group is alkyl or aryl.
Preferably, the method for synthesizing the alpha-pyrone compound comprises the following steps:
1) under the protection of nitrogen, adding bromoacetophenone and cyclopropenone into an alkaline organic solvent, stirring under the catalysis of 4-dimethylaminopyridine for 8-14 h under the heating condition, and cooling to room temperature after the reaction is finished;
2) and filtering, concentrating and purifying the reaction system by column chromatography to obtain the alpha-pyrone compound.
Further preferably, the reaction molar ratio of the cyclopropenone, the bromoacetophenone and the 4-dimethylaminopyridine is 1.0 (1.0-1.5) to 1.0-1.5.
More preferably, the reaction charge ratio of the cyclopropenone to the organic solvent is 0.2mmol (1-2) mL.
Further preferably, the organic solvent is 1, 4-dioxane, made basic by the addition of potassium hydroxide.
Further preferably, the heating temperature is 50 to 65 ℃.
Still more preferably, the heating temperature is 60 ℃.
Further preferably, in the step 1), the column chromatography adopts a silica gel chromatographic column, and the weight ratio of petroleum ether: ethyl acetate ═ 20:1 volume ratio through the column.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a synthetic method of an alpha-pyrone compound, which is characterized in that bromoacetophenone and cyclopropenone are subjected to a [3+3] cyclization reaction under the catalysis of DMAP and the alkaline heating condition to efficiently synthesize the alpha-pyrone compound. In the synthetic method, the adopted reaction raw materials of cyclopropenone and bromoacetophenone are both convenient to obtain, and the problem of complex raw material source in the prior art is solved; the reaction product is subjected to a [3+3] cyclization reaction under an alkaline heating condition to obtain a target product, the reaction condition is consistent and does not need to be adjusted, and a metal catalyst does not need to be added in the reaction system, so that on one hand, impurities such as metal and the like cannot be introduced into the system, on the other hand, the separation and purification processes of the product are simple, and the synthesis method is simple in operation and mild in reaction condition.
Furthermore, in the synthesis method provided by the invention, the reaction is carried out at 60 ℃, so that the high conversion rate of the alpha-pyrone compound can be ensured, and the convenience and the safety of the operation can be ensured.
Drawings
FIG. 1 is a diagram showing a reaction mechanism for synthesizing an α -pyrone compound according to the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It is noted that the terms "comprises" and "comprising," and any variations thereof, in the description and claims of this invention, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements expressly listed, but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
The invention is described in further detail below with reference to the accompanying drawings:
the invention discloses a synthesis method of an alpha-pyrone compound, which is characterized in that bromoacetophenone and cyclopropenone are subjected to a [3+3] cyclization reaction under the condition of alkaline heating by DMAP catalysis to generate the alpha-pyrone compound.
The mechanism of the (3 + 3) cyclization reaction is that firstly bromoacetophenone and DMAP react to generate an intermediate A, then KOH pulls out hydrogen at a carbonyl alpha-position to generate a nitrogenous ylide B, the intermediate B and the intermediate C are subjected to tautomerization and attack on the side with smaller steric hindrance of cyclopropenone to generate an intermediate D, and the ketene structure E generated by DMAP leaving undergoes the (3 + 3) cyclization reaction to generate the final product alpha-pyrone. The reaction mechanism is shown in FIG. 1.
Bromoacetophenone and cyclopropenone are generated under the condition of alkaline heating, and the reaction formula is as follows:
in the above reaction formula, R1,R2,R3The groups are alkyl and aryl;
the method comprises the following steps: under the protection of nitrogen, bromoacetophenone and cyclopropenone are added into an alkaline organic solvent, and DMAP is catalyzed and stirred for 12 hours under the heating condition; after the reaction is finished, cooling to room temperature; filtering, rotary steaming, concentrating, and performing column chromatography to obtain alpha-pyrone compounds;
preferably, the ratio of the cyclopropenone A to the bromoacetophenone B in the method of the invention is 1: 1.5; the solvent adopted in the invention is 1, 4-dioxane; the mol ratio of the cyclopropenone A to the 1, 4-dioxane is as follows: 0.2 mmol/1-2 mL; the temperature adopted by the heating of the invention is 60 ℃;
example 1
Diphenylcyclopropenone (0.2mmol), 2-bromo-1-4- (trifluoromethoxy) acetophenone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol) were added to 100mg of 4A molecular sieve (for water removal, reaction was controlled under anhydrous conditions) and 1, 4-dioxane (2.0mL) under nitrogen, heated at 60 ℃ for 12h, after reaction was complete, cooled to room temperature, filtered, concentrated by vacuum distillation and purified by flash column chromatography (silica gel, mixture of petroleum ether/ethyl acetate, 20:1, v/v) to afford 67.3mg of the desired pure product in 82% yield as a yellow solid with melting point 134-136 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):7.93(d,J＝8.9Hz,2H,Ar-H),7.38–7.13 (m,13H,Ar-H),6.82(s,1H,Ar-H).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):162.4,156.7,152.5,150.7,137.5, 133.5,130.8,129.8,128.8,128.6,128.4,128.0,127.8,127.2,123.5,121.1,105.4.
