CN108017582B - Synthetic method of bromine-containing 1, 3-isoquinolinedione derivative - Google Patents
Synthetic method of bromine-containing 1, 3-isoquinolinedione derivative Download PDFInfo
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Abstract
The invention provides a method for synthesizing a bromine-containing 1, 3-isoquinoline dione derivative, which comprises the steps of initiating an addition reaction in an organic solvent by taking N-alkyl-N-isopropenyl benzamide and carbon tetrabromide as raw materials in a free radical initiator, distilling under reduced pressure after the reaction is completed to remove the solvent, and separating by column chromatography to obtain a target product. The method has the advantages of low price of reagents required by the reaction, small environmental pollution, low production cost, short reaction steps, mild conditions, simple post-treatment, effective reduction of industrial production cost and suitability for industrial production.
Description
Technical Field
The invention relates to a synthesis method of a bromine-containing 1, 3-isoquinoline dione derivative, belonging to the technical field of chemical synthesis.
Background
The 1, 3-isoquinoline diketone compound is widely present in alkaloids, natural products and medicaments, and is an intermediate of common medicines and pesticides; has analgesic and antitumor effects, and can be used as HIV-1 integrase inhibitor. Bromine is introduced into 1, 3-isoquinoline diketone compounds, so that on one hand, the novel physiological activity can be enhanced or provided for the compounds; on the other hand, the method also provides a plurality of possibilities for further modification and transformation of the 1, 3-isoquinolinedione skeleton. The structural formula of the bromine-containing 1, 3-isoquinoline diketone compound is as follows:
wherein R is1Hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro, ester group, cyano or aryl; r2Is a hydrocarbon group or an aromatic group.
Many methods for synthesizing 1, 3-isoquinoline dione derivatives are reported in domestic and foreign literatures, and the following methods are mainly reported: (1) nonmetallic aryl fluoromethylation of activated alkenes. (Wangqing Kong.; Maria Casimiro.;NoeliaFuentes.；Estibaliz Merino and Cristina Nevado.Angew. Chem. Int. Ed2013, 52, 13086-13090) (2) metal-free α -unsaturated imide trifluoromethylation (Lei Li, Min Deng, Sheng-CaiZHEN, Ya-Ping Xiong, Bin Tan and Xin-Yuan Liu.Org.Lett2014, 16, 504-J. Org. Chem.2015, 80, 5730 and 5736) (4) synthesis of perfluoroisoquinoline by cyclization of the olefin under visible light irradiation. (Shi Tang, You-Lin Deng, Jieli, Wen-XinWang, Guo-Liang Ding, Ming-Wei Wang, Zhu-Ping Xiao, Ying-Chun Wang and Rui-Long Sheng).J. Org. Chem.2015, 80, 12599-12605.) (5) free-radical mediated cyclization of perfluoroor cyanated isoquinoline by benzamide. (You-Lin Deng, ShiTang, Guo-Liang Ding, Ming-Wei Wang, Jieli, Zeng-Zeng Li, Li Yuan and Rui-Long Sheng.Org. Biomol. Chem.2016, 14, 9348-9353.) (6) palladium catalyzed free radical cascaded difluoroalkylation/cyclization of ethyl difluorobromoacetate with acrylamide. (Xiao-Feng Xia, Su-Li Zhu, Yuan Li and Haijun Wang.RSC Adv.2016, 6, 51703-51709 (7) preparation of 1, 3-isoquinolinedione derivatives using methacryloylbenzamide and benzyl alcohol and sodium phenylsulfinate. (Qiujie Tang, Ping Xie, Jin Wang, Jianjun Lin, ChunlaiFeng, Charles U.Pittman Jr, Aihua Zhou. tetrahedron 2017,73, 5436-containing 5443) (8) a cascade alkylation reaction of substituted n-alkenylbenzamides. (Ping Qian, Bingnan Du, Wei Jiano, Haibo Mei, Jianlin Han and YIPan.Beilstein J. Org. Chem.2016,12,301-308.) (9) oxidative decarbonylation coupling of aliphatic aldehyde with methacrylamide to prepare the 1, 3-isoquinolinedione derivative. (ChangduoPan, Chaoyue Chen and Jin-Tao Yu. org. Biomol. chem., 2017,15, 1096). In some of the above methods for synthesizing 1, 3-isoquinolinedione derivatives, expensive metal catalysts and photocatalysts are used, which increases the cost and has a great negative effect on the environment. These disadvantages have hindered the application of the above synthetic method to industrial production.
Disclosure of Invention
The invention aims to provide a synthetic method of a bromine-containing 1, 3-isoquinolinedione derivative, which is low in cost, green and environment-friendly, convenient to operate and suitable for industrial production, aiming at the defects of the prior art.
