CN113185468A - Method for synthesizing quinazolinone through photocatalysis - Google Patents

Method for synthesizing quinazolinone through photocatalysis Download PDF

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CN113185468A
CN113185468A CN202110477712.2A CN202110477712A CN113185468A CN 113185468 A CN113185468 A CN 113185468A CN 202110477712 A CN202110477712 A CN 202110477712A CN 113185468 A CN113185468 A CN 113185468A
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quinazolinone
anthranilamide
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CN113185468B (en
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王荣周
马松
邢令宝
马德龙
潘琳琳
王才朋
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Shanghai Acorn Chemical Co ltd
Shandong University of Technology
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Shandong University of Technology
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    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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    • C07D239/72—Quinazolines; Hydrogenated quinazolines
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Abstract

The invention discloses a method for synthesizing quinazolinone through photocatalysis, which takes anthranilamide and aldehyde as raw materials, takes fluorescein as a photocatalyst, takes p-toluenesulfonic acid as an auxiliary catalyst, and performs photocatalytic reaction under the irradiation of visible light to obtain quinazolinone. The invention uses the non-metal catalyst, thus reducing the reaction cost; the reaction conditions are mild, and the reaction can be completed at room temperature; simple operation, short reaction time, simple post-treatment, high product yield and more environmental protection. The method not only has higher academic value, but also has certain industrialization prospect.

Description

Method for synthesizing quinazolinone through photocatalysis
Technical Field
The invention relates to a method for synthesizing quinazolinone through photocatalysis, in particular to a method for synthesizing quinazolinone through photocatalysis, which is simple to operate and mild in reaction conditions, and belongs to the technical field of organic synthetic chemistry.
Background
Quinazolinone is an important nitrogen-containing heterocyclic aromatic compound, and has wide biological activity and pharmacological activity, including antibacterial, antiviral, anti-inflammatory, anticonvulsant and anticancer properties. In recent decades, various methods for synthesizing quinazolinones have been developed, but most classical methods still generate quinazolinones by oxidation of an intermediate formed by condensation of anthranilamide and an aldehyde. However, these methods of synthesizing quinazolinones require the use of excess amounts of hazardous oxidizing agents (KMnO)4CuCl, DDQ and MnO2Etc.) or under the combined action of a transition metal catalyst and an oxidant to synthesize the quinazolinone. Longer reaction times and higher reaction temperatures are often required in these synthesis processes. (a) I.Khan, A.Ibrar, N.Abbas and A.Saeed, Eur.J.Med.chem.76 (2014) 193-K244 (b) P.P.Kung, Casper, D.M.K.L.Cook, L.Wilson-Lingard, L.M.Risen, T.A.Vickers, R.Ranken, L.B.Blyn, R.Wyatt, P.D.Cook, D.Ecker, J.Med.Chem.42 (1999) 4705-K4713, (c) N.J.Liverton, D.J.Armstrong, D.A.Claremmon, D.C.Remy, J.Baldwin, R.J.Lynch, G.Zhang, R.Abrus, N.Abrus and J.Cheng.J.Cheng.Y. J.J.Cheng, Q.J.J.Cheng. Cheng.J.J.J.Cheng, Q.J.Cheng.J.J.J.Cheng, Q.J.J.E.J.E.W. Cheng. K. K, C.S. Quaglitato, W.J. Greenlee, A.A. Patchett, R.S.L. Chang, V.J. Lotti, T.B. Chen, S.A. Scheck, K.A. Faust, S.S. Kivlighn, T.S. Schorn, G.J. Zingaro, P.K.S. Siegl, J.Med. chem.36 (1993) 3207-containing 3210 (f) M.M. Aly, Y.A. Mohamed, K. A. El-Bayouki, W. M. Basyouni, S. Y. Abbas, Eur. J. Med. Chem. 45 (2010) 3365−3373; (g) S. Kobayashi, M. Ueno, R. Suzuki and H. Ishitani, Tetrahedron Lett. 40 (1999) 2175−2178; (h) S. L. Cao, Y. P. Feng, Y. Y. Jiang, S. Y. Liu, G. Y. Ding, R. T. Li, Bioorg. Med. Chem. Lett. 15 (2005) 1915−1917; (i) D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 103 (2003) 893−930; (j) T. Hisano, M. Ichikawa, A. Nakagawa, M. Tsuji, Chem. Pharm. Bull. 23 (1975) 1910−1916; (k) R. J. Abdel-Jalil, H. M. Aldoqum, M. T. Ayoub, W. Voelter, Heterocycles 65 (2005) 2061−2070; (l) Y. Mitobe, S. Ito, T. Mizutani, T. Nagase, N. Sato, S. Tokita, Bioorg. Med. Chem. Lett. 19 (2009) 4075−4078; (m) K. Juvale, M. Wiese, Bioorg. Med. Chem. Lett. 22 (2012) 6766−6769; (n) C. Balakumar, P. Lamba, D. P. Kishore, B. L. Narayana, K. V. Rao, K. Rajwinder, A. R. Rao, B. Shireesh, B. Narsaiah, Eur. J. Med. Chem. 45 (2010) 4904−4913; (o) D. Zhan, T. Li, H. Wei, W. Weng, K. Ghandi, Q. Zeng, RSC Adv. 3 (2013) 9325−9329.）