IRνmax(neat):1697,1504，1266,1210,1150,833,,789，769,699cm-1.
HRMS(ESI)calcd for C24H15F3O3[M+H]+:409.1046,found:409.1048.
example 2
The procedure is as described in example 1, except that the substrates used are: diphenyl cyclopropenone (0.2mmol), 2-bromo-1-4- (trifluoromethyl) acetophenone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0mL) to obtain 59.5mg of product, yield of 76%, yellow solid of product, and melting point of 170-172 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):8.03(d,J＝8.2Hz,2H,Ar-H),7.74(d,J ＝8.3Hz,2H,Ar-H),7.32–7.15(m,10H,Ar-H),6.93(s,1H,Ar-H).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):162.2,156.3,152.2,137.3,134.5, 133.4,130.7,128.9,128.6,128.4,1278.0 128.0,126.0,125.9,125.7,124.3,106.3.
IRνmax(neat):1697,1537，1329,1160,1117,1072,831,789,699cm-1.
HRMS(ESI)calcd for C24H15F3O2[M+H]+:393.1097,found:393.1100
example 3
The procedure is as described in example 1, except that the substrates used are: diphenyl cyclopropenone (0.2mmol), 2-bromo-1-cyclohexylethanone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0mL) are heated at 65 ℃ to obtain 27.8mg of a product, the yield is 42%, the product is a white solid, and the melting point is 124-125 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):7.25–7.07(m,10H,Ar-H),6.13(s,1H, Ar-H),2.49(t,J＝11.6Hz,1H,CH),2.07(d,J＝13.2Hz,2H,CH2),1.86(d,J＝12.9 Hz,2H,CH2),1.75(d,J＝15.2Hz,1H,CH2),1.57–1.18(m,5H,CH2).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):167.89,163.63,152.84,137.97, 134.10,130.93,128.77,128.64,128.32,128.02,127.57,122.18,104.50,42.32,30.65, 25.87.
IRνmax(neat):2929,2853，1699,1634,1538,944,764,606,564cm-1.
HRMS(ESI)calcd for C23H22O2[M+H]+:331.1693,found:331.1690.
example 4
The procedure is as described in example 1, except that the substrates used are: 2-butyl-3-phenyl cyclopropenone (0.2mmol), bromoacetophenone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0mL) are heated at 55 ℃ to obtain 26.8mg of a product, the yield is 44%, the product is a yellow solid, and the melting point is 92-94 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):7.90–7.86(m,2H,Ar-H),7.49–7.41 (m,5H,Ar-H),7.38(m,1H,Ar-H),7.31–7.28(m,2H,Ar-H),6.67(m＝s,1H,Ar-H), 2.39(m 2H,CH2),1.51-1.55(m,2H,CH2),1.31–1.24(m,2H,CH2),0.83(t,J＝7.3 Hz,3H,CH3).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):162.65,158.22,155.66,134.13, 131.60,130.61,130.02,128.96,128.48,128.05,125.61,124.33,103.89,33.11,31.41, 22.53,13.80.
IRνmax(neat):2962,2927,1706,1627,1538,1451,1351,722,692cm-1.
HRMS(ESI)calcd for C21H20O2[M+H]+:305.1536,found:305.1537
example 5
The procedure is as described in example 1, except that the substrates used are: bis- (4-methylphenyl) cyclopropenone (0.2mmol), bromoacetophenone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol), heating at 50 ℃ and 100mg of 4A molecular sieve and 1, 4-dioxane (2.0mL) to obtain 26.2mg of a product, wherein the yield is 50%, the product is a yellow solid, and the melting point is 174-176 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):7.88(d,J＝9.7Hz,2H,Ar-H),7.63(d, J＝8.2Hz,2H,Ar-H),7.56(d,J＝7.2Hz,1H,Ar-H),7.47(d,J＝7.1Hz,3H,Ar-H), 7.25(d,J＝9.4Hz,2H,Ar-H),6.78(d,J＝7.2Hz,1H,Ar-H),2.39(s,3H,CH3).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):161.61,159.57,139.75,138.61, 131.95,131.35,130.71,129.25,129.02,128.08,125.81,125.53,101.85,21.36.
