A method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazolin 12-one compounds

Abstract

This invention provides a method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds, relating to the field of organic synthesis technology. The method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds provided by this invention includes the following steps: mixing a 2-aminobenzamide compound, a phenyl 2-iodoisothiocyanate compound, a catalyst, and a polar organic solvent, and performing a coupling addition reaction to obtain 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds. The preparation method provided by this invention has the advantages of simple process, mild conditions, no use of oxidants, and good functional group tolerance.

Description

Technical Field

[0001] This invention relates to the field of organic synthesis technology, specifically to a method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds. Background Technology

[0002] N and S-containing heterocyclic compounds have wide applications in medicinal chemistry, agricultural chemistry, and materials science. Among them, 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds are a special class of scaffolds with diverse biological and pharmacological activities, as well as optical and electronic activities. For example, compound (I) showed epidermal growth factor receptor (EGFR) inhibitory activity in the human breast adenocarcinoma cell line (MCF-7). Due to their good biological activity and synthetic applications, the construction of 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-ones has attracted great attention in recent years.

[0003]

[0004] Currently, the main methods for synthesizing 12H-benzo[4,5]thiazo[2,3-b]quinazolin-12-one derivatives are:

[0005] (a) Mei-Lin Liu et al. (Mei-Lin Liu, et al. "Synthesis of Pyrido-Fused Quinazolinone Derivatives via Copper-Catalyzed Domino Reaction." 2016, 18, 824-827. DOI: 10.1021 / acs.orglett.6b00113.) reported the formation of 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one from indigo and 2-bromobenzothiazole in the presence of copper acetate and sodium bicarbonate, for example:

[0006]

[0007] (b) Chuthamat Duangkamol et al. (Chuthamat Duangkamol, et al. Potassium Periodate Mediated Oxidative Cyclodesulfurization toward Benzofused Nitrogen Heterocycles. Synthesis. 2020, 52, 1981-1990. DOI: 10.1055 / s-0039-1690855) reported the formation of 12H-benzo[4,5]thiazo[2,3-b]quinazolin-12-one by oxidation of 2-aminobenzylthiophenol and methyl 2-isothiocyanate with potassium carbonate and periodic acid, for example:

[0008]

[0009] (c) Zhi-Wen Zhou et al. (Jia, Feng-Cheng, Xu, Cheng, Jiang, Shi-Fen. Concise construction of 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones via anunusual TBHP / Na2CO3 promoted cascade oxidative cyclization and interrupted Dimroth rearrangement. Chem. Commun. 2017, 53, 1056-1059. DOI:10.1039 / c6cc09376k.) discovered that indigo and phenyl 2-haloisothiocyanate, under the oxidation of TBHP and catalysis of sodium carbonate, generate 12H-benzo[4,5]thiazolo[2,3-b]quinazolin-12-ones, for example:

[0010]

[0011] However, the above methods still have drawbacks such as complex processes, the need for oxidants, limited substrate range, and high reaction temperatures. Summary of the Invention

[0012] The purpose of this invention is to provide a method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds. The preparation method provided by this invention has the advantages of simple process, mild conditions, no use of oxidants and good functional group tolerance.

[0013] To achieve the above objectives, the present invention provides the following technical solution:

[0014] This invention provides a method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds, comprising the following steps:

[0015] A 2-aminobenzamide compound, a 2-iodophenyl isothiocyanate compound, a catalyst, and a polar organic solvent were mixed and subjected to a coupling addition reaction to obtain a 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compound.

[0016] The 2-aminobenzamide compounds have the structure shown in Formula I:

[0017]

[0018] The 2-iodophenyl isothiocyanate compound has the structure shown in Formula II:

[0019]

[0020] The 12H-benzo[4,5]thiazo[2,3-b]quinazolin 12-one compounds have the structure shown in Formula III:

[0021]

[0022] In Equations I and III include

[0023]

[0024] The number of R1 groups is 1 to 4; the R1 groups are electron-donating or electron-withdrawing groups.

[0025] The number of R2 groups is 1 to 4; the R2 groups are electron-donating or electron-withdrawing groups.

[0026] Preferably, R1 comprises one or more of hydrogen, alkyl, alkoxy, and halogen groups;

[0027] The R2 includes one or more of hydrogen, alkyl, alkoxy, and halogen groups.

