CN114773354A - Simple synthesis method of Trisphaeridine - Google Patents
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Abstract
The invention relates to a simple synthesis method of Trisphaeridine, which comprises the following specific steps: s1, dissolving 6-bromo-3, 4-methylenedioxybenzaldehyde and phenylboronic acid in a solvent, and adding K2CO3In N, at2Addition of Pd (OAC) under atmospheric pressure2Performing Suzuki coupling reaction, purifying to obtain 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde; s2, reacting 6-phenylbenzo [ d ]][1,3]Adding dioxolane-5-formaldehyde and ammonium formate into a photoreaction bottle, then adding 1,1,1,3,3, 3-hexafluoro-2-propanol, stirring for dissolving, then carrying out 6 pi electrical cyclization reaction under visible light irradiation, and purifying after the reaction is finished to obtain the Trisphaeridine. The synthesis method disclosed by the invention is mild in reaction conditions, short in synthesis route, low in cost of required raw materials, free of toxic waste and high in overall yield.
Description
Technical Field
The invention belongs to the technical field of heterocyclic compounds, and particularly relates to a simple synthesis method of Trisphaeridine.
Background
Cancer is one of the major diseases threatening human health at present, and it is counted that cancer is the second cause of death among residents of various countries worldwide, and thus, the development of a drug for treating cancer is urgent.
The benzophenanthridine natural alkaloid has wide application rangeDue to the fact that the special plane structure of the general physiological activity can act on topoisomerase, the activity of benzophenanthridine natural alkaloids in the aspect of tumor resistance is greatly concerned, and researches show that the benzophenanthridine natural alkaloids have wide anti-tumor activity and strong activity. Wherein Trisphaeridine is a relatively representative benzophenanthridine natural alkaloid, and can be separated from Amaryllidaceae plant Narcissus astragalis (Narcissus astrriensis). Researchers find that the alkaloid has good inhibitory activity on human lung cancer cells A-549, human liver cancer cells hepg and human colon cancer cells ht-29 in the research process of the anti-tumor activity of the alkaloid, and the IC50 of the alkaloid on the three tumor cells is more than 40 mu mol.L-1Indicating that Trisphaeridine has potential application in the treatment of the three types of cancers.
Therefore, many scientific researchers carry out synthesis research on Trisphaeridine so as to develop a simple, convenient, green and efficient synthesis route. At present, the synthetic methods of the alkaloid are many, but most of the methods need complicated steps, and the post-treatment is complex and is not environment-friendly. The method can synthesize the alkaloid through two simple reaction steps, has cheap and easily obtained raw materials, simple and convenient post-treatment, environmental protection, higher yield and lower comprehensive cost.
Disclosure of Invention
The invention aims to solve the technical problem of providing a simple synthesis method of Trisphaeridine aiming at the defects in the prior art, and the method has the advantages of greenness, high efficiency and simplicity.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
the simple synthesis method of Trisphaeridine is provided, and comprises the following specific steps:
s1, dissolving 6-bromo-3, 4-methylenedioxybenzaldehyde (compound 1) and phenylboronic acid (compound 2) in a solvent, and adding K2CO3(for activating boric acid or boric acid ester to perform metal transfer reaction), stirring uniformly, and introducing N2In N, at2Addition of Pd (OAC) under atmospheric pressure2Carrying out Suzuki coupling reaction, and reactingWashing the reaction solution with water, extracting with ethyl acetate, collecting organic phase, drying, concentrating, and purifying by column chromatography to obtain 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3);
s2, adding the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde (compound 3) obtained in the step S1 and ammonium formate into a photoreaction bottle, then adding 1,1,1,3,3, 3-hexafluoro-2-propanol (HFIP, solvent), stirring and dissolving, then carrying out 6 pi electrocyclic reaction under visible light irradiation, concentrating the reaction solution after the reaction is finished, and purifying by column chromatography to obtain Trisphaeridine.
The synthetic route is as follows:
according to the scheme, the molar ratio of the 6-bromo-3, 4-methylenedioxybenzaldehyde described in S1 to phenylboronic acid is 1: 0.9 to 1.4.
According to the scheme, the solvent in S1 is a mixed solution of N, N-Dimethylformamide (DMF) and water, and the volume ratio of the N, N-dimethylformamide to the water is 2-3: 1, the concentration of the 6-bromo-3, 4-methylenedioxybenzaldehyde in the solvent is 0.2-0.5 mol/L.
According to the scheme, K is obtained in S12CO3The mol ratio of the compound to 6-bromo-3, 4-methylenedioxybenzaldehyde is 1: 0.9 to 1.4.