IRνmax(neat):1711,1622,1556,1495,1115,902,823,762,685cm-1.
HRMS(ESI)calcd for C18H14O2[M+H]+:263.1067,found:263.1066.
example 6
The procedure is as described in example 1, except that the substrates used are: 2-3-bis (4-methylphenyl) cyclopropenone (0.2mmol), bromoacetophenone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0mL) to obtain a product 42.2mg, wherein the yield is 59%, the product is a yellow solid, and the melting point is 158-160 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):7.90(m,2H,Ar-H),7.51–7.44(m,3H, Ar-H),7.08(d,J＝6.6Hz,8H,Ar-H),6.82(s,1H,Ar-H),2.32(d,J＝6.2Hz,6H, CH3).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):163.05,157.94,152.35,138.84, 137.46,135.07,131.60,131.07,130.77,130.67,129.17,128.99,128.86,128.75, 125.63,122.94,105.21,21.41.
IRνmax(neat):1701,1625,1531,1350,979,815,726,690,646cm-1.
HRMS(ESI)calcd for C25H20O2[M+H]+:353.1536,found:353.1536.
example 7
The procedure is as described in example 1, except that the substrates used are: 2-3-bis (4-fluorophenyl) cyclopropenone (0.2mmol), bromoacetophenone (0.3mmol), DMAP (20 mol%), KOH (0.3mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0mL) to obtain 64.1mg of a product, wherein the yield is 89%, the product is a yellow solid, and the melting point is 204-206 ℃. The structural formula is as follows:
1H NMR(400MHz,CDCl3)(δ,ppm):7.93–7.88(m,2H,Ar-H),7.51–7.46 (m,3H,Ar-H),7.20–7.12(m,4H,Ar-H),7.01–6.92(m,4H,Ar-H),6.80(s,1H,Ar- H).
13C{1H}NMR(400MHz,CDCl3；δ,ppm):164.09,164.05,163.51,162.61, 161.60,161.04,158.66,151.96,133.67,133.63,132.80,132.72,131.23,131.06, 130.78,130.69,129.62,129.58,129.11,125.72,122.16,115.93,115.72,115.46, 115.24,104.76.
IRνmax(neat):1687,1536,1351,1223,1157,842,762,557,543cm-1.
HRMS(ESI)calcd for C23H14F2O2[M+H]+:361.1035,found:361.1037.
the above-mentioned contents are only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and any modification made on the basis of the technical idea of the present invention falls within the protection scope of the claims of the present invention.
Claims (8)
1. A synthetic method of an alpha-pyrone compound is characterized in that the alpha-pyrone compound is synthesized by catalyzing bromoacetophenone and cyclopropenone to generate a [3+3] cyclization reaction under the condition of alkaline heating by 4-dimethylaminopyridine, wherein:
the structural formula of bromoacetophenone is as follows:
the structural formula of cyclopropenone is as follows:
the structural formula of the synthesized alpha-pyrone compound is as follows:
wherein R is1,R2,R3The group is alkyl or aryl.
2. The method for synthesizing α -pyrone compounds according to claim 1, comprising the steps of:
1) under the protection of nitrogen, adding bromoacetophenone and cyclopropenone into an alkaline organic solvent, stirring under the catalysis of 4-dimethylaminopyridine for 8-14 h under the heating condition, and cooling to room temperature after the reaction is finished;
2) and filtering, concentrating and purifying the reaction system by column chromatography to obtain the alpha-pyrone compound.
3. The method for synthesizing the alpha-pyrones according to claim 2, wherein the reaction molar ratio of the cyclopropenone, the bromoacetophenone and the 4-dimethylaminopyridine is 1.0 (1.0-1.5) to 1.0-1.5.
4. The method for synthesizing the alpha-pyrone compound according to claim 2, wherein the reaction charge ratio of the cyclopropenone to the organic solvent is 0.2mmol (1-2) mL.
5. The method for synthesizing α -pyrones according to claim 2, wherein the organic solvent is 1, 4-dioxane and is adjusted to be basic by adding potassium hydroxide.
6. The method for synthesizing the α -pyrone compound according to claim 2, wherein the heating temperature is 50 to 65 ℃.
7. The method for synthesizing α -pyrone compounds according to claim 6, wherein the heating temperature is 60 ℃.
8. The method for synthesizing α -pyrone compounds according to claim 2, wherein in step 1), the column chromatography is performed using a silica gel column, and the ratio of petroleum ether: ethyl acetate ═ 20:1 volume ratio through the column.
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| CN116354914A (en) * | 2023-04-10 | 2023-06-30 | 河南科技大学 | Triphenylsubstituted pyrone derivative and synthetic method and application thereof |
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