[0028] Preferably, the 2-aminobenzamide compounds include one or more of 2-aminobenzamide, 2-amino-3-methylbenzamide, 2-amino-4-methylbenzamide, 2-amino-5-methylbenzamide, 2-amino-5-methoxybenzamide, 2-amino-4-fluorobenzamide, 2-amino-3-bromobenzamide, 2-amino-5-bromobenzamide, 2-amino-4-chlorobenzamide, 2-amino-5-chlorobenzamide, 3-aminothiophene-2-carboxamide, and 3-amino-2-naphthylcarboxamide;

[0029] The 2-iodophenyl isothiocyanate compounds include one or more of the following: 2-iodophenyl isothiocyanate, 2-iodo-1-thioisocyanate-4-methylbenzene, 1-iodo-2-thioisocyanate-4-methylbenzene, 2-iodo-1-thioisocyanate-4-methoxybenzene, 1-iodo-2-thioisocyanate-4-methoxybenzene, 1-chloro-2-iodo-3-thioisocyanate, 4-chloro-1-iodo-2-thioisocyanate, 4-bromo-2-iodo-1-thioisocyanate, 4-bromo-1-iodo-2-thioisocyanate, 4-fluoro-2-iodo-1-thioisocyanate, 4-fluoro-1-iodo-2-thioisocyanate, and 5-chloro-1-fluoro-3-iodo-2-thioisocyanate.

[0030] Preferably, the molar ratio of the 2-aminobenzamide compound and the 2-iodophenyl isothiocyanate compound is 1:1.

[0031] Preferably, the catalyst comprises a copper-containing compound.

[0032] Preferably, the copper-containing compound includes one or more of copper acetate, copper chloride, copper bromide, copper trifluoromethanesulfonate, cuprous chloride, and cuprous bromide.

[0033] Preferably, the molar ratio of the 2-aminobenzamide compound to the catalyst is 1:0.2 to 0.5.

[0034] Preferably, the polar organic solvent includes dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, or toluene.

[0035] Preferably, the ratio of the polar organic solvent to the 2-aminobenzamide compound is 1L:0.1-0.2mol.

[0036] Preferably, the temperature of the coupling addition reaction is 80–130°C, and the time of the coupling addition reaction is 1–12 h.

[0037] This invention provides a method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds. The method offers advantages such as mild and easily controllable conditions, high reaction efficiency, readily available and inexpensive raw materials, and the absence of oxidizing agents. The prepared 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds exhibit high purity (98.5–99.9%), making them highly valuable for market application. Compared to multi-step synthetic reactions, this invention achieves the target product in a single step with a yield of 92%, demonstrating high reaction efficiency and cost-effectiveness. Detailed Implementation

[0038] This invention provides a method for preparing 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds, comprising the following steps:

[0039] A 2-aminobenzamide compound, a 2-iodophenyl isothiocyanate compound, a catalyst, and a polar organic solvent were mixed and subjected to a coupling addition reaction to obtain a 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compound.

[0040] The 2-aminobenzamide compounds have the structure shown in Formula I:

[0041]

[0042] The 2-iodophenyl isothiocyanate compound has the structure shown in Formula II:

[0043]

[0044] The 12H-benzo[4,5]thiazo[2,3-b]quinazolin 12-one compounds have the structure shown in Formula III:

[0045]

[0046] In Equations I and III include

[0047]

[0048] The number of R1 groups is 1 to 4; the R1 groups are electron-donating or electron-withdrawing groups.

[0049] The number of R2 groups is 1 to 4; the R2 groups are electron-donating or electron-withdrawing groups.

[0050] In this invention, unless otherwise specified, all raw materials used in the preparation are commercially available products well known to those skilled in the art.

[0051] In this invention, R1 preferably comprises one or more of hydrogen, alkyl, alkoxy, and halogen groups; R2 preferably comprises one or more of hydrogen, alkyl, alkoxy, and halogen groups. In this invention, the alkyl group in R1 and R2 independently comprises methyl; the alkoxy group in R1 and R2 independently comprises methoxy; and the halogen group in R1 and R2 independently comprises one or more of fluorine, bromine, and chloro groups.

