Method for synthesizing quinazolinone and derivatives thereof through photocatalytic three-component cascade reaction
By photocatalyzing a three-component tandem reaction, quinazolinone is synthesized by using aldehyde, isatin anhydride, ammonium formate or amine and 4CzIPN under mild conditions, solving the problems of harsh reaction conditions and metal residues in traditional synthesis methods, achieving high efficiency , the synthesis of quinazolinone without residues has important research and industrial application value.
Patent Information
- Application Number
- CN202411533494.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-10-31
- Publication Date
- 2025-01-03
AI Technical Summary
The reaction conditions of traditional quinazolinone compounds are harsh, and metal residues may exist in the product, which affects its application in the field of active raw materials, and there is a lack of efficient synthesis methods under mild conditions.
Using photocatalytic three-component tandem reaction, using cheap and easy-to-get aldehyde, isatin anhydride, ammonium formate or amine as raw materials, 4CzIPN as photocatalyst, DMSO as solvent, and reacting at 60-100°C by blue light irradiation to achieve quinazole High-efficiency synthesis of linone and its derivatives.
The efficient synthesis of quinazolinone and its derivatives under mild conditions is achieved, with high yields and no metal residues, providing a novel synthesis strategy with extensive research and industrial application prospects.
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Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of pharmaceutical chemical intermediate synthesis, relates to the synthesis of quinazolinone and its derivatives, and particularly relates to a method for synthesizing quinazolinone and its derivatives through a photocatalytic three-component tandem reaction. Background Art
[0002] Nitrogen-containing heterocyclic compounds are widely present in medicines, pesticides, natural products and various functional materials. They play an important role in natural products and synthetic drugs and have always been a hot topic for organic synthetic chemists. Quinazolinone compounds, as a very classic drug molecular skeleton, are an important component of nitrogen-containing heterocyclic compounds. Their derivatives show good biological and pharmacological activities in medicine, such as antiviral, anticancer, hypoglycemic, hypotensive, diuretic, antihypertensive and insecticidal sterilization. The following are active pharmaceutical ingredients containing quinazolinone compound structural units.
[0003]
[0004] In recent years, there have been many reports on the synthesis of quinazolinone compounds. Traditional synthesis methods mostly use o-aminobenzamide, aldehydes, alcohols, styrenes and other compounds as raw materials, and need to be carried out under the catalysis of transition metals such as iridium, ruthenium, palladium, nickel, iron, copper, etc. (J.Org.Chem.2017,82,7165-7175; J.Org.Chem.2011,76,7730-7736; RSCAdv.,2016,6,65196; Adv.Synth.Catal.,2015,13,2862-2868; Org.Biomol.Chem.,2020,18,5435-5441; J.Org.Chem.,1984,49,788-793; 3,1096-1099; Organic Letters 2020, 22, 8382-8386), and the reaction conditions are harsh, resulting in a low product yield. More importantly, the use of metal catalysts may result in metal residues in the product, which greatly affects its application in the field of living raw materials.
[0005] In recent years, photocatalytic reactions have become a research hotspot in the field of synthetic chemistry due to their mild reaction conditions and good functional group compatibility. They have shown excellent application potential and are an important alternative strategy to traditional transition metal catalytic reactions. Therefore, it is of great significance to develop a new method for the simple and efficient photocatalytic synthesis of quinazolinone derivatives under mild conditions. Summary of the invention
[0006] In view of the shortcomings of the prior art, the purpose of the present invention is to provide a method for preparing quinazolinone and its derivatives by a simple and efficient photocatalytic three-component tandem reaction. The method uses cheap and readily available aldehydes, isatoic anhydride, ammonium formate or amine as initial raw materials, 4CzIPN as a photocatalyst, DMSO as a solvent, mild reaction conditions, simple post-treatment, and a high yield "one-pot method" to achieve the synthesis of quinazolinone and its derivatives, providing a new strategy for the synthesis of such compounds.