In recent years, with the idea of green chemical atom economy, the use of transition metal catalysts to catalyze organic reactions has received much attention. Among them, the acceptor-free dehydrogenation reaction catalyzed by a transition metal catalyst is an important method for preparing quinazolinone. 2011, Zhou et al reported an iridium catalyst [ Cp IrCl ]2]2A method for catalytically synthesizing quinazolinone. The method selects anthranilamide and primary alcohol as raw materials, quinazolinone is obtained with high yield under the action of a catalyst, and H is generated in the reaction process2And H2O is the only by-product. In 2015, Li research groups utilized water-soluble catalysts [ Cp Ir (H)2O)3][OTf]2The quinazolinone is successfully prepared in an aqueous phase by selecting anthranilamide and aldehyde as reactants. Compared with the report of Zhou et al, the method selects water as the solvent to replace the traditional organic solvent, and better meets the requirement of green chemistry. ((a) A. Corma, J. Navas, M.J. Sabater, chem. Rev. 12 (2019)) 3642-ng, J. Am. Chem. Soc. 134 (2013) 12474−12477; (c) J. W. Liu, J. Yang, C. Schneider, R. Franke, R. Jackstell, M. Beller, Angew. Chem. Int. Ed. 59 (2020) 9032−9040; (d) C. Gnanaprakasam, D. Milstein, Science 341 (2013) 1229712; (e) F. Li, L. Lu, P. C. Liu, Org. Lett. 18 (2016) 2580−2583; (f) J. Zhou, J. Fang, J. Org. Chem. 76 (2011) 7730−7736; (g) F. Li, L. Lu, J. Ma, Org. Chem. Front. 2 (2015) 1589−1597.）
Although the synthesis of quinazolinones by transition metal catalyzed processes avoids the formation of by-products and improves the atom economy of the reaction, the use of transition metals is inevitably required. Transition metals such as Ir, Ru, and Rh are not only low in reserves on the earth but also expensive, and bring about a certain influence in the separation and purification of products.
Therefore, from the perspective of green organic synthesis, the development of a method for synthesizing quinazolinone under the catalysis of a nonmetal catalyst under mild conditions has important research value and scientific significance.
Disclosure of Invention
The invention aims to provide a method for synthesizing quinazolinone through photocatalysis, which is characterized in that the method synthesizes quinazolinone through photocatalysis, does not use nonmetal catalysis, has mild reaction conditions, simple operation and environmental protection, and provides a new idea for the synthesis of quinazolinone.
The invention is realized by the following technical scheme:
the quinazolinone provided by the invention has a structure shown in the following formula I:
Figure 933432DEST_PATH_IMAGE001
the method for synthesizing the quinazolinone shown in the formula I comprises the step of obtaining the quinazolinone shown in the formula I through the photocatalytic reaction of anthranilamide shown in the formula II and aldehyde shown in the formula III; the reaction formula is as follows:
Figure 805442DEST_PATH_IMAGE002
。
further, in the above formula I, formula II and formula III, R1Selected from hydrogen, methyl or halogen; r2Selected from phenyl, methylphenyl, 3, 4-dimethylphenyl, isopropylphenyl, methoxyphenyl, halophenyl, hydroxyphenyl, cyanophenyl, trifluoromethylphenyl, pyridyl, furyl, naphthyl, phenethyl, cinnamyl, cyclohexenyl, nonyl, cyclohexyl or methyl; r3Selected from hydrogen, methyl or phenyl.
Furthermore, the photocatalytic reaction refers to that the anthranilamide and aldehyde are subjected to cyclization oxidation reaction under the induction of visible light to obtain quinazolinone. In the photocatalytic reaction, fluorescein is used as a photocatalyst, p-toluenesulfonic acid is used as an auxiliary catalyst, and the photocatalytic reaction is carried out under the irradiation of blue light. The structure of fluorescein is shown below:
Figure 422369DEST_PATH_IMAGE003
further, the molar ratio of anthranilamide to aldehyde is 1: 1.
