CN108503578B - Synthetic method of indeno- [1,2-b ] indole-10 (5H) -ketone compound - Google Patents
Synthetic method of indeno- [1,2-b ] indole-10 (5H) -ketone compound Download PDFInfo
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Abstract
The invention relates to a synthetic method of indeno- [1,2-b ] indole-10 (5H) -ketone compounds. The synthesis method comprises the following steps: reacting the 3- (2-bromobenzoyl) -indole compound shown in the formula (1) with an alkyl lithium reagent, zinc halide and lithium halide to generate an indole zinc reagent shown in the formula (2), and then carrying out intramolecular coupling reaction to generate a target product. The synthesis method has the advantages that 3- (2-bromobenzoyl) -indole compounds react with alkyl lithium reagents, zinc halide and lithium halide, the exchange of halogen lithium is avoided through the selection of a substrate structure and a reaction reagent, the indole zinc reagent is generated on site, the coupling reaction is further carried out, and the indeno- [1,2-b ] indole-10 (5H) -ketone structure is efficiently constructed. The method avoids the use of expensive transition metal catalysts, has low cost and simple operation, and is convenient for large-scale industrial production.
Description
Technical Field
The invention belongs to the field of preparation of nitrogen-containing heterocyclic compounds, and particularly relates to a synthesis method of indeno- [1,2-b ] indole-10 (5H) -ketone compounds.
Background
The cyclic indole and the derivatives thereof are important nitrogen-containing heterocyclic compounds which widely exist in nature and are currently applied to the fields of medicines, dyes, fine chemical engineering and the like. For example, indole compounds having a tricyclic, tetracyclic skeleton are direct precursors to the synthesis of antihistamines and anti-inflammatory drugs. Recent research shows that indeno- [1,2-b ] indole-10 (5H) -ketone compounds have remarkable pharmacological activities such as anticancer, anti-senile dementia, antioxidation and the like, and are also ligands of human protein kinase CK2 inhibitors and MT3 melatonin binding sites, so that the synthesis of the compounds also arouses the wide research interest of chemists.
The patent application with publication number CN106349150A discloses a synthesis method of indeno- [1,2-b ] indole-10 (5H) -ketone compounds, which takes N-substituted-2- (2-bromoaryl) -1H-indole compounds and CO as starting materials, palladium acetate as a catalyst, DABCO as an alkali, N-butyl di (1-adamantyl) phosphine as a ligand and dimethyl sulfoxide or N-methylpyrrolidone as a solvent, and the target products are prepared by heating and stirring the materials in a reaction vessel at 120 ℃.
In the existing method, expensive palladium catalyst is used in the reaction, about 15-30% of diamantanyl n-butylphosphine organic ligand with special structure is added, and toxic carbon monoxide gas is used, which not only increases the cost, but also brings inconvenience to the reaction operation and the separation and purification of the product.
Disclosure of Invention
The invention aims to provide a method for synthesizing indeno- [1,2-b ] indole-10 (5H) -ketone compounds, so as to solve the problems of high synthesis cost and complicated reaction operation in the existing method.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a synthetic method of indeno- [1,2-b ] indole-10 (5H) -ketone compounds comprises the following steps: reacting the 3- (2-bromobenzoyl) -indole compound shown in the formula (1) with an alkyl lithium reagent, zinc halide and lithium halide to generate an indole zinc reagent shown in the formula (2), and then carrying out intramolecular coupling reaction to generate a target product;
in the formulae (1) and (2), R1Is an alkyl group; r2Is H, alkyl, alkoxy, halogen, cyano, nitro, ester group, acyl, aryl or substituted aryl, wherein the substituent is alkyl, alkoxy or halogen, R3Is H, alkyl, alkoxy, halogen, cyano, nitro, ester group, acyl and aryl, and X is halogen.