[0007] The present invention is achieved through the following technical solutions:
[0008] A method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction comprises the following steps:
[0009] The isatoic anhydride of formula I, the aldehyde compound of formula II, and the ammonium formate or primary amine of formula III are dissolved in an organic solvent, and react under the combined action of a photocatalyst, light, a solvent, and an additive at a certain temperature to generate a series of quinazolinones and derivatives thereof of formula IV, and after the reaction is completed, a crude product is separated and purified to obtain a quinazolinone derivative;
[0010]
[0011] Wherein, R1 is selected from methyl, methoxy, fluorine, bromine, and chlorine;
[0012] R2 is selected from the group consisting of n-propyl, isopropyl, n-butyl, n-octyl, cyclohexyl, phenyl, 4-methylphenyl, 3-methylphenyl, 4-methoxyphenyl, 4-tert-butylphenyl, 4-isopropylphenyl, 3,4-dimethylphenyl, 4-nitrophenyl, 4-halogen (F, Cl, Br) phenyl, 4-trifluoromethylphenyl, 4-cyanophenyl, 2-propenyloxyphenyl, 2-ethoxyphenyl, 4-hydroxyphenyl, 4-phenoxyphenyl, , styryl, 2-thienyl-, 2-pyridyl, 2-furyl, 3-indolyl, 2-quinolyl;
[0013] R3 is selected from isopropyl, cyclohexyl, benzyl, phenyl, 4-methoxyphenyl, 4-methylphenyl.
[0014] A further improvement of the present invention is:
[0015] The photocatalyst is terpyridyl ruthenium chloride (Ru(bpy)3Cl2), 9-mesityl-10-methylacridine perchlorate (Acr-Mes-Me + ClO4 -), 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile (4CzIPN), 2,4,5,6-tetrakis(diphenylamino)-isophthalonitrile (4DPAIPN), 2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile (3DPAFIPN), 2,4,5,7-tetrabromofluorescein (EosinY), rhodamine B (Rhodamine B), 2,4,6-triphenylpyran tetrafluoroborate (TPPT) or 9-fluorenone, or a mixture of two or more thereof.
[0016] Furthermore, the organic solvent is one or a mixture of two or more of acetonitrile, ethanol, 1,4-dioxane, chlorobenzene, dimethyl sulfoxide, DMF, tert-butyl alcohol, tert-amyl alcohol, 1,2-dichloroethane, water and toluene.
[0017] Furthermore, the additive is one or a mixture of two or more of acetic acid, hydrochloric acid, p-toluenesulfonic acid, ethylenediaminediacetic acid, Cu(OTf)3, and Ga(OTf)3.
[0018] Furthermore, the light is one of sunlight, red light, blue light, yellow light, green light, purple light, infrared light or ultraviolet light, or a mixture of two or more thereof.
[0019] Furthermore, the molar ratio of the isatoic anhydride to the aldehyde compound, ammonium formate or amine compound, photocatalyst and additive is 1:1.5-2.0:2.0-3.0:0.01-0.03:0.05-0.1.
[0020] Preferably, the photocatalyst is 4CzIPN.
[0021] The illumination condition is blue light with a wavelength of 465 nm.
[0022] The solvent is dimethyl sulfoxide.
[0023] The additive is acetic acid.
[0024] Furthermore, the reaction temperature is 60-100° C., and the reaction time is 10-18 hours; the separation process includes washing, extraction, separation, drying, and then removing the organic phase to obtain a crude product; the purification method is column chromatography or recrystallization, the column chromatography eluent is dichloromethane and ethyl acetate, and the mixing ratio is dichloromethane:ethyl acetate=10:1~1:1; the recrystallization solvent is methanol or ethanol.
[0025] Compared with the prior art, the present invention has the following beneficial effects:
[0026] The method uses cheap and readily available aldehydes, isatoic anhydride, ammonium formate or amine as starting materials, 4CzIPN as a photocatalyst, DMSO as a solvent, mild reaction conditions, simple post-treatment, and a high-yield "one-pot" method to achieve the synthesis of quinazolinone and its derivatives, providing a new strategy for the synthesis of this class of compounds.
[0027] The invention uses cheap and readily available aldehydes, isatoic anhydride, ammonium formate or amine as initial raw materials, realizes efficient synthesis of quinazolinone and its derivatives under mild photocatalytic conditions, and has high research value and broad industrial application prospects. DETAILED DESCRIPTION
[0028] The present invention is described in detail below in conjunction with specific embodiments.
[0029] Example 1: Synthesis of 2-phenylquinazoline-4(3H)-one
[0030]
[0031] Isatoic anhydride (0.5mmol), benzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by reduced pressure rotary evaporation to obtain a crude product; the crude product was purified by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a white solid pure product with a yield of 84%.
[0032] Example 2: Synthesis of 2-(4-methoxyphenyl)quinazolin-4(3H)-one
[0033]
[0034] Isatoic anhydride (0.5mmol), 4-methoxybenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a pure white solid product with a yield of 89%.