Further, the photocatalyst is used in an amount of 1 to 3mol%, preferably 2 to 3mol%, based on the anthranilamide.
Further, the p-toluenesulfonic acid is used in an amount of 10 to 30%, preferably 10%, based on the molar amount of anthranilamide.
Further, the blue light can be realized by a blue light lamp, and the power of the blue light lamp is 5-15 w.
Further, the photocatalytic reaction is carried out in the presence of a solvent. The solvent is used for providing a reaction environment, and organic solvents such as acetonitrile, toluene, tetrahydrofuran or ethanol can be selected. The choice of different solvents has an influence on the yield of the reaction, the preferred solvent being acetonitrile. The amount of the solvent may be adjusted as necessary.
Further, in the step (1), the reaction temperature is room temperature, and the reaction time is 2-3 h.
In one embodiment of the present invention, a specific procedure for the synthesis of quinazolinone is provided as follows: mixing anthranilamide, aldehyde, photocatalyst, p-toluenesulfonic acid and solvent, and reacting the obtained mixture under the irradiation of a 5-15W blue light lamp to obtain quinazolinone.
The invention selects fluorescein as a photocatalyst, and the quinazolinone is synthesized by the cyclization oxidation reaction of anthranilamide and aldehyde under the irradiation of blue light. Compared with the prior art, the method has the following remarkable advantages:
1) the non-metal catalyst is used, so that the reaction cost is reduced;
2) the reaction conditions are mild, and the reaction can be completed at room temperature;
3) simple operation, short reaction time, simple post-treatment, high product yield and more environmental protection.
4) The method not only has higher academic value, but also has certain industrialization prospect.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of the product of example 1.
FIG. 2 is a nuclear magnetic carbon spectrum of the product of example 1.
Detailed Description
The present invention is further illustrated by the following examples, which are intended to be purely exemplary and are not to be construed as limiting the scope of the invention. Many modifications, variations and changes in materials, methods and reaction conditions may be made simultaneously with respect to the disclosure herein. All such modifications, variations and changes are intended to fall within the spirit and scope of the present invention.
Example 1 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 978115DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (39.1 mg) with the melting point of 237-.
The nuclear magnetic spectrum of the product is shown in figures 1 and 2 and specifically as follows:
1H NMR (400 MHz, [D6]DMSO) δ 12.56 (br s, 1H), 8.19-8.15 (m, 3H), 7.84 (t, J = 7.5 Hz, 1H), 7.76 (d, J = 8.1 Hz, 1H), 7.59-7.51 (m, 4H); 13C NMR (100 MHz, [D6]DMSO) δ 162.3, 152.3, 148.8, 134.6, 131.4, 128.6, 127.8, 127.5, 126.6, 125.9, 121.0, 39.5.
example 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 373193DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (10.2 mg, 30 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (39.1 mg) with the melting point of 237-.
Example 3 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 279969DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (0.7 mg, 1 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (35.3 mg) with the melting point of 237-.
Example 4 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 903848DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (2.0 mg, 3 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (39.2 mg) with the melting point of 237-.
Example 5 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 641997DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 1 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (the volume ratio of developing agent to petroleum ether/ethyl acetate is =3: 1) as white solid (36.3 mg) with the melting point of 237-.
Example 6 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 207977DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture was reacted for 3h under the irradiation of a 10 w blue light lamp, after the reaction was completed, the solvent was removed by rotary evaporation, and then pure target compound was obtained as a white solid (39.2 mg) by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1), melting point 237-.
Example 7 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 602049DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and toluene (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (24.3 mg) with the melting point of 237-.
Example 8 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 91936DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and tetrahydrofuran (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (34.5 mg) with the melting point of 237-.
Example 9 2-phenyl-4-quinazolinone
2-Phenyl-4-quinazolinone
Figure 356695DEST_PATH_IMAGE004
Anthranilamide (27.2 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and ethanol (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (34.9 mg) with the melting point of 237-.
Example 10 2- (4-methylphenyl) -4- [3H ] quinazolinone
2-(p-Tolyl)quinazolin-4(3H)-one
Figure 906625DEST_PATH_IMAGE005
Anthranilamide (27.2 mg, 0.2 mmol), 4-methylbenzaldehyde (24.0 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (42.8 mg) with the melting point of 243-.
