CN113929651B - Method for synthesizing alpha-pyrone compound - Google Patents
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- 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
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Abstract
The invention relates to an alpha-pyrone compound and a synthesis method thereof, wherein the alpha-pyrone compound is generated by catalyzing bromoacetophenone and cyclopropanone to generate [3+3] cyclization reaction under alkaline heating condition through DMAP, and the novel method for efficiently synthesizing the alpha-pyrone compound has the advantages of simple operation, easily available raw materials and potential economic benefit. Because the alpha-pyrone medicine has wide clinical application, the invention provides a novel method for synthesizing the alpha-pyrone compound, which is expected to provide a novel direction for the clinical application of the pyrone. The synthesis method disclosed by the invention is simple to operate, easy to obtain raw materials, mild in reaction conditions, free of metal catalysts, easy to separate and purify products, solves the technical difficulties of complicated steps and complex raw materials of the synthesis method in the prior art, breaks through the prior synthesis technology, and has high application value.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a synthesis 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 benzopyran (chromene), chromone, coumarin, flavone, isoflavone, anthocyanin and the like can be considered derivatives of pyrone. The two isomers of the pyrone are divided into alpha-pyrone and gamma-pyrone, wherein the alpha-pyrone is a six-membered cyclic unsaturated lactone, is widely applied to a plurality of natural products, has extremely wide application in the fields of medicines, pesticides, perfumes, dyes and the like, has good biological activity, and is an important intermediate in organic synthesis. The conjugated diene structure of the catalyst is more prone to Diels-Alder reaction.
The synthesis of the alpha-pyrone is a hot spot for research at home and abroad in recent years due to the specificity of the alpha-pyrone structure. The synthesis method of alpha-pyrone reported in the past has the limitations of lengthy steps, complex raw materials, troublesome operation, high temperature conditions, expensive metal catalysts and the like. Based on the method, 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 in the prior art, the invention aims to provide a synthesis method of an alpha-pyrone compound, which is simple to operate, does not need a metal catalyst and has easily available raw materials.
In order to achieve the above purpose, the invention is realized by adopting the following technical scheme:
the invention discloses a synthesis method of an alpha-pyrone compound, which comprises the steps of catalyzing bromoacetophenone and cyclopropanone to generate [3+3] cyclization reaction under alkaline heating condition through 4-dimethylaminopyridine to synthesize the alpha-pyrone compound, wherein:
the bromoacetophenone has the following structural formula:
the structural formula of the cyclopropenone is as follows:
the structural formula of the synthesized alpha-pyrone compound is as follows:
wherein R is 1 ,R 2 ,R 3 The group is an alkyl or aryl group.
Preferably, the synthesis method of the alpha-pyrone compound comprises the following steps:
1) Adding bromoacetophenone and cyclopropenone into an alkaline organic solvent under the protection of nitrogen, and stirring for 8-14 h under the heating condition under the catalysis of 4-dimethylaminopyridine, and cooling to room temperature after the reaction is finished;
2) Filtering, concentrating and purifying the reaction system by column chromatography to obtain the alpha-pyrone compound.
It is further preferable that the reaction molar ratio of cyclopropenone, bromoacetophenone and 4-dimethylaminopyridine is 1.0 (1.0-1.5): 1.0-1.5.
Further preferably, the reaction charge ratio of cyclopropenone to organic solvent is 0.2mmol (1-2) mL.
Further preferably, the organic solvent is 1, 4-dioxane, which is 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 step 1), column chromatography is performed using a silica gel column chromatography using petroleum ether: ethyl acetate = 20: purifying by passing the mixture through a column according to the volume ratio of 1.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a synthesis method of an alpha-pyrone compound, which is characterized in that bromoacetophenone and cyclopropanone are subjected to [3+3] cyclization reaction under the condition of DMAP catalysis and alkaline heating to obtain the alpha-pyrone compound. In the synthesis method, the cyclopropenone and bromoacetophenone which are used as reaction raw materials are conveniently obtained, so that the problem of complex raw material sources in the prior art is solved; the target product is obtained by the cyclization reaction of [3+3] under the alkaline heating condition, the reaction condition is consistent and is not required to be adjusted, and the metal catalyst is not required to be added into the reaction system, so that impurities such as metal and the like can not be introduced into the system on the one hand, and the separation and purification processes of the product are simple on the other hand, so that the synthesis method is a synthesis method which is simple to operate 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 operation convenience and safety can be ensured.
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FIG. 1 is a diagram showing the mechanism of the synthesis reaction of the α -pyrone compound of the present invention.