According to the scheme, the Suzuki coupling reaction conditions of S1 are as follows: reacting for 3-5 hours at 20-30 ℃.
The above scheme is adopted, and the Pd (OAC) described in S12The molar ratio of the formaldehyde to 6-bromo-3, 4-methylenedioxybenzaldehyde is 0.01-0.06: 1.
according to the scheme, the molar ratio of the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde to ammonium formate in S2 is 1: 6 to 11.
According to the scheme, the concentration of the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde in the 1,1,1,3,3, 3-hexafluoro-2-propanol S2 is 0.05-0.3 mol/L.
According to the scheme, the visible light source of the S2 is a purple LED lamp, the power is 3-20W, and the wavelength is 400-420 nm.
According to the scheme, the 6 pi electrocyclization reaction condition of S2 is as follows: reacting for 10-12 hours at 20-35 ℃.
The invention has the beneficial effects that: the synthesis method disclosed by the invention is mild in reaction conditions, short in synthesis route, low in cost of required raw materials, free of toxic wastes and high in overall yield (the total yield is 27.3-46%).
Drawings
FIG. 1 is a NMR chart of Trisphaeridine prepared in example 1 of the present invention;
FIG. 2 is a Trisphaeridine NMR spectrum prepared in example 1.
Detailed Description
In order to make the technical solutions of the present invention better understood, the present invention is further described in detail below with reference to the accompanying drawings.
Example 1
A simple synthesis method of Trisphaeridine (reaction scale is milligram level) comprises the following specific steps:
1) preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (458.0mg, 2.0mmol) and phenylboronic acid (244.0mg, 2.0mmol) were weighed into a 20mL three-necked reaction flask, and 6mL of DMF/H was added2O mixture (volume ratio DMF: H)2O2: 1), adding clean magneton, stirring to dissolve, and weighing K2CO3(276.0mg, 2.0mmol) was added to the reaction mixture, the reaction mixture was stirred at room temperature for 2-5 minutes, and then N was added2Purge for 5 minutes at N2Pd (OAc) under the atmosphere2(22.5mg, 0.1mmol), adding into the reaction solution, sealing, reacting at 25 deg.C for 4 hr, monitoring reaction condition by Thin Layer Chromatography (TLC), adding 48mL water to quench after aldehyde raw material has reacted completely, extracting the mixed solution with ethyl acetate (3 × 20mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and adding anhydrous Na2SO4Drying, filtering, collecting filtrate, evaporating with rotary evaporator to remove solvent to obtain crude product, and separating and purifying by column chromatography to obtain380.5mg of 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 84.1% yield, and an eluent used therein, Petroleum Ether (PE)/Ethyl Acetate (EA), with a polarity of 20:1 to 10: 1;
2) preparing Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde (compound 3) (45.2mg, 0.2mmol) and ammonium formate (126.1mg, 2.0mmol), adding into a dry photoreaction bottle, adding 2mL of HFIP, stirring for dissolving, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for reacting at 25 ℃ for 12 hours, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 23.2mg of yellow solid Trisphaeridine with the yield of 52%, using Petroleum Ether (PE)/Ethyl Acetate (EA) as an eluent and the polarity of 8: 1-4: 1.
Characterization data for Trisphaeridine compounds prepared in this example:
1H NMR(500MHz,CDCl3)δ9.10(s,1H),8.38(dd,J＝8.2,1.5Hz,1H),8.15(dd,J＝8.3,1.5Hz,1H),7.92(s,1H),7.69(ddd,J＝8.3,7.0,1.5Hz,1H),7.63(ddd,J＝8.2,7.0,1.4Hz,1H),7.35(s,1H),6.18(s,2H).
13C NMR(126MHz,CDCl3)δ151.82,151.51,148.23,144.14,130.28,130.07,128.03,126.71,124.30,123.11,122.02,105.53,101.94,99.98.
the nmr hydrogen spectrum and nmr carbon spectrum of Trisphaeridine prepared in this example are shown in fig. 1 and 2.