1H NMR (400 MHz, [D6]DMSO) δ 12.48 (br s, 1H), 8.15 (d, J = 7.8 Hz, 1H), 8.11 (d, J = 7.8 Hz, 2H), 7.82 (t, J = 7.5 Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.50 (t, J = 7.5 Hz, 1H), 7.36 (d, J = 7.8 Hz, 2H), 2.39 (s, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 162.3, 152.2, 148.9, 141.5, 134.6, 129.9, 129.2, 127.7, 127.5, 126.4, 125.9, 120.9, 21.0.
Example 112- (3, 4-dimethylphenyl) -4- [3H ] quinazolinone
2-(3,4-Dimethylphenyl)quinazolin-4(3H)-one
Figure 787994DEST_PATH_IMAGE006
Anthranilamide (27.2 mg, 0.2 mmol), 3, 4-dimethylbenzaldehyde (26.8 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound which is white solid (43.6 mg) and has the melting point of 239-241 ℃ is obtained by column chromatography (the volume ratio of developing agent to petroleum ether/ethyl acetate is =3: 1).
1H NMR (400 MHz, [D6]DMSO) δ 12.41 (br s, 1H), 8.15 (d, J = 7.8 Hz, 1H), 8.00 (s, 1H), 7.93 (d, J = 7.8 Hz, 1H), 7.82 (t, J = 7.5 Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.51 (t, J = 7.4 Hz, 1H), 7.30 (d, J = 7.8 Hz, 1H), 2.31 (d, J = 6.4 Hz, 6H); 13C NMR (100 MHz, [D6]DMSO) δ 162.3, 152.4, 148.9, 140.3, 136.6. 134.6, 130.2, 129.7, 128.6, 127.4, 126.4, 125.9, 125.2, 120.9, 19.46, 19.43.
Example 12 2- (4-methoxyphenyl) -4- [3H ] quinazolinone
2-(4-Methoxyphenyl)quinazolin-4(3H)-one
Figure 534102DEST_PATH_IMAGE007
Anthranilamide (27.2 mg, 0.2 mmol), 4-methoxybenzaldehyde (27.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of the developing agent to the petroleum ether to the ethyl acetate is =3: 1) as a white solid (44.8 mg) with the melting point of 246-247 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.43 (br s, 1H), 8.20 (d, J = 8.2 Hz, 2H), 8.14 (d, J = 7.7 Hz, 1H), 7.81 (t, J = 7.3 Hz, 1H), 7.71 (d, J = 8.0 Hz, 1H), 7.48 (t, J = 7.3 Hz, 1H), 7.10 (d, J = 8.2 Hz, 2H), 3.84 (s, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 162.4, 161.9, 152.0, 148.8, 134.6, 129.5, 127.2, 126.2, 125.9, 124.8, 120.7, 114.0, 55.5.
Example 13 2- (4-fluorophenyl) -4- [3H ] quinazolinone
2-(4-Fluorophenyl)quinazolin-4(3H)-one
Figure 184526DEST_PATH_IMAGE008
Anthranilamide (27.2 mg, 0.2 mmol), 4-fluorobenzaldehyde (24.8 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (a developing agent: petroleum ether/ethyl acetate volume ratio is =3: 1) and is a white solid (39.2 mg) with a melting point of 258-.
1H NMR (400 MHz, [D6]DMSO) δ 12.57 (br s, 1H), 8.25 (t, J = 6.7 Hz, 2H), 8.16 (d, J = 7.8 Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.75 (d, J = 8.1 Hz, 1H), 7.52 (t, J = 7.4 Hz, 1H), 7.40 (t, J = 8.5 Hz, 2H); 13C NMR (100 MHz, [D6]DMSO) δ 165.3 (d, J C-F = 248.0 Hz), 162.3, 151.4, 148.7, 134.7, 130.5 (d, J C-F = 9.0 Hz), 129.3 (d, J C-F = 2.8 Hz), 127.5, 126.7, 125.9, 120.9, 115.8 (d, J C-F = 21.8 Hz).