[0052] In this invention, the 2-aminobenzamide compounds preferably include one or more of the following: 2-aminobenzamide, 2-amino-3-methylbenzamide, 2-amino-4-methylbenzamide, 2-amino-5-methylbenzamide, 2-amino-5-methoxybenzamide, 2-amino-4-fluorobenzamide, 2-amino-3-bromobenzamide, 2-amino-5-bromobenzamide, 2-amino-4-chlorobenzamide, 2-amino-5-chlorobenzamide, 3-aminothiophene-2-carboxamide, and 3-amino-2-naphthylcarboxamide.

[0053] In this invention, the 2-iodophenyl isothiocyanate compounds preferably include one or more of the following: 2-iodophenyl isothiocyanate, 2-iodo-1-thioisocyanate-4-methylbenzene, 1-iodo-2-thioisocyanate-4-methylbenzene, 2-iodo-1-thioisocyanate-4-methoxybenzene, 1-iodo-2-thioisocyanate-4-methoxybenzene, 1-chloro-2-iodo-3-thioisocyanate, 4-chloro-1-iodo-2-thioisocyanate, 4-bromo-2-iodo-1-thioisocyanate, 4-bromo-1-iodo-2-thioisocyanate, 4-fluoro-2-iodo-1-thioisocyanate, 4-fluoro-1-iodo-2-thioisocyanate, and 5-chloro-1-fluoro-3-iodo-2-thioisocyanate. In a specific embodiment of the present invention, the 2-iodoisothiocyanate phenyl ester compound is preferably prepared with reference to "Pinapati, S.; Mandapati, U.; Rudraraju, RRIron-Mediated Desulphurization Towards the Synthesis of 2-Halo Aromatic Isothiocyanates[J]. Chemistry Select. 2017, 2(1), 295-299."

[0054] In this invention, the molar ratio of the 2-aminobenzamide compound and the 2-iodophenyl isothiocyanate compound is preferably 1:1.

[0055] In this invention, the catalyst preferably comprises a copper-containing compound; the copper-containing compound preferably comprises one or more of copper acetate, copper chloride, copper bromide, copper trifluoromethanesulfonate, cuprous chloride, and cuprous bromide. In this invention, the molar ratio of the 2-aminobenzamide compound to the catalyst is preferably 1:0.2 to 0.5, more preferably 1:0.2.

[0056] In this invention, the polar organic solvent preferably includes dimethyl sulfoxide (DMSO), N,N-dimethylformamide, N,N-dimethylacetamide, or toluene. In this invention, the preferred molar ratio of the polar organic solvent to the 2-aminobenzamide compound is 1 L: 0.1–0.2 mol.

[0057] The present invention does not have any particular limitations on the mixing process of the 2-aminobenzamide compounds, 2-iodophenyl isothiocyanate compounds, catalysts and polar organic solvents. The materials can be mixed evenly according to a process known in the art.

[0058] In this invention, the temperature of the coupling addition reaction is preferably 80–130°C, more preferably 100°C; the time of the coupling addition reaction is preferably 1–12 h, more preferably 1 h. In this invention, the coupling addition reaction is preferably carried out under stirring conditions. This invention does not have a particular limitation on the stirring rate; any process well-known in the art can be followed to ensure the reaction proceeds smoothly. In this invention, the atmosphere for the coupling addition reaction is preferably an air atmosphere.

[0059] Following the coupling addition reaction, the present invention preferably includes purifying the resulting reaction system. In this invention, the purification method is preferably column chromatography, and the eluent used for column chromatography is preferably a mixed solvent of petroleum ether and ethyl acetate; the volume ratio of petroleum ether to ethyl acetate in the mixed solvent is preferably 1–10:1, more preferably 1–5:1. The present invention does not impose any special limitations on the specific process of the column chromatography; any method well known to those skilled in the art can be used. The present invention utilizes petroleum ether and ethyl acetate as eluents for purification, which can obtain the target compound with high purity.

[0060] In this invention, the 12H-benzo[4,5]thiazo[2,3-b]quinazolin 12-one compounds preferably include:

[0061]

[0062] In this invention, the purity of the 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compound is preferably 98.5-99.9%, and the yield is preferably 16-95%.

[0063] The technical solutions of this invention will be clearly and completely described below with reference to the embodiments thereof. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. All other embodiments obtained by those skilled in the art based on the embodiments of this invention without creative effort are within the scope of protection of this invention.

[0064] Example 1

[0065] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0066]

[0067] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 92% and a purity of 99.9%.