Example 2
A simple synthesis method of Trisphaeridine (reaction scale is milligram level) comprises the following specific steps:
1) preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (458.0mg, 2.0mmol) and phenylboronic acid (341.4mg, 2.8mmol) were weighed into a 20mL three-necked reaction flask, and 4mL of TMMF/H was added2O mixture (volume ratio DMF: H)2O2: 1), clean magnet is put inStirring to dissolve, and weighing K2CO3(386.4mg, 2.8mmol) was added to the reaction solution, and the reaction solution was stirred at room temperature for 3 minutes, followed by N2Purge for 5 minutes at N2Pd (OAc) under the atmosphere2(27.0mg, 0.12mmol), adding into the reaction solution, sealing, reacting at 25 deg.C for 4 hr, monitoring reaction condition by Thin Layer Chromatography (TLC), adding 48mL water to quench after aldehyde raw material has reacted completely, extracting the mixed solution with ethyl acetate (3 × 20mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and adding anhydrous Na2SO4Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, which is separated and purified by column chromatography to obtain 316.4mg of 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in a yield of 70.1% and an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA) with a polarity of 20:1 to 10: 1;
2) preparing Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (compound 3) (45.2mg, 0.2mmol) and ammonium formate (210.0mg, 1.2mmol) and adding the mixture into a dry photoreaction bottle, adding 4mL of HFIP (high frequency internet protocol) to stir and dissolve, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for reaction at 25 ℃ for 12 hours, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, and separating the crude product by using column chromatography to obtain 17.4mg of yellow solid Trisphaeridine with the yield of 39%, using Petroleum Ether (PE)/Ethyl Acetate (EA) as an eluent and the polarity of 8: 1-4: 1.
Example 3
A simple synthesis method of Trisphaeridine (reaction scale is milligram level) comprises the following specific steps:
1) preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (458.0mg, 2.0mmol) and phenylboronic acid (219.4mg, 1.8mmol) were weighed into a 20mL three-necked reaction flask, and 10mL of TMF/H was added2Mixture of O (volume ratio DMF: H)2O＝2:1), adding clean magnetons, stirring and dissolving, and weighing K2CO3(248.7mg, 1.8mmol) was added to the reaction solution, and the reaction solution was stirred at room temperature for 3 minutes, followed by N2Purge 5 min at N2Pd (OAc) under the atmosphere2(4.5mg, 0.02mmol) in a reaction solution, sealing, reacting at 25 deg.C for 4 hr, monitoring the reaction by Thin Layer Chromatography (TLC), quenching with 48mL of water after the aldehyde raw material has reacted completely, extracting the mixture with ethyl acetate (3X 20mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and adding anhydrous Na2SO4Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, which is separated and purified by column chromatography to obtain 339.4mg of 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 75.1% yield, using an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA) with a polarity of 20:1 to 10: 1;
2) preparation of Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (compound 3) (45.2mg, 0.2mmol) and ammonium formate (138.8mg, 2.2mmol) and adding the mixture into a dry photoreaction bottle, adding 0.7mL of HFIP (high frequency internet protocol) to stir and dissolve the mixture, sealing the mixture, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for reaction at 25 ℃ for 12 hours, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, evaporating the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 19.1mg of yellow solid Trisphaeridine with the yield of 42.9%, using an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA) and the polarity of 8: 1-4: 1.
Example 4
A simple synthesis method of Trisphaeridine (the reaction scale is gram level) comprises the following specific steps:
1) preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (1832.0mg, 8.0mmol) and phenylboronic acid (9760mg, 8.0mmol) were weighed into a 50mL three-necked reaction flask, and 24mL of DMF/H was added2Mixed solution (volume) of OCompared with DMF: h2O2: 1), adding clean magneton, stirring to dissolve, and weighing K2CO3(1104.0mg, 8.0mmol) was added to the reaction mixture, the reaction mixture was stirred at room temperature for 2-5 minutes, and then N was added2Purge for 5 minutes at N2Atmosphere Pd (OAc)2(89.8mg, 0.4mmol), adding into the reaction solution, sealing, reacting at 25 deg.C for 4 hr, monitoring reaction condition by Thin Layer Chromatography (TLC), adding 190mL water to quench after aldehyde raw material is basically reacted completely, extracting the mixed solution with ethyl acetate (3 × 80mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and using anhydrous Na2SO4Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, which is separated and purified by column chromatography to obtain 1517.1mg of 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 83.9% yield, and a Petroleum Ether (PE)/Ethyl Acetate (EA) eluent with a polarity of 20:1 to 10: 1;
2) preparation of Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde (compound 3) (1131.2mg, 5.0mmol) and ammonium formate (3150mg, 50.0mmol) and adding the mixture into a dry photoreaction bottle, adding 50mL of HFIP (high frequency internet protocol) to stir and dissolve, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for reacting at 25 ℃ for 12 hours, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 613.4mg of yellow solid trisporaridine with the yield of 55%, using an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA) and the polarity of 8: 1-4: 1.
From the above examples, it can be seen that the reaction conditions in each step were within the ranges as listed, the reaction yield was higher than that outside the ranges as listed, the yield was not adversely affected in the gram scale reaction, and the improvement was achieved, and it was possible to prepare Trisphaeridine compound on a gram scale in large quantities.