Example 14 2- (4-chlorophenyl) -4- [3H ] quinazolinone
2-(4-Fluorophenyl)quinazolin-4(3H)-one
Figure 843040DEST_PATH_IMAGE009
Anthranilamide (27.2 mg, 0.2 mmol), 4-chlorobenzaldehyde (28.1 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture was reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction was completed, the solvent was removed by rotary evaporation, and then pure target compound was obtained by column chromatography (developer: petroleum ether/ethyl acetate volume ratio =3: 1) as a white solid (43.7 mg) with melting point 185-186 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.65 (br s, 1H), 8.19 (d, J = 7.9 Hz, 1H), 7.86 (t, J = 7.6 Hz, 1H), 7.72 (d, J = 8.2 Hz, 1H), 7.68 (d, J = 7.5 Hz, 1H), 7.63-7.56 (m, 3H), 7.50 (t, J = 7.4 Hz, 1H); 13C NMR (100 MHz, [D6]DMSO) δ 161.4, 152.3, 148.6, 134.6, 133.8, 131.7, 131.5, 130.9, 129.6, 127.5, 127.3, 127.1, 125.9, 121.3.
Example 15 2- (3-bromophenyl) -4- [3H ] quinazolinone
2-(3-Bromophenyl)quinazolin-4(3H)-one
Figure 946126DEST_PATH_IMAGE010
Anthranilamide (27.2 mg, 0.2 mmol), 3-bromobenzaldehyde (37.0 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added in that order to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as a white solid (53.2 mg) with a melting point of 296-297 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.62 (br s, 1H), 8.37 (s, 1H), 8.17 (t, J = 9.3 Hz, 2H), 7.85 (t, J = 7.6 Hz, 1H), 7.78 (t, J = 9.1 Hz, 2H), 7.56-7.50 (m, 2H); 13C NMR (100 MHz, [D6]DMSO) δ 162.2, 151.0, 148.5, 135.0, 134.8, 134.1, 130.8, 130.4, 127.7, 127.0, 126.8, 125.9, 121.9, 121.2.
Example 16 2- (4-cyanophenyl) -4- [3H ] quinazolinone
4-(4-Oxo-3,4-dihydroquinazolin-2-yl)benzonitrile
Figure 230345DEST_PATH_IMAGE011
Anthranilamide (27.2 mg, 0.2 mmol), 4-cyanobenzaldehyde (26.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture was reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction was completed, the solvent was removed by rotary evaporation, and then pure target compound was obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as a white solid (44.8 mg) with a melting point of 281-.
1H NMR (400 MHz, [D6]DMSO) δ 12.76 (br s, 1H), 8.34 (d, J = 8.0 Hz, 2H), 8.18 (d, J = 7.8 Hz, 1H), 8.05 (d, J = 8.0 Hz, 2H), 7.87 (t, J = 7.4 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H), 7.57 (t, J = 7.4 Hz, 1H); 13C NMR (100 MHz, [D6]DMSO) δ 162.2, 151.0, 148.3, 136.9, 134.8, 132.6, 128.7, 127.7, 127.3, 126.0, 121.2, 118.4, 113.6.
Example 17 2- (2-pyridinyl) -4- [3H ] quinazolinone
2-(Pyridin-2-yl)quinazolin-4(3H)-one
Figure 797593DEST_PATH_IMAGE012
Anthranilamide (27.2 mg, 0.2 mmol), pyridine-2-carbaldehyde (21.4 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (a developing agent: petroleum ether/ethyl acetate volume ratio is =3: 1) and is white solid (37.2 mg) with the melting point of 144-146 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 11.87 (br s, 1H), 8.77 (d, J = 4.5 Hz, 1H), 8.47 (d, J = 7.9 Hz, 1H), 8.20 (d, J = 7.8 Hz, 1H), 8.08 (t, J = 7.7 Hz, 1H), 7.88 (t, J = 7.5 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.67 (t, J = 6.0 Hz, 1H), 7.58 (t, J = 7.4 Hz, 1H); 13C NMR (100 MHz, [D6]DMSO) δ 160.8, 150.0, 149.0, 148.7, 148.5, 138.0, 134.8, 127.8, 127.3, 126.6, 126.1, 122.2, 122.0.
Example 18 2- (1-naphthyl) -4- [3H ] quinazolinone
2-(Naphthalen-1-yl)quinazolin-4(3H)-one
Figure 830271DEST_PATH_IMAGE013
Anthranilamide (27.2 mg, 0.2 mmol), 1-naphthaldehyde (31.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (the volume ratio of developing agent to petroleum ether/ethyl acetate is =3: 1) and is white solid (48.1 mg) with the melting point of 286-.
1H NMR (400 MHz, [D6]DMSO) δ 12.70 (br s, 1H), 8.24-8.12 (m, 3H), 8.06 (d, J = 8.2 Hz, 1H), 7.87 (t, J = 7.6 Hz, 1H), 7.81 (d, J = 7.0 Hz, 1H), 7.75 (d, J = 8.1 Hz, 1H), 7.67-7.57 (m, 4H); 13C NMR (100 MHz, [D6]DMSO) δ 162.0, 153.8, 148.6, 134.6, 133.2, 131.7, 130.4, 130.3, 128.4, 127.7, 127.4, 127.1, 126.9, 126.4, 125.9, 125.3, 125.1, 121.2.