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound provided by the invention has the advantages that the 3- (2-bromobenzoyl) -indole compound reacts with an alkyl lithium reagent, zinc halide and lithium halide, the halogen lithium exchange is avoided through the selection of a substrate structure and a reaction reagent, the indole zinc reagent is generated on site, the coupling reaction is further carried out, and the indeno- [1,2-b ] indole-10 (5H) -ketone structure is efficiently constructed. The method avoids the use of expensive transition metal catalysts, has low cost and simple operation, and is convenient for large-scale industrial production.
In the formulae (1) and (2), R1Preferably C1-C8 alkyl, more preferably C1-C6 alkyl. R2Preferably alkyl, alkoxy, halogen, aryl, more preferably C1-C6 alkyl, C1-C6 alkoxy, halogen, phenyl. R3Preferably alkyl, alkoxy, halogen, more preferably C1-C6 alkyl, C1-C6 alkoxy, halogen.
From the viewpoint of reagent cost and reaction effect, the alkyllithium reagent is preferably n-butyllithium and/or t-butyllithium, and more preferably n-butyllithium. The zinc halide is at least one of zinc bromide, zinc chloride and zinc iodide, and is more preferably zinc iodide. The lithium halide is at least one of lithium bromide, lithium chloride and lithium iodide, and is more preferably lithium iodide.
In order to promote the reaction raw material represented by the formula (1) to be sufficiently converted and to improve the reaction yield, it is preferable that the molar ratio of the compound represented by the formula (1), the alkyllithium reagent, the zinc halide and the lithium halide is 1: (1.0-1.2): (1.0-1.2): (1.5-3.0), and more preferably, the molar ratio of the above components is 1:1.05:1.05: 2.5.
In order to promote the reaction to be smoothly and orderly carried out, reduce the occurrence of side reactions and improve the reaction efficiency, the reaction of the 3- (2-bromobenzoyl) -indole compound shown in the formula (1) and an alkyl lithium reagent, zinc halide and lithium halide is preferably carried out in an ether solvent, and further preferably, after the indole zinc reagent shown in the formula (2) is generated, an aromatic hydrocarbon solvent is added into the system, and then the intramolecular coupling reaction is carried out, more preferably, the concentration of the 3- (2-bromobenzoyl) -indole compound shown in the formula (1) in the ether solvent is 0.1-0.5 mol/L, the volume ratio of the aromatic hydrocarbon solvent to the ether solvent is (1-20): 1, most preferably, (1-5): 1, the ether solvent can be tetrahydrofuran, diethyl ether and the like, and the aromatic hydrocarbon solvent can be toluene, xylene and the like.
The reaction temperature of the 3- (2-bromobenzoyl) -indole compound shown in the formula (1), the alkyllithium reagent, the zinc halide and the lithium halide is-80 to-60 ℃, and is preferably-78 ℃. The reaction speed of the step is high, and the reaction can be returned to room temperature after reaction and stirred for a certain time, so that the reaction system is stable and the reaction is further promoted to be complete, thereby preparing for the subsequent intramolecular coupling reaction. Preferably, the reaction temperature of the intramolecular coupling reaction is 90-130 ℃, and the reaction time is 12-48 h. Further preferably, the reaction temperature of the intramolecular coupling reaction is 110 ℃, and the reaction time is 24 h.
The reaction for generating the indole zinc reagent shown as the formula (2) and the intramolecular coupling reaction are carried out under the protective atmosphere, protective gases such as nitrogen, argon and the like can be introduced in industrial production, and a Schlenk reaction tube can be adopted in laboratory preparation.
After intramolecular coupling reaction, adding an organic solvent for extraction, drying an organic phase, removing the organic solvent, and separating by using column chromatography to obtain a target product. The organic solvent for extraction is preferably diethyl ether. The eluent used for column chromatography analysis consists of petroleum ether and ethyl acetate, and the preferred volume ratio of the petroleum ether to the ethyl acetate is (4-6): 1. compared with the existing synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound, the synthetic method has the advantages of simple post-treatment steps, convenience for separation and purification, high product yield and suitability for industrial production of target products.
Detailed Description
The following examples are provided to further illustrate the practice of the invention.