[0068] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0069] 1 H NMR (400MHz, CDCl3, ppm) δ8.97(d,J=9.2Hz,1H),8.38(d,J=9.3Hz,1H),7.76(t,J=8.4Hz,1H),7.60(dd,J=18.9,8.6Hz,2H),7.47-7.37(m,J=20Hz,3H);

[0070] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.70,156.91,147.17,136.07,134.84,127.11,126.77,126.67,125.90,125.79,123.71,121.74,119.23,118.58;

[0071] MS(EI,70eV)m / z 252,224,198,192,179.

[0072] Example 2

[0073] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0074]

[0075] 0.1 mmol of 2-amino-3-methylbenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 90% and a purity of 99.9%.

[0076] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0077] 1 H NMR (400MHz, CDCl3, ppm) δ8.96 (d, J = 8.1Hz, 1H), 8.22 (d, J = 7.9Hz, 1H), 7.57 (d, J = 7.0Hz, 2H), 7.47-7.34 (m, 2H), 7.30 (t, J = 7.6Hz, 1H), 2.59 (s, 3H);

[0078] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ161.07,155.53,145.91,136.05,135.28,134.4 3,126.64,126.53,125.28,124.69,123.91,121.67,119.21,118.45,17.54;

[0079] MS(EI,70eV)m / z 266,251,237,210,179.

[0080] Example 3

[0081] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0082]

[0083] 0.1 mmol of 2-amino-4-methylbenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 66% and a purity of 99.9%.

[0084] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0085] 1 H NMR (400MHz, CDCl3, ppm) δ9.02 (s, 1H), 8.30 (s, 1H), 7.62 (s, 1H), 7.51-7.40 (m, 3H), 7.29 (d, J = 7.8Hz, 1H), 2.52 (s, 3H);

[0086] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.7,156.1,147.3,146.1,136.2,127.5,126.9,126.7,126.6,125.6,123.7,121.7,119.2,116.2,22.1;

[0087] MS(EI,70eV)m / z 266,251,237,223,210.

[0088] Example 4

[0089] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0090]

[0091] 0.1 mmol of 2-amino-5-methylbenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 89% and a purity of 99.9%.

[0092] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0093] 1 H NMR (400MHz, CDCl3, ppm) δ8.88 (d, J = 8.9Hz, 1H), 8.06 (s, 1H), 7.52-7.42 (m, 3H), 7.39-7.28 (m, 2H), 2.42 (s, 3H);

[0094] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.72,155.91,145.21,136.34,136.12,135.9 4,126.66,126.57,126.38,125.67,123.76,121.70,119.22,118.28,21.30;

[0095] MS(EI,70eV)m / z 266,237,179,133,125.

[0096] Example 5

[0097] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0098]

[0099] 0.1 mmol of 2-amino-5-methoxybenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 84% and a purity of 99.9%.

[0100] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0101] 1 H NMR (400MHz, CDCl3, ppm) δ8.91 (d, J = 8.1Hz, 1H), 7.65 (s, 1H), 7.55-7.48 (m, 2H), 7.43-7.27 (m, 3H), 3.88 (s, 3H);

[0102] 13 C{ 1H}NMR (100MHz, CDCl3, ppm) δ160.56,157.57,154.29,141.91,135.97,127.4 2,126.64,126.62,125.28,123.93,121.71,119.21,119.16,106.03,55.81;

[0103] MS(EI,70eV)m / z 282,267,239,211,184.

[0104] Example 6

[0105] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0106]

[0107] 0.1 mmol of 2-amino-4-chlorobenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 95% and a purity of 99.9%.

[0108] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0109] 1 H NMR (400MHz, CDCl3, ppm) δ8.98 (d, J = 9.0Hz, 1H), 8.33 (d, J = 8.6Hz, 1H), 7.63 (d, J = 7.9Hz, 2H), 7.53-7.40 (m, 3H);

[0110] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.05,158.38,148.02,141.15,135.90,128.53,126.97,126.91,126.43,125.46,123.63,121.84,119.27,116.99;

[0111] MS(EI,70eV)m / z 286,258,251,223,196.

[0112] Example 7

[0113] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0114]

[0115] 0.1 mmol of 2-amino-5-chlorobenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 95% and a purity of 99.9%.

