CN110483379B - Preparation method of 1,2, 2-triaryl ethanone compound - Google Patents
Preparation method of 1,2, 2-triaryl ethanone compound Download PDFInfo
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- CN110483379B CN110483379B CN201910796038.7A CN201910796038A CN110483379B CN 110483379 B CN110483379 B CN 110483379B CN 201910796038 A CN201910796038 A CN 201910796038A CN 110483379 B CN110483379 B CN 110483379B
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
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Abstract
The invention discloses a 1,2, 2-triarylThe preparation method of the ethanone compound comprises the following steps:
wherein Ar is1、Ar2And Ar3Selected from phenyl, various substituted phenyl, naphthyl and aromatic heterocyclic groups; mixing a compound shown in a formula (I), a compound shown in a formula (II) and alkali in an aprotic solvent according to a molar ratio of 1:1: 2-4, reacting, adding water for quenching, filtering, washing, decompressing, evaporating, and separating by column chromatography to obtain a product (III); wherein the reaction temperature is 60-100 ℃, and the reaction time is 12-18 hours. Under the condition of no metal catalysis, the method takes simple and easily-obtained activated amide as a raw material, and can obtain a series of 1,2, 2-triaryl ethanone compounds with representative structures by coupling with simple diarylmethane compounds under an alkaline condition.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a preparation method of a novel 1,2, 2-triaryl ethyl ketone compound.
Background
Alpha-aryl substituted carbonyl compounds, such as 1, 2-diaryl and 1,2, 2-triaryl ethanones, are very important structural units in natural products and also very common structures in medicaments, and are important synthetic intermediates of a plurality of medicaments, such as tamoxifen, oxcarbazepine and droloxifene, clinically applied at present. The main preparation method of the compounds is based on the alpha-position arylation reaction of carbonyl compounds catalyzed by transition metal. In 1997, three subject groups, Buchwald, Hartwig and Miura, published almost the time for palladium-catalyzed alpha-arylation of carbonyl compounds, and subsequently, based on these three important tasks, other relatively inexpensive transition metals including copper, nickel, iron, etc. were successfully used in this catalytic reaction. In these metal-catalyzed coupling reactions, carbonyl compounds first form enol-type intermediates under basic conditions, and then undergo coupling reactions with electrophiles (including haloaromatics, aromatics, and the like) as the desired nucleophile. Despite the great advances made in this field, there are still many disadvantages associated with the alpha-arylation of metal-catalyzed carbonyl compounds, including: 1) the use of expensive and toxic metal catalysts and ligands is necessary; 2) harsh reaction conditions; 3) the substrate range is limited; 4) metal contaminants harmful to the environment are generated.
In short, the 1,2, 2-triaryl ethanone compounds have important skeleton structures with physiological activity and have irreplaceable functions in the field of organic chemical industry. The corresponding synthetic method of the compound has the problems of complicated operation, metal pollution, use of excessive oxidant or other reagents, pretreatment of complex substrates and the like. Therefore, a more environment-friendly, green and efficient synthesis method is developed for the compounds, so that the method not only has very important application value, but also has very important scientific significance in theory.
Disclosure of Invention
The invention provides a preparation method of a 1,2, 2-triaryl ethyl ketone compound, which has the advantages of simple process, no metal catalysis, no additive, no oxidant, high efficiency and environmental protection.
The technical scheme adopted by the invention is as follows: a preparation method of 1,2, 2-triaryl ethanone compounds comprises the following steps: mixing a compound shown in a formula (I), a compound shown in a formula (II) and alkali in an aprotic solvent according to a molar ratio of 1:1: 2-4, reacting, adding water for quenching, filtering, washing, decompressing, evaporating, and separating by column chromatography to obtain a product (III);
wherein Ar is1、Ar2And Ar3Selected from phenyl and various substituted benzenesA phenyl, naphthyl, heteroaromatic group; the reaction temperature is 60-100 ℃, and the reaction time is 12-18 hours.
Further, the aprotic solvent is selected from tetrahydrofuran, ethylene glycol dimethyl ether, cyclopentyl methyl ether and dioxane.
Further, the base is selected from hexamethyldisilazane, sodium hexamethyldisilazane or lithium hexamethyldisilazane.
Further, after quenching, silica gel powder is added for filtration.
Further, washing was performed with ethyl acetate.
Further, in column chromatography separation, the PE: EA is 8: 1-2: 1.