[0035] Example 3: Synthesis of 2-(4-methylphenyl)quinazolin-4(3H)-one
[0036]
[0037] Isatoic anhydride (0.5mmol), 4-methylbenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a white solid pure product with a yield of 86%.
[0038] Example 4: Synthesis of 2-(2-ethoxyphenyl)quinazolin-4(3H)-one
[0039]
[0040] Isatoic anhydride (0.5mmol), 2-ethoxybenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a white solid pure product with a yield of 82%.
[0041] Example 5: Synthesis of 2-(2-propenyloxyphenyl)quinazolin-4(3H)-one
[0042]
[0043] Isatoic anhydride (0.5mmol), 2-propyleneoxybenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum rotary evaporation to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a white solid pure product with a yield of 80%.
[0044] Example 6: Synthesis of 2-(4-phenoxyphenyl)quinazolin-4(3H)-one
[0045]
[0046] Isatoic anhydride (0.5mmol), 4-phenoxybenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a pure white solid product with a yield of 83%.
[0047] Example 7: Synthesis of 2-(3,4-dimethoxyphenyl)quinazolin-4(3H)-one
[0048]
[0049] Isatoic anhydride (0.5mmol), 3,4-dimethoxybenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a white solid pure product with a yield of 88%.
[0050] Example 8: Synthesis of 2-(4-hydroxyphenyl)quinazolin-4(3H)-one
[0051]
[0052] Isatoic anhydride (0.5mmol), 4-hydroxybenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a white solid pure product with a yield of 80%.
[0053] Example 9: Synthesis of 2-(4-fluorophenyl)quinazolin-4(3H)-one
[0054]
[0055] Isatoic anhydride (0.5mmol), 4-fluorobenzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a pure white solid product with a yield of 76%.
[0056] Example 10: Synthesis of 2-(2-thienyl)quinazolin-4(3H)-one
[0057]
[0058] Isatoic anhydride (0.5mmol), 2-thiophenecarboxaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a pure white solid product with a yield of 78%.
[0059] Example 11: Synthesis of 2-cyclohexylquinazoline-4(3H)-one
[0060]
[0061] Isatoic anhydride (0.5mmol), cyclohexylcarboxaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a pure white solid product with a yield of 70%.
[0062] Example 12: Synthesis of 2,3-diphenylquinazoline-4(3H)-one
[0063]
[0064] Isatoic anhydride (0.5mmol), cyclohexylcarboxaldehyde (0.6mmol, 1.2eq.), aniline (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a pure white solid product with a yield of 75%.
[0065] Example 13: Synthesis of 3-isopropyl-2-phenylquinazoline-4(3H)-one
[0066]
[0067] Isatoic anhydride (0.5mmol), benzaldehyde (0.6mmol, 1.2eq.), isopropylamine (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a white solid pure product with a yield of 72%.
[0068] Example 14: Synthesis of 3-benzyl-2-phenylquinazoline-4(3H)-one
[0069]
[0070] Isatoic anhydride (0.5mmol), benzaldehyde (0.6mmol, 1.2eq.), benzylamine (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of dimethyl sulfoxide were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a pure white solid product with a yield of 68%.
[0071] Comparative Example 1
[0072] The photocatalyst in this comparative example is Acr-Mes-Me + ClO4 - , other operations are the same as in Example 1.
[0073] Isatoic anhydride (0.5 mmol), benzaldehyde (0.6 mmol, 1.2 eq.), ammonium formate (1 mol, 2 eq.), acetic acid (5 mol%), photocatalyst Acr-Mes-Me + ClO4 - (3 mol%) and 2 mL of dimethyl sulfoxide were added sequentially into a 25 mL reaction tube, and the mixture was reacted at 60°C under blue LED (465 nm) irradiation for 10 h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a white solid pure product with a yield of 26%.
[0074] Comparative Example 2
[0075] The solvent in this comparative example is toluene, and other operations are the same as those in Example 1.
[0076] Isatoic anhydride (0.5mmol), benzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of toluene were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (465nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain a pure white solid product with a yield of 65%.
[0077] Comparative Example 3
[0078] In this comparative example, the wavelength range of the blue LED is 440 nm, and other operations are the same as those in Example 1.
[0079] Isatoic anhydride (0.5mmol), benzaldehyde (0.6mmol, 1.2eq.), ammonium formate (1mol, 2eq.), acetic acid (5mol%), photocatalyst 4CzIPN (3mol%) and 2mL of toluene were added to a 25mL reaction tube in sequence, and the mixture was reacted at 60°C under blue LED (445nm) irradiation for 10h; then extracted with ethyl acetate, washed with water three times, and then the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was separated by column chromatography (ethyl acetate: petroleum ether = 2:1) to obtain a pure white solid product with a yield of 54%.