[0116] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0117] 1 H NMR (400MHz, CDCl3, ppm) δ9.00 (d, J = 7.7Hz, 1H), 8.37 (d, J = 2.2Hz, 1H), 7.71 (dd, J = 8.7, 2.5Hz, 1H), 7.62 (t, J = 9.7Hz, 2H), 7.53-7.43 (m, 2H);

[0118] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ159.54,157.21,145.63,135.79,135.20,131.41,127.53,126.94,126.91,126.32,123.68,121.80,119.50,119.27;

[0119] MS(EI,70eV)m / z 286,258,232,223,196.

[0120] Example 8

[0121] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0122]

[0123] 0.1 mmol of 2-amino-5-bromobenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 86% and a purity of 99.9%.

[0124] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0125] 1 H NMR (400MHz, CDCl3, ppm) δ8.96 (d, J = 8.5Hz, 1H), 8.50 (d, J = 2.2Hz, 1H), 7.86-7.80 (m, 1H), 7.62 (d, J = 7.6Hz, 1H), 7.54-7.41 (m, 3H);

[0126] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.61,156.87,147.11,136.01,134.78,127.07,126.72,126.62,125.86,125.75,123.67,121.70,119.17,118.53;

[0127] MS(EI,70eV)m / z 331,302,251,223,196.

[0128] Example 9

[0129] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0130]

[0131] 0.1 mmol of 2-amino-3-bromobenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 74% and a purity of 99.9%.

[0132] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0133] 1 H NMR (400MHz, CDCl3, ppm) δ8.96(s,1H),8.36(s,1H),8.04(s,1H),7.65(s,1H),7.48(s,2H),7.31(s,1H);

[0134] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.12,158.08,145.04,138.43,135.71,126.99,126.94,126.75,126.09,123.91,121.88,120.69,120.00,119.24;

[0135] MS(EI,70eV)m / z 331,251,223,196,191.

[0136] Example 10

[0137] The 12H-benzo[4,5]thiazo[2,3-b]quinazolin-12-one compound obtained in this example has the following structure:

[0138]

[0139] 0.1 mmol of 2-amino-4-fluorobenzamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 80% and a purity of 99.9%.

[0140] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0141] 1 H NMR (400MHz, CDCl3, ppm) δ8.93 (d, J = 8.1Hz, 1H), 8.41-8.35 (m, 1H), 7.60 (d, J = 7. 8Hz,1H),7.44(dt,J=22.4,7.0Hz,2H),7.29-7.23(m,1H),7.17(t,J=8.5Hz,1H);

[0142] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ168.04, 165.50, 159.84, 158.46, 149.21 (d, J = 13.0Hz), 135.87, 129.83 (d, J = 11 .0Hz), 126.86 (d, J = 22.0Hz), 123.50, 121.78, 119.20, 115.24, 114.69 (d, J = 24.0Hz), 111.16 (d, J = 11.0Hz);

[0143] MS(EI,70eV)m / z 270,251,242,223,216.

[0144] Example 11

[0145] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0146]

[0147] 0.1 mmol of 3-aminothiophene-2-carboxamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 59% and a purity of 99.9%.

[0148] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0149] 1 H NMR (400MHz, CDCl3, ppm) δ9.11 (s, 1H), 7.65 (s, 1H), 7.58 (s, 1H), 7.49 (dd, J = 15.2, 8.0Hz, 2H), 7.19 (s, 1H);

[0150] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ163.36,157.64,157.35,136.19,126.91,126.85,124.07,122.17,121.85,121.72,120.16,119.81;

[0151] MS(EI,70eV)m / z 258,225,204,198,192.

[0152] Example 12

[0153] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0154]

[0155] 0.1 mmol of 3-amino-2-naphthylcarboxamide, 0.1 mmol of phenyl 2-iodoisothiocyanate, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 16% and a purity of 99.9%.

[0156] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0157] 1 H NMR (400MHz, CDCl3, ppm) δ9.03 (s, 1H), 8.97 (d, J = 8.3Hz, 1H), 8.11-8.06 (m, 2H) ,7.97(d,J=8.3Hz,1H),7.63-7.57(m,2H),7.54-7.46(m,2H),7.43-7.39(m,1H);

[0158] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ161.07,156.07,142.41,136.98,136.16,130.90,129.47,12 9.11,128.80,127.89,126.84,126.55,126.06,123.50,123.13,121.79,118.94,117.95;

[0159] MS(EI,70eV)m / z 302,274,246,229,214.