The structure of the 1,2, 2-triaryl ethanone compound obtained by the method is as follows:
compared with the prior art, the invention has the following beneficial effects: under the condition of no metal catalysis, the method takes simple and easily-obtained activated amide as a raw material, and can obtain a series of 1,2, 2-triaryl ethanone compounds with representative structures by coupling with simple diarylmethane compounds under an alkaline condition.
Detailed Description
The present invention will be described in detail below based on preferred embodiments, and objects and effects of the present invention will become more apparent, and the present invention will be further described in detail below based on the 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.
The synthesis method of the 1,2, 2-triaryl ethanone compound comprises the following steps:
wherein Ar is1Selected from phenyl, various substituted phenyl and naphthaleneA group such as a phenyl group, a heteroaryl group, etc.; ar (Ar)2And Ar3The groups such as phenyl, various substituted phenyl, naphthyl, aromatic heterocycle and the like are selected.
Dissolving 0.1mmol of the compound shown in the formula (I) and 0.1mmol of the compound shown in the formula (II) in 2mL of tetrahydrofuran solvent (dimethyl glycol ether, cyclopentyl methyl ether or dioxane can be used for replacing), adding 0.2-0.4mmol of sodium hexamethyldisilazide (potassium hexamethyldisilazide or lithium hexamethyldisilazide) under stirring, reacting for 12-18 hours under the heating condition of 60-100 ℃, adding 3 drops of water for quenching, adding a small amount of silica gel powder for filtering, washing with ethyl acetate, decompressing and evaporating, and separating the mixture by column chromatography (PE: EA is 8: 1-2: 1) to obtain the product (III).
The structure of the 1,2, 2-triaryl ethanone compound obtained by the method is as follows:
example 1
Preparation and characterization of Compound III-1:
under the protection of nitrogen, dissolving a compound I-1 (17.1mg,0.1mmol) and a compound II-2(16.9mg,0.1mmol) in anhydrous tetrahydrofuran (2mL), adding hexamethyldisilazane sodium amide (54.7mg, 0.3mmol) at room temperature (24 ℃), stirring at 80 ℃ for 12 hours, adding 3 drops of water for quenching, adding a small amount of silica gel powder for filtering, washing with ethyl acetate, evaporating to dryness under reduced pressure, and separating the mixture by column chromatography (PE: EA is 10: 1-3: 1) to obtain a product III-1 with the yield of 94%;1H NMR(500MHz,CDCl3)δ:8.55(d,J＝5.4Hz,2H),7.99(m,2H),7.56–7.52(m,1H),7.45–7.40(m,2H),7.38–7.33(m,2H),7.29(m,3H),7.19(d,J＝5.9Hz,2H),6.00(s,1H).
example 2
Preparation and characterization of Compound III-2:
the preparation conditions were the same as in example 1, white solid, yield 80%;1H NMR(500MHz,CDCl3)δ:8.55(t,J＝7.5Hz,2H),8.01–7.97(m,2H),7.57–7.53(m,1H),7.43(dd,J＝10.7,4.9Hz,2H),7.30–7.27(m,1H),7.18(t,J＝5.4Hz,2H),6.88(d,J＝7.7Hz,1H),6.85–6.80(m,2H),5.96(d,J＝5.3Hz,1H),3.77(s,3H).
example 3
Preparation and characterization of Compound III-3:
the preparation was carried out under the same conditions as in example 1, white solid in 81% yield;1H NMR(500MHz,CDCl3)δ:8.54(d,J＝5.9Hz,2H),7.99–7.94(m,2H),7.58–7.54(m,1H),7.46–7.42(m,2H),7.29–7.23(m,2H),7.18–7.14(m,2H),7.04(m,J＝9.6,5.9,2.6Hz,2H),5.98(s,1H).
example 4
Preparation and characterization of Compound III-4:
the preparation conditions were the same as in example 1, white solid, yield 83%;1H NMR(500MHz,CDCl3)δ:8.45(d,J＝5.9Hz,2H),7.92–7.89(m,2H),7.47–7.43(m,1H),7.36–7.32(m,2H),7.28–7.25(m,2H),7.12(m,4H),5.89(s,1H),1.20(s,9H).
example 5
Preparation and characterization of Compound III-5:
preparation conditionsAs in example 1, white solid, 86% yield;1H NMR(500MHz,CDCl3)δ:8.52(d,J＝5.8Hz,2H),8.01–7.96(m,2H),7.56–7.52(m,1H),7.42(dd,J＝10.7,4.9Hz,2H),7.20–7.15(m,6H),5.96(s,1H),2.32(s,3H).