In the following examples, the synthetic routes for indeno- [1,2-b ] indol-10 (5H) -ones are as follows:
the reaction characteristics of the synthesis route are as follows: through the selection of a substrate structure and a reaction reagent, the exchange of halogen and lithium is avoided, an indole zinc reagent is generated on site, then a coupling reaction is carried out, and the indeno- [1,2-b ] indole-10 (5H) -ketone structure is efficiently constructed.
Example 1
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
the method comprises the following specific steps:
1a 157.0mg (0.2mmol) and Tetrahydrofuran (THF)0.3m L were added to an oven-dried Schlenk reaction tube, and n-Bu L i in n-hexane (n-hexane) 0.13m L (0.21mmol, 1.6 mol/L), ZnI were added dropwise at-78 deg.C20.13m L (0.21mmol, 1.0 mol/L) in THF and 0.5m L (0.5mmol, 1.0 mol/L) in L iI in THF, stirring at room temperature for 30min, adding toluene (tolumen) 1.86m L, heating to 110 deg.C, reacting for 24 hr, reacting with saturated NH4Cl solution 2m L quenched with diethyl ether (Et)2O, 3 × 10m L), the organic phases are combined, dried by anhydrous sodium sulfate, the solvent is removed by rotary evaporation under reduced pressure, and the compound 2a is obtained by silica gel column chromatography (the eluent is a mixed solvent of petroleum ether and ethyl acetate according to the volume ratio of 5: 1), and the yield is 88%.
The product 5-methylindeno- [1,2-b ] indol-10 (5H) -one (2a) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):3.90(s,3H),7.15-7.26(m,6H),7.40(d,J＝6.8Hz,1H),7.79(d,J＝7.0Hz,1H)；
13C NMR(100MHz,CDCl3):31.5,110.5,114.8,118.3,120.6,122.8,122.9,123.2,123.5,129.5,131.8,134.6,141.2,142.9,158.7,184.9。
example 2
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
referring to example 1, the equimolar amount of 1a in example 1 was replaced by the raw material 1b, and the product was compound 2b, which is 84% yield.
The product 5, 6-dimethylindeno- [1,2-b ] indol-10 (5H) -one (2b) is a red solid, and the product is identified as follows:
1H NMR(400MHz，CDCl3):2.53(s,3H),3.85(s,3H),6.73(d,J＝7.0Hz,1H),6.95-7.13(m,4H),7.24(d,J＝6.6Hz,1H),7.52(d,J＝7.2Hz,1H)；
13C NMR(100MHz,CDCl3):19.3,35.2,114.5,118.3,122.6,123.5,123.7,126.1,128.8,129.2,130.9,131.7,134.7,141.1,141.8,158.7,184.9。
example 3
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1c, and other reaction conditions and specific operation were carried out with reference to example 1, to obtain compound 2c in 90% yield.
5, 7-Dimethylindeno- [1,2-b ] indol-10 (5H) -one (2c) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):2.69(s,3H),3.88(s,3H),6.87-6.92(m,2H),7.00-7.13(m,4H),7.27(d,J＝7.0Hz,1H)；
13C NMR(100MHz,CDCl3):20.1,31.7,107.6,115.3,118.3,122.8,123.4,123.8,124.0,129.3,131.7,134.5,141.0,142.8,158.4,184.5.
example 4
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1d, and other reaction conditions and specific operation were carried out with reference to example 1 to obtain compound 2d in 80% yield.
8-chloro-5-methylindeno- [1,2-b ] indol-10 (5H) -one (2d) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):3.83(s,3H),7.05(s,2H),7.13-7.20(m,2H),7.27(d,J＝7.0Hz,1H),7.40(d,J＝6.8Hz,1H),7.65(s,1H)；
13C NMR(100MHz,CDCl3):31.9,111.4,114.2,118.6,120.2,123.2,123.4,123.6,129.5,130.0,132.0,134.9,140.9,141.3,159.5,184.5.
example 5
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1e, and other reaction conditions and specific operation were carried out with reference to example 1, to obtain compound 2e in 83% yield.
