CN108484552B - Polysubstituted 3-benzofuranone spirocyclohexene derivative and preparation method thereof - Google Patents
Polysubstituted 3-benzofuranone spirocyclohexene derivative and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a polysubstituted 3-benzofuranone spirocyclohexene derivative and a preparation method thereof, wherein the structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative is shown as a formula I:
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a polysubstituted 3-benzofuranone spirocyclohexene derivative and a preparation method thereof.
Background
The 3-benzofuranone spiro-compound is widely available in the nature, and especially widely applied to the aspects of medicines, pesticides and the like. The 3-benzofuranone spirocyclohexene derivative is closely related to life of people, and a 3-benzofuranone spirocyclohexene structural framework exists in a plurality of natural products and medicines, such as: natural product leptosphaerin c with antibacterial activity separated from marine fungus, antifungal antibiotic Griseofulvin, etc. Based on the importance of 3-benzofuranone spiro compounds in medicines and pesticides, chemists develop various methods for constructing the compounds, but the preparation methods of the 3-benzofuranone spiro compounds reported in the literature mainly focus on constructing compounds such as 3-benzofuranone spirocyclopentane, 3-benzofuranone spiropentaheterocycle, 3-benzofuranone spirohexane and the like, but the obtained 3-benzofuranone spirocyclic compounds have limited types, and the reports of 3-benzofuranone spirohexene derivatives, especially multi-substituted 3-benzofuranone spirohexene derivatives, which are widely present in natural products are few and limited. Therefore, the polysubstituted 3-benzofuranone spirocyclohexene derivative with various types and novel structure is developed by efficiently constructing and preparing the polysubstituted 3-benzofuranone spirocyclohexene derivative with a specific structure through one-pot reaction, so that the polysubstituted 3-benzofuranone spirocyclohexene derivative has important significance for the development of medicinal chemistry.
The one-pot multi-component reaction mixes the reactants together, and a series of multi-step reactions occur in one vessel, so that the organic preparation reaction is efficient, and a chemical structure with larger complexity can be obtained by using few steps. Compared with the traditional chemical reaction, the one-pot multi-component reaction is carried out in one container, the separation step of an intermediate is omitted, the time can be obviously saved, the yield is improved, the one-pot reaction is the best way for all organic synthesis routes, and the method has the advantages of high efficiency, convenience, atom economy, low cost and the like. Simpler raw materials can be conveniently converted into complex molecules through one-pot multi-component reaction. In particular, in the preparation of complex structures and natural products, one-pot multicomponent reactions can often play a very critical role, and therefore, in recent years, have attracted increasing attention.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a polysubstituted 3-benzofuranone spirocyclohexene derivative and a preparation method thereof.
In order to solve the technical problems, the invention adopts the following technical scheme:
a polysubstituted 3-benzofuranone spirocyclohexene derivative has a structural formula shown in formula I:
wherein R is1Is selected from the group consisting of: CN or CO2Me；
Wherein R is2The structural formula of (A) is selected from one of the following structural formulas:
wherein R is3The structural formula of (A) is selected from one of hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amino, amido, alkanoyloxy, cyano, aryl, alkenyl, halogenated benzyloxy, halogenated benzylamino or halogenated phenoxy;
the R is1＇、R2Each independently selected from one of hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amino, amido, alkanoyloxy, cyano, aryl, alkenyl, halobenzyloxy, halobenzylamino, or halophenoxy;
the alkyl is C1-C18 straight chain or branched chain alkyl, carbocycle or heterocycle (containing 1-3 oxygen, sulfur or nitrogen), substituted or unsubstituted alkyl, wherein the substituent is halogen, hydroxyl, carboxyl, nitro, cyano, substituted amino, amido, carboxyl, ester group, alkoxy, alkylamino alkanoyloxy and aryl;
the aryl is substituted or unsubstituted aromatic ring or substituted or unsubstituted aromatic heterocycle;
the aromatic ring is a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, an isoquinoline ring, a pyrrole ring, a pyridine ring, a pyrimidine ring, a furan ring or a thiophene ring; the substituent is halogen, methyl, trifluoromethyl, hydroxyl, nitro, amino, substituted amino, carboxyl, ester group, alkoxy, alkanoyloxy or cyano.
The preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: benzaldehyde, malononitrile and 3-benzofuranone react for 1 to 72 hours under the conditions that potassium carbonate is used as a catalyst, dichloromethane is used as a solvent and the temperature is 20 to 80 ℃, and the polysubstituted 3-benzofuranone spirocyclohexene derivative is prepared by column chromatography separation.
The mass ratio of the benzaldehyde to the malononitrile to the 3-benzofuranone is 2:2:1 to 3:3: 1.