example 6
Preparation and characterization of Compound III-6:
the preparation conditions were the same as in example 1, white solid, yield 80%;1H NMR(500MHz,CDCl3)δ:8.54(dd,J＝4.6,1.5Hz,2H),7.89(m,2H),7.55–7.50(m,1H),7.43–7.38(m,2H),7.25(dd,J＝4.2,3.5Hz,1H),7.21(m,1H),7.15(m,1H),7.11(dd,J＝4.6,1.5Hz,2H),7.07(dd,J＝7.7,1.0Hz,1H),6.08(s,1H),2.35(s,3H).
example 7
Preparation and characterization of Compound III-7:
the preparation conditions were the same as in example 1, white solid, yield 84%;1H NMR(500MHz,CDCl3)δ:8.56(t,J＝7.0Hz,2H),7.99(m,2H),7.56–7.52(m,1H),7.45–7.41(m,2H),7.26–7.20(m,3H),7.13–7.05(m,3H),5.98(s,1H),2.32(s,3H).
example 8
Preparation and characterization of Compound III-8:
the preparation conditions were the same as in example 1, white solid, yield 85%;1H NMR(500MHz,CDCl3)δ:8.55–8.47(m,2H),8.00(m,2H),7.64(m,1H),7.56–7.51(m,1H),7.44–7.40(m,2H),7.36–7.32(m,2H),7.31–7.26(m,4H),6.04(s,1H).
example 9
Preparation and characterization of Compound III-9:
the preparation conditions were the same as in example 1, white solid, yield 68%;1H NMR(500MHz,CDCl3)δ:8.01–7.98(m,2H),7.54–7.50(m,1H),7.42(dd,J＝10.7,4.9Hz,2H),7.38(t,J＝1.8Hz,1H),7.34(m,4H),7.30–7.27(m,1H),6.32(dd,J＝3.2,1.9Hz,1H),6.12(d,J＝3.3Hz,1H),6.03(s,1H).
example 10
Preparation and characterization of Compound III-10:
the preparation conditions were the same as in example 1, white solid, yield 40%;1H NMR(500MHz,CDCl3)δ:8.03–8.00(m,2H),7.55–7.51(m,1H),7.44–7.41(m,2H),7.39(t,J＝1.7Hz,1H),7.35–7.31(m,4H),7.29–7.27(m,1H),7.27–7.25(m,1H),6.37(d,J＝1.0Hz,1H),5.86(s,1H).
example 11
Preparation and characterization of Compound III-11:
the preparation conditions were the same as in example 1, white solid, yield 32%;1H NMR(500MHz,CDCl3)δ:7.99(m,2H),7.57–7.53(m,1H),7.46–7.42(m,2H),7.39(dd,J＝1.8,0.8Hz,1H),7.36–7.30(m,2H),7.04(m,2H),6.33(dd,J＝3.2,1.9Hz,1H),6.13(d,J＝3.3Hz,1H),6.02(s,1H).
example 12
Preparation and characterization of Compound III-12:
the preparation conditions were the same as in example 1, white solid, yield 86%;1H NMR(500MHz,CDCl3)δ:8.07(dd,J＝8.4,1.1Hz,2H),7.58–7.53(m,1H),7.50(d,J＝7.5Hz,1H),7.48–7.44(m,4H),7.43(s,1H),7.42–7.37(m,2H),7.36–7.31(m,1H),7.27–7.23(m,1H),7.20(m,1H),6.53(s,1H),6.19(s,1H).
example 13
Preparation and characterization of Compound III-13:
the preparation was carried out under the same conditions as in example 1, white solid in 81% yield;1H NMR(500MHz,CDCl3)δ:8.53(d,J＝6.0Hz,2H),7.94–7.89(m,2H),7.40–7.34(m,4H),7.33–7.29(m,1H),7.27(t,J＝1.8Hz,1H),7.26(d,J＝1.8Hz,1H),7.19–7.16(m,2H),5.93(s,1H).
example 14
Preparation and characterization of Compound III-14:
the preparation conditions were the same as in example 1, white solid, yield 83%;1H NMR(500MHz,CDCl3)δ:8.57(dd,J＝4.7,1.4Hz,2H),8.52(s,1H),8.04(dd,J＝8.6,1.8Hz,1H),7.91(d,J＝8.1Hz,1H),7.86(t,J＝8.7Hz,2H),7.61–7.58(m,1H),7.55–7.52(m,1H),7.39–7.34(m,4H),7.29(m,1H),7.25(dd,J＝4.7,1.4Hz,2H),6.18(s,1H).