The invention relates to a method for synthesizing a bromine-containing 1, 3-isoquinoline dione derivative, which comprises the steps of taking N-alkyl-N-isopropenyl benzamide and carbon tetrabromide as raw materials in an organic solvent, initiating by a free radical initiator to carry out heating reaction until the reaction completely passes through the series-connected free radical addition cyclization process to obtain a product, carrying out reduced pressure distillation to remove the solvent after the reaction is completely finished, and carrying out column chromatography separation to obtain a target product.
The organic solvent is 1, 4-dioxane, anisole, acetone, tetrahydrofuran or N, N-dimethylformamide.
The molar ratio of the substrate N-alkyl-N-isopropenyl benzamide to the carbon tetrabromide is 1: 1-1: 2.
The free radical initiator is cumene hydroperoxide, di-tert-butyl peroxide, hydrogen peroxide, m-chloroperoxybenzoic acid, peracetic acid, tert-butyl hydroperoxide, benzoyl peroxide, urea peroxide or tert-butyl peroxybenzoate.
The reaction temperature of the addition reaction is 30-70 ℃, and the reaction time is 2-36 hours.
Compared with the prior art, the invention has the following advantages:
1. reagents required by the reaction are low in price, high in safety and small in environmental pollution;
2. the reaction steps are short, the synthesis conditions are mild, the post-treatment is simple, and the production cost is low;
3. the reaction rate is high, the required time is short, the reaction efficiency is high, and the reaction yield is high.
Detailed Description
The synthesis of the bromine-containing 1, 3-isoquinolinedione derivatives of the present invention is further illustrated below with reference to specific examples.
Example 1: synthesis of 4-bromomethyl-2, 4-dimethyl-4H-isoquinoline-1, 3-dione
Adding magnetons into a 25ml reaction tube, and sequentially adding raw material N-methyl-N-isopropenyl benzylAmide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, were stirred at 50 ℃ for 2 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a white powdery pure product, namely 4-bromomethyl-2, 4-dimethyl-4H-isoquinoline-1, 3-diketone with the yield of 86%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.28 (d,J= 8.6 Hz, 1H), 7.69(t,J= 8.2 Hz, 1H), 7.50 (t,J= 7.9 Hz, 1H), 7.39 (d,J= 7.9 Hz, 1H), 4.16(d,J= 9.9 Hz, 1H), 3.67 (d,J= 9.9 Hz, 1H), 3.41 (s, 3H), 1.72 (s, 3H).13CNMR (151 MHz, CDCl3) 174.2, 164.0, 141.1, 134.2, 129.0, 128.1, 125.3,124.6, 49.1, 40.2, 28.3, 27.3。
example 2: synthesis of 4-bromomethyl-2, 4, 6-trimethyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding raw materials of N-methyl-N-isopropenyl-6-methylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 2 hours; and (2) carrying out column chromatography separation after removing the solvent by reduced pressure distillation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) to obtain a white powdery pure product, namely 4-bromomethyl-2, 4,6 trimethyl-4H-isoquinoline-1, 3-diketone, wherein the yield is 86%, and the synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.16 (d,J= 8.0 Hz, 1H), 7.30(d, 1H), 7.16 (s, 1H), 4.15 (d,J= 9.8 Hz, 1H), 3.66 (d,J= 9.8 Hz, 1H),3.40 (s, 3H), 2.47 (s, 3H), 1.70 (s, 3H).13C NMR (151 MHz, CDCl3) 174.4,164.0, 145.1, 141.1, 129.18, 129.0, 125.0, 122.9, 49.1, 40.3, 28.3, 27.2,22.0.