The amount of the substance of potassium carbonate is 10-80% of the amount of the substance of 3-benzofuranone based on the amount of the substance of 3-benzofuranone.
The reaction temperature is preferably 30 to 60 ℃.
And eluting petroleum ether and ethyl acetate for column chromatography, wherein the volume ratio of the petroleum ether to the ethyl acetate is 15:1 to 1: 1.
The invention has the beneficial effects that: the invention provides a simple, efficient and convenient preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative, which is characterized in that the polysubstituted 3-benzofuranone spirocyclohexene derivative is prepared by taking potassium carbonate as a catalyst and dichloromethane as a solvent, and has the advantages of high efficiency, convenience, low cost and the like, and the application prospect is good.
Detailed Description
The present invention will be further described with reference to the following examples. It is to be understood that the following examples are illustrative only and are not intended to limit the scope of the invention, which is to be given numerous insubstantial modifications and adaptations by those skilled in the art based on the teachings set forth above.
Example 1
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the turbo-phthalazine derivative of the embodiment comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 31.8mg (0.3mmol) of benzaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 2 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
Example 2
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 45.3mg (0.3mmol) of 4-nitrobenzaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 5 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
1H NMR(400MHz,CDCl3)δ7.51–7.35(m,4H),7.31–7.23(m,2H),7.23-7.03(m,7H),6.79(t,J＝7.4Hz,1H),5.22(s,2H),4.34(s,1H),3.98(s,1H).
Example 3
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 37.2mg (0.3mmol) of 4-fluorobenzaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 72 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
1H NMR(400MHz,DMSO)δ7.71–7.56(m,3H),7.40(dd,J＝8.8,5.3Hz,2H),7.21(d,J＝8.4Hz,1H),7.17(d,J＝7.7Hz,1H),7.11(t,J＝8.4Hz,2H),6.91(t,J＝7.4Hz,3H),4.98(s,1H),4.41(s,1H),3.40(s,2H).
Example 4
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 40.5mg (0.3mmol) of 4-methoxybenzaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 72 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
1H NMR(400MHz,CDCl3)δ7.49–7.43(m,1H),7.31(d,J＝9.0Hz,2H),7.23–6.97(m,4H),6.94(s,1H),6.81(t,J＝7.4Hz,1H),6.67(t,J＝8.9Hz,3H),5.13(s,2H),4.27(s,1H),3.91(s,1H),3.69(s,3H),3.63(s,3H).
Example 5
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 55.5mg (0.3mmol) of 4-bromobenzaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 72 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate in a volume ratio of 15: 1-1: 1).
1H NMR(400MHz,CDCl3)δ7.73(dd,J＝8.0,1.7Hz,1H),7.65(dd,J＝8.1,1.4Hz,1H),7.51–7.47(m,1H),7.33–7.28(m,1H),7.19–7.12(m,3H),7.06–6.96(m,2H),6.85(t,J＝7.4Hz,1H),6.77(tt,J＝7.4,1.2Hz,1H),6.70(d,J＝7.6Hz,1H),5.22(s,2H),5.20(s,1H),5.10(s,1H).
Example 6
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 46.9mg (0.3mmol) of 4-bromobenzaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 72 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate in a volume ratio of 15: 1-1: 1).
isomer A:isomer B＝1:0.24.1H NMR(400MHz,CDCl3)δ8.46(d,J＝9.1Hz,1H,forisomer B),8.37(d,J＝8.7Hz,1H,for isomer A),8.31(d,J＝8.7Hz,1H,for isomer B),8.02–7.93(m,2H,for isomer A and isomer B),7.83(d,J＝8.2Hz,1H,for isomer A andisomer B),7.79–7.52(m,8H,isomer A and isomer B),7.43–7.30(m,4H,for isomer Aand isomer B),7.22–7.06(m,2H,for isomer A and isomer B),7.03(d,J＝8.4Hz,1H,for isomer A),6.90(d,J＝7.0Hz,1H,for isomer B),6.70(d,J＝7.7Hz,1H,for isomerB),6.65(d,J＝7.7Hz,1H,for isomer A),6.62–6.47(m,1H,for isomer A and isomerB),5.54(s,1H,for isomer A),5.32(s,1H,for isomer A),5.29(s,1H,for isomer B),5.24(s,1H,for isomer B),5.18(s,2H,for isomer B),5.16(s,2H,for isomer A).
Example 7
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 46.9mg (0.3mmol) of 1-naphthaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 48 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
1H NMR(400MHz,CDCl3)δ8.24(d,J＝17.0Hz,1H),8.03(dd,J＝8.2,1.3Hz,1H),7.86–7.60(m,3H),7.40(d,J＝7.1Hz,1H),7.29(t,J＝8.0Hz,2H),7.04(dd,J＝43.6,14.1Hz,3H),6.77(t,J＝7.5Hz,1H),6.57(d,J＝14.1Hz,2H),4.68(d,J＝6.4Hz,1H),4.41(d,J＝5.0Hz,1H),3.85(s,3H),3.31(s,3H).