8-bromo-5-methylindeno- [1,2-b ] indol-10 (5H) -one (2e) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):3.86(s,3H),7.05(d,J＝7.9Hz,1H),7.15-7.25(m,4H),7.39(d,J＝6.8Hz,1H),7.80(s,1H)；
13C NMR(100MHz,CDCl3):31.8,111.8,114.2,117.2,118.6,123.3,123.4,124.1,125.9,129.9,132.1,134.4,140.9,141.5,159.3,184.5.
example 6
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1f, and other reaction conditions and specific operation were carried out with reference to example 1, to obtain compound 2f in 77% yield.
5-methyl 8-phenylindeno- [1,2-b ] indol-10 (5H) -one (2f) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):3.93(s,3H),7.20–7.33(m,5H),7.44–7.48(m,4H),7.60–7.64(m,2H),7.99(m,1H)；
13C NMR(100MHz,CDCl3):31.8,110.7,118.3,119.2,122.6,123.2,123.3,125.7,127.0,127.4,128.7,129.7,131.9,137.0,141.3,159.3,184.9.
example 7
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1g, and other reaction conditions and specific operation were carried out with reference to example 1, to obtain 2g of the compound in 83% yield.
8-methoxy-5-methylindeno- [1,2-b ] indol-10 (5H) -one (2g) as a red solid, and the product was confirmed as follows:
1H NMR(400MHz，CDCl3):3.85(s,3H),3.89(s,3H),6.76(dd,J＝8.5,3.8Hz,1H),7.09(d,J＝8.5Hz,1H),7.15–7.19(m,2H),7.21–7.23(m,2H),7.41–7.43(m,1H)；
13C NMR(100MHz,CDCl3):31.9,55.8,102.3,111.2,113.0,114.6,118.1,123.1,123.5,129.5,131.8,134.8,137.9,141.4,157.0,158.4,184.5.
example 8
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1h, and other reaction conditions and specific operation refer to example 1 to obtain compound 2h with 88% yield.
5, 9-Dimethylindeno- [1,2-b ] indol-10 (5H) -one (2H) is a red solid and the product is identified as follows:
1HNMR(400MHz，CDCl3):2.55(s,3H),3.82(s,3H),6.89(s,1H),6.95(d,J＝8.0Hz,1H),7.02(d,J＝7.6Hz,1H),7.10-7.19(m,2H),7.35(d,J＝6.8Hz,1H),7.58(d,J＝8.0Hz,1H)；
13C NMR(100MHz,CDCl3):21.9,31.2,110.6,114.3,118.5,119.7,120.3,122.5,124.7,129.1,131.6,132.8,134.6,141.0,143.1,158.4,184.5.
example 9
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1i, and other reaction conditions and specific operation refer to example 1 to obtain compound 2i in 85% yield.
2, 5-Dimethylindeno- [1,2-b ] indol-10 (5H) -one (2i) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):2.31(s,3H),3.81(s,3H),6.95-7.02(m,2H),7.11-7.22(m,4H),7.69-7.70(m,1H)；
13C NMR(100MHz,CDCl3):20.3,30.7,109.4,113.4,117.2,119.6,121.6,121.8,122.5,123.1,130.5,130.7,138.9,140.5,141.7,158.4,184.9.
example 10
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1j, and other reaction conditions and specific operation refer to example 1 to obtain compound 2j in 85% yield.
3-methoxy-5-methylindeno- [1,2-b ] indol-10 (5H) -one (2j) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):3.72(s,3H),3.77(s,3H),6.45(d,J＝7.8Hz,1H),6.61(s,1H),7.10-7.15(m,3H),7.24(d,J＝8.0Hz,1H),7.69(d,J＝7.2Hz,1H)；
13C NMR(100MHz,CDCl3):31.5,55.6,108.3,109.6,110.4,116.1,120.4,122.6,122.9,123.2,124.3,133.4,136.4,142.7,156.8,162.8,184.2.
example 11
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was substituted by equimolar amount of the starting material 1k, and other reaction conditions and specific operation refer to example 1 to obtain compound 2k in 85% yield.