[0160] Example 13

[0161] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0162]

[0163] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 2-iodo-1-thioisocyanate-4-methylbenzene, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 77% and a purity of 99.9%.

[0164] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0165] 1 H NMR (400MHz, CDCl3, ppm) δ8.79(d,J=8.5Hz,1H),8.37(d,J=8.0Hz,1H),7.74(t,J=7.6Hz,1H), 7.61(d,J=8.2Hz,1H),7.43(t,J=7.5Hz,1H),7.34(s,1H),7.20(d,J=8.5Hz,1H),2.37(s,3H);

[0166] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.49,157.04,147.19,136.95,134.67,133.8 0,127.63,127.03,125.86,125.67,123.60,121.86,118.81,118.57,21.29;

[0167] MS(EI,70eV)m / z 266,249,237,205,180.

[0168] Example 14

[0169] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0170]

[0171] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 1-iodo-2-thioisocyanate-4-methylbenzene, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 87% and a purity of 99.9%.

[0172] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0173] 1 H NMR (400MHz, CDCl3, ppm) δ8.76 (s, 1H), 8.34 (d, J = 7.3Hz, 1H), 7.72 (t, J = 7.6Hz, 1H), 7 .59(d,J=8.1Hz,1H),7.40(dd,J=15.7,7.8Hz,2H),7.12(d,J=7.9Hz,1H),2.42(s,3H);

[0174] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.65,157.35,147.11,137.12,136.05,134.7 2,127.56,127.04,125.81,125.63,121.21,120.23,119.64,118.52,21.73;

[0175] MS(EI,70eV)m / z 266,249,237,205,180.

[0176] Example 15

[0177] The 12H-benzo[4,5]thiazo[2,3-b]quinazolin-12-one compound obtained in this example has the following structure:

[0178]

[0179] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 2-iodo-1-thioisocyanate-4-methoxybenzene, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 85% and a purity of 99.9%.

[0180] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0181] 1 H NMR (400MHz, CDCl3, ppm) δ8.89(d,J=9.2Hz,1H),8.40(d,J=6.9Hz,1H),7.79-7.74(m,1H),7.64(d ,J=8.7Hz,1H),7.49-7.43(m,1H),7.09(d,J=2.6Hz,1H),6.98(dd,J=9.2,2.6Hz,1H),3.85(s,3H);

[0182] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.38,158.25,156.89,147.19,134.63,129.8 1,126.98,125.90,125.74,125.15,120.12,118.62,112.90,106.72,55.76;

[0183] MS(EI,70eV)m / z 282,267,239,211,167.

[0184] Example 16

[0185] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0186]

[0187] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 1-iodo-2-thioisocyanate-4-methoxybenzene, 0.02 mmol of copper trifluoromethanesulfonate as catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 85% and a purity of 99.9%.

[0188] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0189] 1 H NMR (400MHz, CDCl3, ppm) δ8.68(d,J=2.6Hz,1H),8.39(d,J=8.0Hz,1H),7.79(d,J=7.1Hz ,1H),7.64(d,J=8.2Hz,1H),7.48-7.43(m,2H),7.00(dd,J=8.7,2.6Hz,1H),3.91(s,3H);

[0190] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.96,158.95,157.98,147.22,137.01,134.9 0,127.06,125.91,125.73,122.03,118.44,114.69,114.39,104.57,55.84;

[0191] MS(EI,70eV)m / z 282,267,253,239,211.

[0192] Example 17

[0193] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0194]

[0195] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 1-chloro-2-iodide-3-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 88% and a purity of 99.9%.

[0196] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0197] 1 H NMR (400MHz, CDCl3, ppm) δ8.88(d,J=7.4Hz,1H),8.39(d,J=8.0Hz,1H),7.79(t,J=7.7Hz,1H),7.66(d,J=7.9Hz,1H),7.50-7.40(m,3H);

[0198] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.56,156.10,147.00,136.80,135.09,127.96,127.21,127.17,126.41,126.13,126.12,124.12,118.52,117.17;

[0199] MS(EI,70eV)m / z 286,258,232,223,207.

[0200] Example 18

[0201] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0202]

[0203] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 4-chloro-1-iodo-2-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 89% and a purity of 99.9%.