Example 19 2- (phenethyl) -4- [3H ] quinazolinone
2-Phenethylquinazolin-4(3H)-one
Figure 482969DEST_PATH_IMAGE014
Anthranilamide (27.2 mg, 0.2 mmol), phenylpropanal (26.8 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of the developing agent to the petroleum ether to the ethyl acetate is =3: 1) as a white solid (43.2 mg) with the melting point of 210-211 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.27 (br s, 1H), 8.09 (d, J = 7.8 Hz, 1H), 7.78 (t, J = 7.5 Hz, 1H), 7.63 (d, J = 8.1 Hz, 1H), 7.47 (t, J = 7.4 Hz, 1H), 7.28-7.19 (m, 5H), 3.05 (t, J = 7.8 Hz, 2H), 2.89 (t, J = 7.8 Hz, 2H); 13C NMR (100 MHz, [D6]DMSO) δ 161.8, 156.6, 148.9, 140.8, 134.4, 128.4, 128.4, 126.9, 126.1, 126.1, 125.7, 120.9, 36.4, 32.5.
Example 20 2- (3-cyclohexenyl) -4- [3H ] quinazolinone
2-(Cyclohex-3-en-1-yl)quinazolin-4(3H)-one
Figure 56033DEST_PATH_IMAGE015
Anthranilamide (27 mg, 0.2 mmol), 1,2,3, 6-tetrahydrobenzaldehyde (22 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of the developing agent to the petroleum ether to the ethyl acetate is =3: 1) as a white solid (38.5 mg) with the melting point of 236-238 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.18 (br s, 1H), 8.09 (d, J = 7.8 Hz, 1H), 7.77 (t, J = 7.6 Hz, 1H), 7.61 (d, J = 8.1 Hz, 1H), 7.46 (t, J = 7.5 Hz, 1H), 5.76-5.70 (m, 2H), 2.79-2.77 (m, 1H), 2.43-2.25 (m, 2H), 2.13-1.99 (m, 3H), 1.79-1.68 (m, 1H); 13C NMR (100 MHz, [D6]DMSO) δ 162.4, 160.9, 149.3, 134.8, 127.5, 127.0, 126.5, 126.2, 121.4, 29.1, 27.1, 25.2.
Example 21 2- (nonyl) -4- [3H ] quinazolinone
2-Nonylquinazolin-4(3H)-one
Figure 212208DEST_PATH_IMAGE016
Anthranilamide (27.2 mg, 0.2 mmol), decanal (28.4 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (the volume ratio of developing agent to petroleum ether/ethyl acetate is =3: 1) as white solid (45.3 mg) with the melting point of 150-.
1H NMR (400 MHz, [D6]DMSO) δ 121.17 (br s, 1H), 8.08 (d, J = 7.8 Hz, 1H), 7.76 (t, J = 7.6 Hz, 1H), 7.59 (d, J = 8.2 Hz, 1H), 7.44 (t, J = 7.5 Hz, 1H), 2.58 (t, J = 7.5 Hz, 2H), 1.72-1.67 (m, 2H), 1.28-1.22 (m, 12H), 0.83 (t, J = 5.9 Hz, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 161.9, 157.5, 149.0, 134.3, 126.8, 128.9, 125.7, 120.8, 34.5, 31.3, 28.9, 28.8, 28.7, 28.6, 26.8, 22.1, 14.0.
Example 22 2- (cyclohexyl) -4- [3H ] quinazolinone
2-Cyclohexylquinazolin-4(3H)-one
Figure 461792DEST_PATH_IMAGE017
Anthranilamide (27.2 mg, 0.2 mmol), cyclohexylformaldehyde (22.4 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (a developing agent: petroleum ether/ethyl acetate volume ratio is =3: 1) as a white solid (37.8 mg) with a melting point of 150-.
1H NMR (400 MHz, [D6]DMSO) δ 12.09 (br s, 1H), 8.08 (d, J = 7.8 Hz, 1H), 7.75 (t, J = 7.6 Hz, 1H), 7.60 (d, J = 8.1 Hz, 1H), 7.44 (t, J = 7.4 Hz, 1H), 2.56 (t, J = 11.7 Hz, 1H), 1.91-1.88 (m, 4H), 1.65-1.53 (m, 3H), 1.34-1.19 (m, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 162.0, 160.8, 149.0, 134.3, 127.0, 126.0, 125.7, 121.0, 42.9, 30.2, 25.6, 25.4.