[0080] The above embodiments are only for illustrating the technical concept and features of the present invention, and their purpose is to enable people familiar with the technology to understand the content of the present invention and implement it accordingly, and they cannot be used to limit the protection scope of the present invention. Any equivalent transformation or modification made according to the spirit of the present invention should be included in the protection scope of the present invention.
Claims
1. A method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction, characterized in that: The following steps are involved: The isatoic anhydride of formula I, the aldehyde compound of formula II, and the ammonium formate or primary amine of formula III are dissolved in an organic solvent, and react under the combined action of a photocatalyst, light, a solvent, and an additive at a certain temperature to generate a series of quinazolinones and derivatives thereof of formula IV, and after the reaction is completed, a crude product is separated and purified to obtain a quinazolinone derivative; Wherein, R1 is selected from methyl, methoxy, fluorine, bromine, and chlorine; R2 is selected from the group consisting of n-propyl, isopropyl, n-butyl, n-octyl, cyclohexyl, phenyl, 4-methylphenyl, 3-methylphenyl, 4-methoxyphenyl, 4-tert-butylphenyl, 4-isopropylphenyl, 3,4-dimethylphenyl, 4-nitrophenyl, 4-halogen (F, Cl, Br) phenyl, 4-trifluoromethylphenyl, 4-cyanophenyl, 2-propenyloxyphenyl, 2-ethoxyphenyl, 4-hydroxyphenyl, 4-phenoxyphenyl, , styryl, 2-thienyl-, 2-pyridyl, 2-furyl, 3-indolyl, 2-quinolyl; R3 is selected from isopropyl, cyclohexyl, benzyl, phenyl, 4-methoxyphenyl, 4-methylphenyl.
2. The method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction according to claim 1, characterized in that: The photocatalyst is one or a mixture of two or more of terpyridyl ruthenium chloride, 9-mesityl-10-methylacridine perchlorate, 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile, 2,4,5,6-tetrakis(diphenylamino)-isophthalonitrile, 2,4,6-tris(diphenylamino)-5-fluoroisophthalonitrile, 2,4,5,7-tetrabromofluorescein, rhodamine B, 2,4,6-triphenylpyran tetrafluoroborate or 9-fluorenone.
3. The method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction according to claim 1, characterized in that: The organic solvent is one or a mixture of two or more of acetonitrile, ethanol, 1,4-dioxane, chlorobenzene, dimethyl sulfoxide, DMF, tert-butyl alcohol, tert-amyl alcohol, 1,2-dichloroethane, water and toluene.
4. The method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction according to claim 1, characterized in that: The additive is one of acetic acid, hydrochloric acid, p-toluenesulfonic acid, ethylenediaminediacetic acid, Cu(OTf)3, and Ga(OTf)3, or a mixture of two or more thereof.
5. The method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction according to claim 1, characterized in that: The light is one of sunlight, red light, blue light, yellow light, green light, purple light, infrared light or ultraviolet light, or a mixture of two or more thereof.
6. The method for synthesizing quinazolinone and its derivatives by photocatalytic three-component tandem reaction according to claim 1, characterized in that: The molar ratio of the isatoic anhydride to the aldehyde compound, the ammonium formate or amine compound, the photocatalyst and the additive is 1:1.5-2.0:2.0-3.0:0.01-0.03:0.05-0.
1.
7. The method for synthesizing quinazolinone derivatives by photocatalytic three-component tandem reaction according to claim 5, characterized in that: The illumination condition is blue light with a wavelength of 465 nm.
8. The method for synthesizing quinazolinone derivatives by photocatalytic three-component tandem reaction according to claim 3, characterized in that: The solvent is dimethyl sulfoxide.
9. The method for synthesizing quinazolinone derivatives by photocatalytic three-component tandem reaction according to claim 4, characterized in that: The additive is acetic acid.
10. The method for synthesizing quinazolinone derivatives by photocatalytic three-component tandem reaction according to claim 1, characterized in that: The reaction temperature is 60-100° C., and the reaction time is 10-18 hours. The separation process includes washing with water, extracting, separating liquids, and removing the organic phase after drying to obtain a crude product. The purification method is column chromatography or recrystallization, and the column chromatography eluent is dichloromethane and ethyl acetate, and the mixing ratio is dichloromethane:ethyl acetate=10:1-1:1; the recrystallization solvent is methanol or ethanol.