[0204] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0205] 1 H NMR (400MHz, CDCl3, ppm) δ9.06 (s, 1H), 8.40 (d, J = 6.8Hz, 1H), 7.82-7.77 (m, 1H), 7.65 (d, J = 8.2Hz, 1H), 7.53-7.47 (m, 2H), 7.42 (s, 1H);

[0206] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.52,156.63,147.03,136.62,135.13,132.91,127.19,126.97,126.11,126.01,122.37,122.06,119.49,118.39;

[0207] MS(EI,70eV)m / z 286,258,251,232,223.

[0208] Example 19

[0209] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0210]

[0211] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 4-bromo-2-iodo-1-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. The purified target product was obtained after column chromatography with a yield of 89% and a purity of 99.9%.

[0212] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0213] 1 H NMR(400MHz, CDCl3, ppm) δ8.89(d,J=8.9Hz,1H),8.42(d,J=9.3Hz,1H),7.84-7 .74(m,2H),7.67(d,J=8.1Hz,1H),7.61(d,J=8.9Hz,1H),7.51(t,J=8.0Hz,1H);

[0214] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.62,156.17,147.19,135.12,130.01,127.18,126.18,126.10,125.74,124.49,120.36,119.90,118.57;

[0215] MS(EI,70eV)m / z 331,304,251,223,196.

[0216] Example 20

[0217] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0218]

[0219] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 4-bromo-1-iodo-2-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 77% and a purity of 99.9%.

[0220] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0221] 1 H NMR (400MHz, CDCl3, ppm) δ9.20 (s, 1H), 8.40 (d, J = 8.0Hz, 1H), 7.80 (t, J = 7.7Hz, 1H), 7.65 (d, J = 8.2Hz, 1H), 7.56 (d, J = 8.4Hz, 1H), 7.51-7.45 (m, 2H);

[0222] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ160.56,156.45,147.06,136.82,135.16,129.82,127.21,126.15,126.04,122.72,122.70,122.26,120.38,118.42;

[0223] MS(EI,70eV)m / z 331,304,251,223,196.

[0224] Example 21

[0225] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0226]

[0227] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 4-fluoro-2-iodo-1-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 77% and a purity of 99.9%.

[0228] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0229] 1 H NMR (400MHz, CDCl3, ppm) δ8.98 (dd, J=9.2, 4.8Hz, 1H), 8.39 (d, J=9.4Hz, 1H), 7.81-7.74 (m, 1H), 7. 64(d,J=8.0Hz,1H),7.48(t,J=7.6Hz,1H),7.32(dd,J=7.6,2.6Hz,1H),7.17(td,J=8.9,2.7Hz,1H);

[0230] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ161.92,160.51,159.44,156.52,147.13,134.98,132.40,127.09,126 .05(d,J=5.0Hz),125.5(d,J=10.0Hz),120.56(d,J=9.0Hz),118.56,114.12,109.10(d,J=28.0Hz);

[0231] MS(EI,70eV)m / z 270,242,216,210,197.

[0232] Example 22

[0233] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0234]

[0235] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of 4-fluoro-1-iodo-2-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 89% and a purity of 99.9%.

[0236] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0237] 1 H NMR (400MHz, CDCl3, ppm) δ8.74(d,J=12.6Hz,1H),8.34(d,J=7.3Hz,1H),7.75(t,J=7.6Hz,1H) ,7.59(d,J=8.2Hz,1H),7.50(dd,J=8.7,5.1Hz,1H),7.44(t,J=7.5Hz,1H),7.17-7.11(m,1H);

[0238] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ162.60,160.49,160.16,157.22,147.03,136.61(d,J=13.0Hz),135.06,127.1 4,125.97,122.38(d,J=9.0Hz),118.74(d,J=3.0Hz),118.29,114.29(d,J=23.0Hz),107.60(d,J=31.0Hz);

[0239] MS(EI,70eV)m / z 270,242,216,210,197.

[0240] Example 23

[0241] The 12H-benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds obtained in this example have the following structures:

[0242]

[0243] 0.1 mmol of 2-aminobenzamide, 0.1 mmol of phenyl 5-chloro-1-fluoro-3-iodo-2-thioisocyanate, 0.02 mmol of copper trifluoromethanesulfonate as a catalyst, and 1 mL of DMSO were added to a reaction tube. The mixture was stirred at 100 °C for 1 h. After the reaction was completed, the resulting reaction system was purified by column chromatography. The eluent used for column chromatography was a mixed solvent of petroleum ether and ethyl acetate, with a volume ratio of petroleum ether to ethyl acetate of 5:1. After column chromatography purification, the purified target product was obtained with a yield of 60% and a purity of 99.9%.