Example 23 2- (methyl) -4- [3H ] quinazolinone
2-Methylquinazolin-4(3H)-one
Figure 336207DEST_PATH_IMAGE018
Anthranilamide (27.2 mg, 0.2 mmol), aqueous acetaldehyde (40%) (22.0 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then pure target compound is obtained by column chromatography (developing solvent: petroleum ether/ethyl acetate volume ratio =3: 1) as white solid (27.1 mg) with the melting point of 238-.
1H NMR (400 MHz, [D6]DMSO) δ 12.20 (br s, 1H), 8.07 (d, J = 7.6 Hz, 1H), 7.78-7.74 (m, 1H), 7.57 (d, J = 7.9 Hz, 1H),7.46-7.43 (m, 1H), 2.34 (s, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 161.7, 154.3, 149.0, 134.3, 126.6, 125.9, 125.7, 120.7, 21.5.
Example 24 7-methyl-2-phenyl-4- [3H ] quinazolinone
7-Methyl-2-phenylquinazolin-4(3H)-one
Figure 712962DEST_PATH_IMAGE019
2-amino-4-methylbenzamide (30.0 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-methylbenzenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were sequentially added to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of the developing agent to the petroleum ether to the ethyl acetate is =3: 1) and is a white solid (39.3 mg) with the melting point of 205-207 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.46 (br s, 1H), 8.17 (d, J = 7.6 Hz, 2H), 8.04 (d, J = 8.0 Hz, 1H), 7.59-7.52 (m, 4H), 7.35 (d, J = 8.1 Hz, 1H), 2.47 (s, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 162.1, 152.4, 148.9, 145.2, 132.8, 131.4, 128.7, 128.1, 127.8, 127.2, 125.8, 118.6, 21.4.
Example 25 6-fluoro-2-phenyl-4- [3H ] quinazolinone
6-Fluoro-2-phenylquinazolin-4(3H)-one
Figure 192485DEST_PATH_IMAGE020
2-amino-6-fluorobenzamide (30.8 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added in this order to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of developing agent to petroleum ether/ethyl acetate is =3: 1) as a white solid (41.6 mg) with the melting point of 277-.
1H NMR (400 MHz, [D6]DMSO) δ 12.67 (br s, 1H), 8.17 (d, J = 7.6 Hz, 2H), 7.81 (m, 2H), 7.72 (t, J = 8.7 Hz, 1H), 7.59-7.53 (m, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 161.7, 161.2 (d, J C-F = 240.0 Hz), 151.9, 145.7, 132.6, 131.5, 130.4 (d, J C-F = 8.2 Hz), 128.7, 127.8, 123.2 (d, J C-F = 23.9 Hz), 122.3 (d, J C-F = 8.3 Hz), 110.7 (d, J C-F = 23.2 Hz).
Example 26 chloro-2-phenyl-4- [3H ] quinazolinone
7-Chloro-2-phenylquinazolin-4(3H)-one
Figure 629283DEST_PATH_IMAGE021
2-amino-7-chlorobenzamide (34.1 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture was reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction was completed, the solvent was removed by rotary evaporation, and then pure target compound was obtained as a white solid (46.2 mg) by column chromatography (developer: petroleum ether/ethyl acetate volume ratio =3: 1) with melting point 279-287 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 12.68 (br s, 1H), 8.17-8.12 (m, 3H), 7.77 (s, 1H), 8.60-8.52 (m, 4H); 13C NMR (100 MHz, [D6]DMSO) δ 161.7, 153.8, 149.9, 139.2, 132.4, 131.8, 128.7, 128.0, 128.0, 126.8, 126.6, 119.8.
Example 27 3-methyl-2-phenyl-4- [3H ] quinazolinone
3-Methyl-2-phenylquinazolin-4(3H)-one
Figure 709103DEST_PATH_IMAGE022
2-amino-N-methylbenzamide (30.0 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-methylbenzenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were sequentially added to a 15 mL reaction tube. The reaction mixture is reacted for 2 hours under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of the developing agent to the petroleum ether to the ethyl acetate is =3: 1) and is a white solid (41.3 mg) with the melting point of 112-114 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 8.20 (d, J = 7.5 Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.69 (m, 3H), 7.56-7.55 (m, 4H), 3.36 (s, 3H); 13C NMR (100 MHz, [D6]DMSO) δ 161.7, 156.2, 147.1, 135.4, 134.4, 129.8, 128.4, 128.3, 127.2, 126.9, 126.1, 120.2, 33.9.