example 3: synthesis of 4-bromomethyl-2, 4, 7-trimethyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding raw materials of N-methyl-N-isopropenyl-7-methylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 11 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a white solid product, namely 4-bromomethyl-2, 4,7 trimethyl-4H-isoquinoline-1, 3-diketone, wherein the yield is 94%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (400 MHz, CDCl3) 8.08 (s, 1H), 7.49 (d,J= 8.0,0.5 Hz, 1H), 7.28 (d,J= 8.1 Hz, 1H), 4.14 (d,J= 9.8 Hz, 1H), 3.65 (d,J=9.8 Hz, 1H), 3.40 (s, 3H), 2.44 (s, 3H), 1.69 (s, 3H).13C NMR (151 MHz, CDCl3)174.4, 164.1, 138.2, 138.1, 135.2, 129.1, 125.1, 124.5, 48.9, 40.4, 28.2,27.3, 21.0。
example 4: synthesis of 4-bromomethyl-2, 4, 8-trimethyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding raw materials of N-methyl-N-isopropenyl-8-methylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 12 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a white solid product, namely 4-bromomethyl-2, 4,8 trimethyl-4H-isoquinoline-1, 3-diketone, wherein the yield is 85%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 7.52 (t,J= 7.7 Hz, 1H), 7.29(d,J= 7.4 Hz, 1H), 7.27 (d,J= 7.9 Hz, 1H), 4.17 (d,J= 9.9 Hz, 1H), 3.66(d,J= 9.9 Hz, 1H), 3.38 (s, 3H), 2.80 (s, 3H), 1.71 (s, 3H).13C NMR (151MHz, CDCl3) 173.9, 164.4, 142.7, 142.3, 133.0, 132.1, 123.7, 122.9, 49.1,40.6, 28.7, 27.3, 24.0。
example 5: synthesis of 6-bromo-4-bromomethyl-2, 4 dimethyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by the sequential addition of the starting materials N-methyl-N-isopropenyl-6-bromobenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of solvent (1, 4-dioxane), 15% mol cumene hydroperoxide, and stirring at 50 ℃ for 11 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a white solid product, namely 6-bromo-4-bromomethyl-2, 4 dimethyl-4H-isoquinoline-1, 3-dione, wherein the yield is 74%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.12 (d,J= 8.4 Hz, 1H), 7.62(dd,J= 8.4, 1.8 Hz, 1H), 7.53 (d,J= 1.8 Hz, 1H), 4.12 (d,J= 10.0 Hz,1H), 3.60 (d,J= 10.0 Hz, 1H), 3.38 (s, 3H), 1.70 (s, 3H).13C NMR (151 MHz,CDCl3) 173.5, 163.2, 142.8, 131.7, 130.6, 129.4, 128.0, 124.3, 49.1, 39.9,28.1, 27.4。
example 6: synthesis of 6-methoxy-4-bromomethyl-2, 4 dimethyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding raw materials of N-methyl-N-isopropenyl-6-methoxybenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 4 hours; reducingAnd (3) removing the solvent by pressure distillation, and then performing column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) to obtain a white solid product, namely 6-methoxy-4-bromomethyl-2, 4-dimethyl-4H-isoquinoline-1, 3-dione, wherein the yield is 92%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.22 (d,J= 8.8 Hz, 1H), 7.00(d,J= 11.2 Hz, 1H), 6.82 (d,J= 2.4 Hz, 1H), 4.14 (d,J= 9.9 Hz, 1H),3.90 (s, 3H), 3.62 (d,J= 9.8 Hz, 1H), 3.38 (s, 3H), 1.70 (s, 3H).13C NMR(151 MHz, CDCl3) 174.3, 164.3, 163.6, 143.3, 131.4, 118.3, 113.5, 110.2,55.6, 49.3, 40.2, 28.4, 27.1。
example 7: synthesis of 4-bromomethyl-2-ethyl-4-methyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding raw materials of N-ethyl-N-isopropenylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 3 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a colorless oily liquid product, namely 4-bromomethyl-2-ethyl-4-methyl-4H-isoquinoline-1, 3-diketone with the yield of 88%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.27 (d,J= 7.9, 1.0 Hz, 1H),7.68 (t, 1H), 7.49 (t, 1H), 7.38 (d,J= 7.9 Hz, 1H), 4.15 (d,J= 9.9 Hz,1H), 4.09 (dd,J= 7.1, 2.8 Hz, 1H), 4.06 (q,J= 7.1, 1H), 3.65 (d,J= 9.8Hz, 1H), 1.70 (s, 3H), 1.23 (t,J= 7.1 Hz, 3H).13C NMR (151 MHz, CDCl3)173.7, 163.4, 141.1, 134.1, 129.0, 128.0, 125.5, 124.6, 48.8, 40.5, 35.9,28.1, 13.0。