[0244] The structure of the obtained product was characterized, and the structural characterization data are as follows:

[0245] 1 H NMR (400MHz, CDCl3, ppm) δ8.38(d,J=8.0Hz,1H),7.82-7.77(m,1H),7.62(d,J=8.7Hz,1H),7.49(t,J=7.6Hz,1H),7.39(s,1H),7.29-7.26(m,1H);

[0246] 13 C{ 1 H}NMR (100MHz, CDCl3, ppm) δ 158.46, 155.61, 151.76, 149.12, 146.87, 135.14, 133.34 (d, J = 10.0Hz), 128. 25(d,J=4.0Hz),127.63,126.37,125.70,118.91(d,J=3.0Hz), 117.75(d,J=4.0Hz), 116.77(d,J=27.0Hz);

[0247] MS(EI,70eV)m / z 304,276,250,241,232.

[0248] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A type of 12 H A method for preparing benzo[4,5]thiazo[2,3-b]quinazolin 12-one compounds, characterized in that, Includes the following steps: A mixture of 2-aminobenzamide compounds, 2-iodophenyl isothiocyanate compounds, a catalyst, and a polar organic solvent was subjected to a coupling addition reaction to yield 12 H -Benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds; The 2-aminobenzamide compounds have the structure shown in Formula I: Formula I; The 2-iodophenyl isothiocyanate compound has the structure shown in Formula II: Formula II; The 12 H -Benzo[4,5]thiazo[2,3-b]quinazoline 12-one compounds have the structure shown in Formula III: Formula III; In Equations I and III Selected from , or ； The number of R1 groups is 1 to 4; the R1 groups are selected from one or more of hydrogen, alkyl, alkoxy and halogen groups. The number of R2 groups is 1 to 4; the R2 groups are selected from one or more of hydrogen, alkyl, alkoxy and halogen groups; The catalyst is copper trifluoromethanesulfonate.

2. The preparation method according to claim 1, characterized in that, The 2-aminobenzamide compounds are selected from one or more of 2-aminobenzamide, 2-amino-3-methylbenzamide, 2-amino-4-methylbenzamide, 2-amino-5-methylbenzamide, 2-amino-5-methoxybenzamide, 2-amino-4-fluorobenzamide, 2-amino-3-bromobenzamide, 2-amino-5-bromobenzamide, 2-amino-4-chlorobenzamide, 2-amino-5-chlorobenzamide, 3-aminothiophene-2-carboxamide, and 3-amino-2-naphthylcarboxamide; The 2-iodophenyl isothiocyanate compounds are selected from one or more of the following: 2-iodophenyl isothiocyanate, 2-iodo-1-thioisocyanate-4-methylbenzene, 1-iodo-2-thioisocyanate-4-methylbenzene, 2-iodo-1-thioisocyanate-4-methoxybenzene, 1-iodo-2-thioisocyanate-4-methoxybenzene, 1-chloro-2-iodo-3-thioisocyanate, 4-chloro-1-iodo-2-thioisocyanate, 4-bromo-2-iodo-1-thioisocyanate, 4-bromo-1-iodo-2-thioisocyanate, 4-fluoro-2-iodo-1-thioisocyanate, 4-fluoro-1-iodo-2-thioisocyanate, and 5-chloro-1-fluoro-3-iodo-2-thioisocyanate.

3. The preparation method according to claim 1 or 2, characterized in that, The molar ratio of the 2-aminobenzamide compound and the 2-iodoisothiocyanate phenyl ester compound is 1:

1.

4. The preparation method according to claim 1, characterized in that, The molar ratio of the 2-aminobenzamide compound to the catalyst is 1:0.2~0.

5.

5. The preparation method according to claim 1, characterized in that, The polar organic solvent is selected from dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, or toluene.

6. The preparation method according to claim 1 or 5, characterized in that, The ratio of the polar organic solvent to the 2-aminobenzamide compound is 1 L: 0.1~0.2 mol.

7. The preparation method according to claim 1, characterized in that, The coupling addition reaction is carried out at a temperature of 80~130℃ for 1~12h.

Images