example 15
Preparation and characterization of Compound III-15:
the preparation conditions were the same as in example 1, white solid, yield 86%;1H NMR(500MHz,CDCl3)δ:8.56(dd,J＝4.5,1.6Hz,2H),8.09–8.03(m,2H),7.67–7.64(m,2H),7.59(m,2H),7.48–7.44(m,2H),7.42–7.35(m,3H),7.34–7.29(m,3H),7.21(dd,J＝4.7,1.6Hz,2H),6.04(s,1H).
example 16
Preparation and characterization of Compound III-16:
the preparation conditions were the same as in example 1, white solid, yield 86%;1H NMR(500MHz,CDCl3)δ:8.52(d,J＝4.9Hz,2H),7.91–7.87(m,2H),7.36–7.32(m,2H),7.30–7.26(m,3H),7.21(d,J＝8.2Hz,2H),7.18(dd,J＝4.6,1.5Hz,2H),5.99(s,1H),2.37(s,3H).
example 17
Preparation and characterization of Compound III-17:
the preparation conditions were the same as in example 1, white solid, yield 84%;1H NMR(500MHz,CDCl3)δ:8.53(dd,J＝4.6,1.5Hz,2H),7.81(d,J＝5.6Hz,1H),7.77(d,J＝7.7Hz,1H),7.35(m,4H),7.30–7.28(m,3H),7.18(dd,J＝4.6,1.6Hz,2H),6.00(s,1H),2.37(s,3H).
example 18
Preparation and characterization of Compound III-18:
the preparation conditions were the same as in example 1, white solid, yield 73%;1H NMR(500MHz,CDCl3)δ:8.51(dd,J＝4.6,1.4Hz,2H),7.94–7.87(m,2H),7.36–7.24(m,5H),7.19(dd,J＝4.7,1.4Hz,2H),6.63–6.58(m,2H),5.95(s,1H),3.04(s,6H).
example 19
Preparation and characterization of Compounds III-19:
the preparation conditions were the same as in example 1, white solid, yield 76%;1H NMR(500MHz,CDCl3)δ:8.53(dd,J＝4.7,1.4Hz,2H),8.00–7.93(m,2H),7.35(m,2H),7.30–7.27(m,3H),7.17(dd,J＝4.7,1.4Hz,2H),6.91–6.88(m,2H),5.95(s,1H),3.84(s,3H).
example 20
Preparation and characterization of Compound III-20:
the preparation conditions were the same as in example 1, white solid, yield 40%;1H NMR(500MHz,CDCl3)δ:8.51(dd,J＝4.5,1.6Hz,2H),7.64(dd,J＝7.7,1.8Hz,1H),7.42(m,1H),7.33–7.22(m,5H),7.20(dd,J＝4.6,1.5Hz,2H),6.96(m,1H),6.89(d,J＝8.2Hz,1H),6.11(s,1H),3.80(s,3H).
the above description is only a preferred embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes, which are made by the present specification, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (5)
1. A preparation method of 1,2, 2-triaryl ethanone compounds is characterized by comprising the following steps: mixing a compound shown in a formula (I), a compound shown in a formula (II) and alkali in an aprotic solvent according to a molar ratio of 1:1: 2-4, reacting, adding water for quenching, filtering, washing, decompressing, evaporating, and separating by column chromatography to obtain a product (III);
wherein Ar is1、Ar2And Ar3Selected from phenyl, various substituted phenyl, naphthyl and aromatic heterocyclic groups; the reaction temperature is 60-100 ℃, and the reaction time is 12-18 hours;
the base is selected from hexamethyldisilazane, sodium hexamethyldisilazane or lithium hexamethyldisilazane.
2. The method according to claim 1, wherein the aprotic solvent is selected from tetrahydrofuran, ethylene glycol dimethyl ether, cyclopentyl methyl ether, and dioxane.
3. The method according to claim 1, wherein the quenching is followed by filtration by adding silica gel powder.
4. The method according to claim 1, wherein the washing is performed with ethyl acetate.
5. The preparation method of claim 1, wherein the petroleum ether-ethyl acetate = 8: 1-2: 1 in the column chromatography separation.
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