Example 28 diphenyl-4- [3H ] quinazolinone
2,3-diphenylquinazolin-4(3H)-one
Figure 889549DEST_PATH_IMAGE023
2-amino-N-phenylbenzamide (42.4 mg, 0.2 mmol), benzaldehyde (21.2 mg, 0.2 mmol), fluorescein (1.3 mg, 2 mol%), p-toluenesulfonic acid (3.4 mg, 10 mol%) and acetonitrile (2 mL) were added sequentially to a 15 mL reaction tube. The reaction mixture is reacted for 2 h under the irradiation of a 10 w blue light lamp, after the reaction is finished, the solvent is removed by rotary evaporation, and then the pure target compound is obtained by column chromatography (the volume ratio of the developing agent to the petroleum ether to the ethyl acetate is =3: 1) as a white solid (52.8 mg) with the melting point of 158-159 ℃.
1H NMR (400 MHz, [D6]DMSO) δ 8.21 (d, J = 7.9 Hz, 1H), 7.90 (t, J = 7.6 Hz, 1H), 7.78 (d, J = 8.1 Hz, 1H), 7.61 (t, J = 7.5 Hz, 1H), 7.38-7.21 (m, 10H); 13C NMR (100 MHz, [D6]DMSO) δ 161.4, 155.2, 147.3, 137.9, 135.7, 134.9, 129.6, 128.9, 128.9, 128.6, 128.2, 127.5, 127.4, 127.2, 126.5, 120.8.
Comparative example 1
2-phenyl-4-quinazolinone was prepared in the manner of example 1, except that: p-toluenesulfonic acid was not used. After the reaction, a white solid was obtained with a mass of 6.9 mg.

Claims (9)

1. A method for synthesizing quinazolinone through photocatalysis is characterized in that: the method comprises the steps of carrying out a photocatalytic reaction on anthranilamide shown in a formula II and aldehyde shown in a formula III to obtain quinazolinone shown in a formula I;
Figure 378506DEST_PATH_IMAGE001
。
2. according to the claimsThe method of claim 1, comprising: in the formulae I, II and III, R1Selected from hydrogen, methyl or halogen; r2Selected from phenyl, methylphenyl, 3, 4-dimethylphenyl, isopropylphenyl, methoxyphenyl, halophenyl, hydroxyphenyl, cyanophenyl, trifluoromethylphenyl, pyridyl, furyl, naphthyl, phenethyl, cinnamyl, cyclohexenyl, nonyl, cyclohexyl or methyl; r3Selected from hydrogen, methyl or phenyl.
3. A method according to claim 1 or 2, characterized by: the fluorescein is used as a photocatalyst, and the p-toluenesulfonic acid is used as an auxiliary catalyst to perform photocatalytic reaction under the irradiation of blue light.
4. The method of claim 3, wherein: the dosage of the photocatalyst is 1-3 mol% of anthranilamide, preferably 2-3 mol%; the dosage of the p-toluenesulfonic acid is 10-30% of the molar weight of the anthranilamide.
5. A method according to claim 1 or 3, characterized by: the power of the blue light is 5-15 w.
6. A method according to claim 1 or 3, characterized by: the molar ratio of anthranilamide to aldehyde was 1: 1.
7. A method according to claim 1 or 3, characterized by: the reaction is carried out in the presence of a solvent, which is acetonitrile, toluene, tetrahydrofuran or ethanol.
8. The method according to any of claims 1-7, characterized by the following specific steps: mixing anthranilamide, aldehyde, photocatalyst, p-toluenesulfonic acid and solvent, and reacting the obtained mixture under the irradiation of a 5-15W blue light lamp to obtain quinazolinone.
9. The method of claim 1, 3 or 8, wherein: in the step (1), the reaction temperature is room temperature, and the reaction time is 1-3 h.
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CN113698358A (en) * 2021-08-27 2021-11-26 武汉理工大学 Method for synthesizing quinazolinone compound under induction of visible light
CN113698358B (en) * 2021-08-27 2024-01-16 武汉理工大学 Method for synthesizing quinazolinone compound by visible light induction
CN114989094A (en) * 2022-04-12 2022-09-02 云南民族大学 Method for synthesizing benzimidazole derivative by visible light catalysis
CN114989094B (en) * 2022-04-12 2023-09-29 云南民族大学 Method for synthesizing benzimidazole derivative by visible light catalysis

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