example 8: synthesis of 4-bromomethyl-2-n-butyl-4-methyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding the starting materials N-N-butyl-N-isopropenylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 3 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a colorless oily liquid product, namely 4-bromomethyl-2-n-butyl-4-methyl-4H-isoquinoline-1, 3-diketone, with the yield of 85%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.27 (d,J= 9.0 Hz, 1H), 7.67(t,J= 8.3 Hz, 1H), 7.49 (t,J= 8.0 Hz, 1H), 7.38 (d,J= 7.9 Hz, 1H), 4.16(d,J= 9.9 Hz, 1H), 4.07-3.98 (m, 2H), 3.66 (d,J= 9.9 Hz, 1H), 1.70 (s,3H), 1.66-1.58 (m, 2H), 1.42-1.34 (m, 2H), 0.94 (t,J= 7.4 Hz, 3H).13C NMR(151 MHz, CDCl3) 173.9, 163.6, 141.2, 134.1, 129.0, 128.0, 125.5, 124.6,48.9, 40.6, 40.34, 29.9, 28.3, 20.3, 13.8。
example 9: synthesis of 4-bromomethyl-2-phenyl-4-methyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by sequentially adding raw materials of N-phenyl-N-isopropenylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of a solvent (1, 4-dioxane), 15% mol of cumene hydroperoxide, and stirring at 50 ℃ for 3 hours; and (3) carrying out column chromatography separation after removing the solvent by reduced pressure distillation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) to obtain a white powdery solid product, namely 4-bromomethyl-2-phenyl-4-methyl-4H-isoquinoline-1, 3-diketone, wherein the yield is 76%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, cdcl3) 8.31 (d,J= 8.8 Hz, 1H), 7.75(t,J= 8.3 Hz, 1H), 7.57-7.42 (m, 6H), 7.24 (d,J= 7.5 Hz, 1H), 4.19 (d,J= 9.8 Hz, 1H), 3.72 (d,J= 9.8 Hz, 1H), 1.84 (s, 3H).13C NMR (151 MHz, CDCl3)174.2, 163.9, 141.2, 135.3, 134.6, 129.3, 129.3, 128.7, 128.3, 128.25,125.6, 124.8, 49.4, 41.2, 27.8。
example 10：Synthesis of 4-bromomethyl-2-benzyl-4-methyl-4H-isoquinoline-1, 3-dione
A25 ml reaction tube was charged with magnetons, followed by the sequential addition of the starting materials N-benzyl-N-isopropenylbenzamide (0.5 mmol) and carbon tetrabromide (0.75 mmol), 5ml of solvent (1, 4-dioxane), 15% mol cumene hydroperoxide. Stirring at 50 ℃ for 3 hours; and (3) carrying out column chromatography separation (silica gel: 200-300 meshes, and the volume ratio of an eluent is petroleum ether: ethyl acetate =15: 1) after removing the solvent by reduced pressure distillation to obtain a white solid product, namely 4-bromomethyl-2-benzyl-4-methyl-4H-isoquinoline-1, 3-diketone, wherein the yield is 83%. The synthetic formula is as follows:
the nuclear magnetic data are as follows:1H NMR (600 MHz, CDCl3) 8.28 (d,J= 7.9, 1.0 Hz, 1H),7.69(t, 1H), 7.50 (t, 1H), 7.43 (d,J= 7.2 Hz, 2H), 7.39 (d,J= 7.9 Hz,1H), 7.29 (t,J= 7.5 Hz, 2H), 7.23 (t,J= 7.3 Hz, 1H), 5.26 (d,J= 14.0Hz, 1H), 5.19 (d,J= 14.0 Hz, 1H), 4.19 (d,J= 9.9 Hz, 1H), 3.68 (d,J=9.9 Hz, 1H), 1.70 (s, 3H).13C NMR (151 MHz, CDCl3) 174.1, 163.6, 141.2,136.8, 134.3, 129.2, 128.5, 128.4, 128.1, 127.4, 125.3, 124.6, 49.3, 43.9,40.0, 28.5。
Claims (3)
1. a synthetic method of bromine-containing 1, 3-isoquinoline dione derivatives is characterized in that N-alkyl-N-isopropenyl benzamide and carbon tetrabromide are used as raw materials in an organic solvent, an addition reaction is initiated by a free radical initiator, after the reaction is completed, the solvent is removed by reduced pressure distillation, and column chromatography separation is carried out to obtain a target product;
the organic solvent is 1, 4-dioxane, anisole, acetone, tetrahydrofuran or N, N-dimethylformamide;
the free radical initiator is cumene hydroperoxide, di-tert-butyl peroxide, hydrogen peroxide, m-chloroperoxybenzoic acid, peracetic acid, tert-butyl hydroperoxide, benzoyl peroxide, urea peroxide or tert-butyl peroxybenzoate;
the structural formula of the raw material N-alkyl-N-isopropenyl benzamide is as follows:
the structural formula of the bromine-containing 1, 3-isoquinoline diketone compound is as follows:
in the formula, R1Is hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro, ester group, cyano or aryl, R2Is a hydrocarbyl group.
2. The method for synthesizing a bromine-containing 1, 3-isoquinolinedione derivative as claimed in claim 1, characterized in that: the molar ratio of the substrate N-alkyl-N-isopropenyl benzamide to the carbon tetrabromide is 1: 1-1: 2.
3. The method for synthesizing a bromine-containing 1, 3-isoquinolinedione derivative as claimed in claim 1, characterized in that: the reaction temperature of the addition reaction is 30-70 ℃, and the reaction time is 2-36 hours.
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