Detailed Description
In order that those skilled in the art will better understand the present invention, a technical solution in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in which it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the present invention without making any inventive effort, shall fall within the scope of the present invention.
It should be noted that the terms "comprises" and "comprising," along with any variations thereof, in the description and claims of the present invention are intended to cover a non-exclusive inclusion, such as 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 or inherent to such process, method, article, or apparatus, 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 attached drawing figures:
the invention discloses a synthesis method of an alpha-pyrone compound, which comprises the step of catalyzing bromoacetophenone and cyclopropanone to generate [3+3] cyclization reaction under alkaline heating condition through DMAP to generate the alpha-pyrone compound.
The mechanism of the [3+3] cyclization reaction is that bromoacetophenone and DMAP react to generate an intermediate A, KOH is removed from hydrogen at a carbonyl alpha-position to generate a nitrogenous ylide B, the intermediate B and the intermediate C are tautomerized, an intermediate D is generated by attacking the side of cyclopropenone with smaller steric hindrance, and the ketene structure E generated by leaving DMAP is subjected to the [3+3] cyclization reaction to generate the final product alpha-pyrone. The reaction mechanism is shown in FIG. 1.
Bromoacetophenone and cyclopropenone occur under alkaline heating conditions, and the reaction formula is as follows:
r in the above reaction formula 1 ,R 2 ,R 3 The group is alkyl and aryl;
the method comprises the following steps: adding bromoacetophenone and cyclopropenone into an alkaline organic solvent under the protection of nitrogen, and stirring for 12 hours under the catalysis of DMAP under the heating condition; after the reaction is finished, cooling to room temperature; filtering, rotary evaporation concentration and column chromatography to obtain alpha-pyrone compounds;
preferably, the ratio of cyclopropenone A to bromoacetophenone B in the process of the present invention is 1:1.5; the solvent adopted in the invention is 1, 4-dioxane; the molar 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 is 60 ℃;
example 1
Diphenylcyclopropenone (0.2 mmol), 2-bromo-1-4- (trifluoromethoxy) phenylethanone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol) were added to 100mg of 4A molecular sieve (for the purpose of water removal, the reaction was controlled to proceed under anhydrous conditions) and 1, 4-dioxane (2.0 mL) under nitrogen, heated at 60℃for 12h, cooled to room temperature after completion of the reaction, filtered and concentrated by vacuum distillation and purified by flash column chromatography (silica gel, petroleum ether/ethyl acetate mixture, 20:1, v/v) to afford the desired pure product 67.3mg in 82% yield as a yellow solid with a melting point of 134-136 ℃. The structural formula is as follows:
1 H NMR(400MHz,CDCl 3 )(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).
13 C{1H}NMR(400MHz,CDCl 3 ；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.
IRν max (neat):1697,1504，1266,1210,1150,833,,789，769,699cm -1 .
HRMS(ESI)calcd for C 24 H 15 F 3 O 3 [M+H]+:409.1046,found:409.1048.
example 2
The procedure described in example 1 was followed, except that the substrates used were: diphenylcyclopropenone (0.2 mmol), 2-bromo-1-4- (trifluoromethyl) phenylethanone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0 mL) gave 59.5mg of product in 76% yield as a yellow solid with a melting point of 170-172 ℃. The structural formula is as follows:
1 H NMR(400MHz,CDCl 3 )(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).
13 C{1H}NMR(400MHz,CDCl 3 ；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.
IRν max (neat):1697,1537，1329,1160,1117,1072,831,789,699cm -1 .
HRMS(ESI)calcd for C 24 H 15 F 3 O 2 [M+H]+:393.1097,found:393.1100
example 3
The procedure described in example 1 was followed, except that the substrates used were: diphenylcyclopropenone (0.2 mmol), 2-bromo-1-cyclohexylethanone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol), heating to 65℃and 100mg of 4A molecular sieve and 1, 4-dioxane (2.0 mL) gave 27.8mg of the product as a white solid with a yield of 42% and a melting point of 124-125 ℃. The structural formula is as follows:
1 H NMR(400MHz,CDCl 3 )(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,CH 2 ),1.86(d,J＝12.9Hz,2H,CH 2 ),1.75(d,J＝15.2Hz,1H,CH 2 ),1.57–1.18(m,5H,CH 2 ).
13 C{1H}NMR(400MHz,CDCl 3 ；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.
IRν max (neat):2929,2853，1699,1634,1538,944,764,606,564cm -1 .