While the foregoing is directed to the preferred embodiment of the present invention, it will be apparent to those skilled in the art that various changes in the solvent used, the catalyst and the reactants used, and the like may be made without departing from the spirit of the invention and such changes are intended to be within the scope of the invention.
Claims (10)
1. A simple synthesis method of Trisphaeridine is characterized by comprising the following specific steps:
s1, dissolving 6-bromo-3, 4-methylenedioxybenzaldehyde and phenylboronic acid in a solvent, and adding K2CO3After stirring evenly, N is introduced2In N, at2Adding Pd (OAC) under atmosphere2Performing Suzuki coupling reaction, washing the reaction solution after the reaction is finished, extracting with ethyl acetate, collecting the organic phase, drying, concentrating, and purifying by column chromatography to obtain 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde;
s2, adding the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde obtained in the step S1 and ammonium formate into a light reaction bottle, then adding 1,1,1,3,3, 3-hexafluoro-2-propanol, stirring and dissolving, then carrying out 6 pi electrical cyclization reaction under visible light irradiation, concentrating the reaction solution after the reaction is finished, and purifying by column chromatography to obtain Trisphaeridine.
2. The simple synthesis method of Trisphaeridine according to claim 1, wherein the molar ratio of 6-bromo-3, 4-methylenedioxybenzaldehyde to phenylboronic acid in S1 is 1: 0.9 to 1.4.
3. The simple synthesis method of Trisphaeridine according to claim 1, wherein the solvent S1 is a mixture of N, N-Dimethylformamide (DMF) and water, and the volume ratio of the DMF to the water is 2-3: 1, the concentration of the 6-bromo-3, 4-methylenedioxybenzaldehyde in the solvent is 0.2-0.5 mol/L.
4. The simplified synthesis method of Trisphaeridine as claimed in claim 1, wherein S1 said K2CO3The mol ratio of the compound to 6-bromo-3, 4-methylenedioxybenzaldehyde is 1: 0.9 to 1.4.
5. The simplified synthesis method of Trisphaeridine according to claim 1, wherein the Suzuki coupling reaction conditions of S1 are as follows: reacting for 3-5 hours at 20-30 ℃.
6. The simple synthesis method of Trisphaeridine as claimed in claim 1, wherein S1 represents Pd (OAC)2The molar ratio of the compound to 6-bromo-3, 4-methylenedioxybenzaldehyde is 0.01-0.06: 1.
7. the simplified method for synthesizing Trisphaeridine as claimed in claim 1, wherein S2 molar ratio of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde to ammonium formate is 1: 6 to 11.
8. The method for synthesizing Trisphaeridine according to claim 1, wherein the concentration of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde in 1,1,1,3,3, 3-hexafluoro-2-propanol is 0.05-0.3 mol/L in S2.
9. The simple synthesis method of Trisphaeridine according to claim 1, wherein the visible light source of S2 is a purple LED lamp, the power is 3-20W, and the wavelength is 400-420 nm.
10. The simple synthesis method of Trisphaeridine according to claim 1, wherein the 6 π electrocyclization reaction conditions of S2 are: reacting for 10-12 hours at 20-35 ℃.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105153172A (en) * | 2015-10-13 | 2015-12-16 | 遵义医学院 | Synthesis method of trisphaeridine |
| CN114232013A (en) * | 2021-11-12 | 2022-03-25 | 华南理工大学 | Method for synthesizing indoloquinoline compound under electrochemical condition |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105153172A (en) * | 2015-10-13 | 2015-12-16 | 遵义医学院 | Synthesis method of trisphaeridine |
| CN114232013A (en) * | 2021-11-12 | 2022-03-25 | 华南理工大学 | Method for synthesizing indoloquinoline compound under electrochemical condition |
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| Title |
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| FERNANDO PORTELA-CUBILLO，等: "Dioxime oxalates; new iminyl radical precursors for syntheses of N-heterocycles", 《TETRAHEDRON》 * |
| FERNANDO PORTELA-CUBILLO，等: "Microwave-Assisted Syntheses of N-Heterocycles Using Alkenone-,Alkynone- and Aryl-carbonyl O-Phenyl Oximes: Formal Synthesis of Neocryptolepine", 《J.ORG.CHEM.》 * |
| JIAN FAN，等: "Expeditious synthesis of phenanthridines through a Pd/MnO2-mediated C-H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids", 《CHEM.COMMUN.》 * |
| RAFAEL ALONSO，等: "Photochemistry of acyloximes: synthesis of heterocycles and natural products", 《TETRAHEDRON》 * |
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