3, 5-Dimethylindeno- [1,2-b ] indol-10 (5H) -one (2k) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):2.25(s,3H),3.72(s,3H),6.80-6.83(m,2H),7.04-7.11(m,3H),7.20(d,J＝7.2Hz,1H),7.70(d,J＝7.5Hz,1H)；
13C NMR(100MHz,CDCl3):21.7,31.4,110.4,115.1,119.7,120.3,122.7,123.1,129.2,134.8,138.6,142.3,142.7,158.4,184.8.
example 12
The synthetic method of the indeno- [1,2-b ] indole-10 (5H) -ketone compound of the embodiment has the following synthetic route:
1a in example 1 was replaced by equimolar amount of the starting material 1l, and other reaction conditions and specific operation refer to example 1 to obtain 2l of the compound in 73% yield.
3-chloro-5-methylindeno- [1,2-b ] indol-10 (5H) -one (2l) is a red solid and the product is identified as follows:
1H NMR(400MHz，CDCl3):3.83(s,3H),7.05(s,1H),7.08(d,J＝7.6Hz,1H),7.15-7.18(m,3H),7.23-7.25(m,1H),7.68-7.71(m,1H)；
13C NMR(100MHz,CDCl3):31.6,110.6,115.7,118.9,120.7,122.5,123.5,123.6,123.8,128.8,136.3,137.8,139.2,143.0,156.8,183.6.
indeno- [1,2-b]In other examples of methods for the synthesis of indol-10 (5H) -ones, R1、R2、R3When other substituent groups are used, corresponding 3- (2-bromobenzoyl) -indole compounds can be used to replace 1a in the embodiment 1, the types and the dosage of the alkyl lithium reagent, the zinc halide and the lithium halide can be adaptively adjusted within the range defined by the invention, the reaction conditions of the reaction for generating the indole zinc reagent and the intramolecular coupling reaction can be adjusted according to actual conditions, and corresponding substitution type target products can be obtained.
Claims (4)
1. A synthetic method of indeno- [1,2-b ] indole-10 (5H) -ketone compounds is characterized by comprising the following steps: reacting the 3- (2-bromobenzoyl) -indole compound shown in the formula (1) with an alkyl lithium reagent, zinc halide and lithium halide to generate an indole zinc reagent shown in the formula (2), and then carrying out intramolecular coupling reaction to generate a target product;
in the formulae (1) and (2), R1Is methyl; r2Is H, methyl, methoxy, halogen, phenyl, R3Is HMethyl, methoxy, halogen, X is iodine;
the alkyl lithium reagent is n-butyl lithium and/or tert-butyl lithium; the zinc halide is zinc iodide; the lithium halide is lithium iodide;
the reaction of the 3- (2-bromobenzoyl) -indole compound shown in the formula (1) with an alkyl lithium reagent, zinc halide and lithium halide is carried out in an ether solvent, and the reaction temperature is-80 to-60 ℃; the ether solvent is tetrahydrofuran and diethyl ether;
after generating the indole zinc reagent shown in the formula (2), adding an aromatic hydrocarbon solvent into a system, and then carrying out intramolecular coupling reaction, wherein the aromatic hydrocarbon solvent is toluene and xylene; the reaction temperature of the intramolecular coupling reaction is 90-130 ℃.
2. The method for synthesizing indeno- [1,2-b ] indol-10 (5H) -one compounds according to claim 1, wherein the molar ratio of the compound shown in formula (1), the alkyl lithium reagent, the zinc halide and the lithium halide is 1: (1.0-1.2): (1.0-1.2): (1.5-3.0).
3. The method for synthesizing indeno- [1,2-b ] indol-10 (5H) -one compounds according to claim 1, wherein the reaction time of the intramolecular coupling reaction is 12-48H.
4. The method for synthesizing indeno- [1,2-b ] indol-10 (5H) -one compounds according to claim 1, characterized in that after intramolecular coupling reaction, organic solvent is added for extraction, and after organic phase is dried and removed, column chromatography is used for separation to obtain the target product.
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