Example 8
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 42.2mg (0.3mmol) of 4-chloroformaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 72 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
1H NMR(400MHz,CDCl3)δ7.44–7.38(m,1H),7.26(d,J＝8.6Hz,2H),7.15(dd,J＝12.3,7.7Hz,2H),7.05(d,J＝8.7Hz,3H),6.94(d,J＝8.4Hz,1H),6.81(dd,J＝16.4,8.8Hz,3H),6.34(s,2H),4.53(s,1H),4.21(s,1H),3.79(s,3H),3.31(s,3H).
Example 9
The structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative of the present example is as follows:
the preparation method of the polysubstituted 3-benzofuranone spirocyclohexene derivative comprises the following steps: adding 20.1mg (0.15mmol) of 3-benzofuranone, 42.2mg (0.3mmol) of 2-thiophenecarboxaldehyde, 19.8mg (0.3mmol) of malononitrile, 8.3mg (40% eq) of potassium carbonate and 1mL of dichloromethane into a reaction test tube, stirring and reacting for 72 hours at the temperature of 20-80 ℃, and separating by column chromatography to obtain a target product (eluent: petroleum ether and ethyl acetate volume ratio is 15: 1-1: 1).
1H NMR(400MHz,CDCl3)δ7.75(dd,J＝8.1,1.7Hz,1H),7.45–7.40(m,2H),7.16–7.12(m,1H),6.92-6.99(m,5H),5.25(s,2H),5.18(s,1H),5.10(s,1H).
The foregoing shows and describes the general principles and features of the present invention, together with the advantages thereof. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (5)
1. A preparation method of polysubstituted 3-benzofuranone spirocyclohexene derivatives is characterized by comprising the following steps: benzaldehyde, malononitrile and multi-substituted 3-benzofuranone react for 1 to 72 hours under the conditions that potassium carbonate is used as a catalyst and dichloromethane is used as a solvent at the temperature of between 20 and 80 ℃, and the multi-substituted 3-benzofuranone spirocyclohexene derivative is prepared by column chromatography separation; the structural formula of the polysubstituted 3-benzofuranone spirocyclohexene derivative is shown as a formula I:
（Ⅰ）
wherein R is1Selected from: CN or CO2Me； R2One selected from the following structural formulas:
R3one selected from hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amido, alkanoyloxy, cyano, aryl, alkenyl, halogenated benzyloxy, halogenated benzylamino or halogenated phenoxy;
the R is1＇、R2Each independently selected from one of hydrogen, halogen, alkyl, trifluoromethyl, hydroxyl, alkoxy, nitro, ester group, amino, amido, alkanoyloxy, cyano, aryl, alkenyl, halobenzyloxy, halobenzylamino, or halophenoxy;
the alkyl is C1-C18 straight chain or branched chain alkyl, carbocycle or heterocycle, substituted or unsubstituted alkyl, wherein the substituent is halogen, hydroxyl, carboxyl, nitro, cyano, substituted amino, amido, carboxyl, ester group, alkoxy, alkylamino alkanoyloxy and aryl;
the aryl is substituted or unsubstituted aromatic ring or substituted or unsubstituted aromatic heterocycle;
the aromatic ring is a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, an isoquinoline ring, a pyrrole ring, a pyridine ring, a pyrimidine ring, a furan ring or a thiophene ring; the substituent is halogen, methyl, trifluoromethyl, hydroxyl, nitro, amino, substituted amino, carboxyl, ester group, alkoxy, alkanoyloxy or cyano.
2. The method for producing a polysubstituted 3-benzofuranone spirocyclohexene derivative according to claim 1, wherein: the mass ratio of the benzaldehyde to the malononitrile to the polysubstituted 3-benzofuranone is 2:2:1 to 3:3: 1.
3. The method for producing a polysubstituted 3-benzofuranone spirocyclohexene derivative according to claim 1, wherein: the amount of the substance of the potassium carbonate is 10 to 80 percent of the amount of the substance of the polysubstituted 3-benzofuranone based on the amount of the substance of the polysubstituted 3-benzofuranone.
4. The method for producing a polysubstituted 3-benzofuranone spirocyclohexene derivative according to claim 1, wherein: the reaction temperature is 30-60 ℃.
5. The method for producing a polysubstituted 3-benzofuranone spirocyclohexene derivative according to claim 1, wherein: and eluting petroleum ether and ethyl acetate for column chromatography, wherein the volume ratio of the petroleum ether to the ethyl acetate is 15:1 to 1: 1.
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