HRMS(ESI)calcd for C 23 H 22 O 2 [M+H]+:331.1693,found:331.1690.
example 4
The procedure described in example 1 was followed, except that the substrates used were: 2-butyl-3-phenylcyclopropanone (0.2 mmol), bromoacetophenone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0 mL) were heated to 55℃to give 26.8mg of the product as a yellow solid in 44% yield with a melting point of 92-94 ℃. The structural formula is as follows:
1 H NMR(400MHz,CDCl 3 )(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,CH 2 ),1.51-1.55(m,2H,CH2),1.31–1.24(m,2H,CH 2 ),0.83(t,J＝7.3Hz,3H,CH 3 ).
13 C{1H}NMR(400MHz,CDCl 3 ；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.
IRν max (neat):2962,2927,1706,1627,1538,1451,1351,722,692cm -1 .
HRMS(ESI)calcd for C 21 H 20 O 2 [M+H]+:305.1536,found:305.1537
example 5
The procedure described in example 1 was followed, except that the substrates used were: bis- (4-methylphenyl) cyclopropenone (0.2 mmol), bromoacetophenone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol), heating to 50℃and 100mg of 4A molecular sieve and 1, 4-dioxane (2.0 mL) gave 26.2mg of the product as a yellow solid in 50% yield with a melting point of 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 described in example 1 was followed, except that the substrates used were: 2-3-bis (4-methylphenyl) cyclopropenone (0.2 mmol), bromoacetophenone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0 mL) gave 42.2mg of product in 59% yield as a yellow solid with a melting point of 158-160 ℃. The structural formula is as follows:
1 H NMR(400MHz,CDCl 3 )(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,CH 3 ).
13 C{1H}NMR(400MHz,CDCl 3 ；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.
IRν max (neat):1701,1625,1531,1350,979,815,726,690,646cm -1 .
HRMS(ESI)calcd for C 25 H 20 O 2 [M+H]+:353.1536,found:353.1536.
example 7
The procedure described in example 1 was followed, except that the substrates used were: 2-3-bis (4-fluorophenyl) cyclopropanone (0.2 mmol), bromoacetophenone (0.3 mmol), DMAP (20 mol%), KOH (0.3 mmol), 100mg of 4A molecular sieve and 1, 4-dioxane (2.0 mL) give 64.1mg of the product in 89% yield as a yellow solid with a melting point of 204-206 ℃. The structural formula is as follows:
1 H NMR(400MHz,CDCl 3 )(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).
13 C{1H}NMR(400MHz,CDCl 3 ；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.
IRν max (neat):1687,1536,1351,1223,1157,842,762,557,543cm -1 .
HRMS(ESI)calcd for C 23 H 14 F 2 O 2 [M+H]+:361.1035,found:361.1037.
the above is only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited by this, and any modification made on the basis of the technical scheme according to the technical idea of the present invention falls within the protection scope of the claims of the present invention.
Claims (5)
1. The synthesis method of the alpha-pyrone compound is characterized in that 4-dimethylaminopyridine catalyzes alpha-bromoketone and substituted cyclopropanone to perform [3+3] cyclization reaction under alkaline heating condition to synthesize the alpha-pyrone compound, wherein:
the structural formula of the alpha-bromoketone is as follows:
the structural formula of the substituted cyclopropenone is as follows:
the structural formula of the synthesized alpha-pyrone compound is as follows:
wherein R is 1 ,R 2 ,R 3 The group is alkyl or aryl;
the method specifically comprises the following steps:
1) Under the protection of nitrogen, adding alpha-bromoketone and substituted cyclopropanone into an alkaline organic solvent, and under the heating condition, carrying out catalytic stirring on 4-dimethylaminopyridine for 8-14 h, and cooling to room temperature after the reaction is finished; wherein:
the heating temperature is 50-65 ℃;
the organic solvent is 1, 4-dioxane, and is adjusted to be alkaline by adding potassium hydroxide;
2) Filtering, concentrating and purifying the reaction system by column chromatography to obtain the alpha-pyrone compound.
2. The method for synthesizing an alpha-pyrone compound according to claim 1, wherein the reaction molar ratio of the substituted cyclopropenone, the alpha-bromoketone and the 4-dimethylaminopyridine is 1.0:1.0-1.5.
3. The method for synthesizing an α -pyrone compound according to claim 1, wherein the reaction charge ratio of the substituted cyclopropenones to the organic solvent is 0.2mmol (1-2) mL.
4. The method for synthesizing an α -pyrone compound according to claim 1, wherein the heating temperature is 60 ℃.
5. The method for synthesizing an α -pyrone compound according to claim 1, wherein in step 1), column chromatography is performed using a silica gel column using petroleum ether: ethyl acetate = 20: purifying by passing the mixture through a column according to the volume ratio of 1.
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