Method for electrocatalytic synthesis of quinazolinone derivative

Abstract

The invention belongs to the technical field of synthesis of quinazolinone derivatives. The invention discloses a method for electrocatalytic synthesis of a quinazoline-4 (3H)-ketone derivative, which comprises the following steps: adding an anthranilamide derivative, an isothiocyanate derivative, an electrolyte, an additive, methanol and acetonitrile into an electrolytic tank, and introducing a direct-current constant current between an anode and a cathode for reaction. The reaction conditions are mild, and the harsh temperature requirement in the reaction is solved. The method does not need expensive metal catalyst lanthanum, and is economical, practical, green and environment-friendly.

Description

Technical Field

[0001] The invention belongs to the technical field of synthesis of quinazolinone derivatives. Background Art

[0002] Quinazolin-4(3H)-one derivatives are unique compounds whose core skeletons fuse the quinazoline ring with the keto carbonyl group at the 4th position, forming a molecular structure with polycyclic characteristics. This type of compound has shown important potential in many fields due to its unique physicochemical properties and wide biological activities. By introducing different substituents to modify its structure, its electronic properties and biological activities can be further regulated. Quinazolin-4(3H)-one derivatives have shown significant potential application value in drug development, material science and other application fields. Quinazolin-4(3H)-one derivatives have a variety of biological activities such as anti-tumor, anti-inflammatory, and antibacterial, especially in the development of anticancer drugs. Among them, Fenquizone, a quinazolin-4(3H)-one derivative, can be used to detect specific enzyme activities. Idelalisib is an inhibitor targeting PI3Kδ, which is widely used in the treatment of chronic lymphocytic leukemia and small lymphocytic lymphoma, showing significant efficacy, but may also cause some adverse reactions. These compounds are of great significance in the field of medicine.

[0003]

[0004] Ming-Wu Ding's group developed a palladium-catalyzed method for the synthesis of quinazolin-4(3H)-ones.

[0005]

[0006] Sabuj Kundu's research group developed a method to synthesize quinazolin-4(3H)-one under 35W blue light.

[0007]

[0008] In the process of synthesizing such compounds, conventional synthesis methods require the use of expensive transition metal catalysts, photocatalysts, strong acids, etc., which makes the reaction process dangerous and costly. Summary of the invention

[0009] The method adopts electrocatalysis with o-aminobenzamide and phenyl isothiocyanate as reaction substrates, acetonitrile and methanol and other cheap and less toxic reagents as solvents, and replaces the oxidant and reductant in the conventional reaction by passing electric current, and adopts a mild and green electrocatalytic method to synthesize quinazoline-4(3H)-one compounds. BRIEF DESCRIPTION OF THE DRAWINGS

[0010] Figure 1 This is the hydrogen spectrum of compound 3aa of Example 1.

[0011] Figure 2 This is the carbon spectrum of compound 3aa of Example 1.

[0012] Figure 3 This is the hydrogen spectrum of compound 3ba from Example 2.

[0013] Figure 4 This is the carbon spectrum of compound 3ba from Example 2.

[0014] Figure 5 This is the hydrogen spectrum of compound 3ca of Example 3.

[0015] Figure 6 This is the carbon spectrum of compound 3ca of Example 3.

[0016] Figure 7 This is the hydrogen spectrum of compound 3da of Example 4.

[0017] Figure 8 This is the carbon spectrum of compound 3da of Example 4.

[0018] Fig. 9 This is the hydrogen spectrum of Example 5 compound 3ea.

[0019] Fig.10 This is the carbon spectrum of compound 3ea of ​​Example 5.

[0020] Fig.11 This is the hydrogen spectrum of compound 3fa of Example 6.

[0021] Fig.12 This is the carbon spectrum of compound 3fa of Example 6.

[0022] Fig.13 This is the hydrogen spectrum of Example 7 compound 3ab.

[0023] Fig.14 This is the carbon spectrum of compound 3ab of Example 7.

[0024] Fig.15 This is the hydrogen spectrum of Example 8 compound 3ac.

[0025] Fig.16 This is the carbon spectrum of compound 3ac of Example 8.

[0026] Fig.17 This is the hydrogen spectrum of compound 3ad of Example 9.

[0027] Fig.18 This is the carbon spectrum of compound 3ad of Example 9.

[0028] Fig.19 This is the hydrogen spectrum of compound 3ga of Example 10.

[0029] Fig. 20 This is the carbon spectrum of compound 3ga of Example 10.

[0030] Fig.21 This is the hydrogen spectrum of compound 3ha of Example 11.

[0031] Fig. 22 This is the carbon spectrum of compound 3ha from Example 11.

[0032] Fig.23 This is the hydrogen spectrum of compound 3ae of Example 12.

[0033] Fig.24 This is the carbon spectrum of compound 3ae of Example 12.

[0034] Fig.25 This is the hydrogen spectrum of Example 13 compound 3af.

[0035] Fig.26 This is the carbon spectrum of compound 3af of Example 13. DETAILED DESCRIPTION

[0036] Example

[0037] The invention discloses a method for electrocatalytically synthesizing quinazoline-4(3H)-one derivatives. The reaction is carried out under power-on conditions, has good substrate practicality, high yield, and various substituted quinazoline-4(3H)-ones are obtained with good yields.

[0038] The raw materials include o-aminobenzamide derivatives and isothiocyanate derivatives, the electrolyte is tetrabutylammonium iodide, the additive is o-phenanthroline, and the solvents are methanol and acetonitrile.

[0039] The experimental equipment includes carbon electrodes (Φ=6 mm, purchased), foam nickel electrodes (1.0 cm×1.0 cm×0.3 cm, purchased), a 20 ml electrolytic cell, a magnet, and a DC regulated power supply.

[0040] The compound with the general formula 1, the compound with the general formula 2, the electrolyte, the additive, methanol, acetonitrile, and the magnet were sequentially added to the electrolytic cell, a DC constant current of 7 mA was passed between the anode and cathode electrodes, the reaction was carried out at 25° C. for 10 h, and the reaction progress was monitored by thin layer chromatography until the reaction was complete; finally, the compound with the general formula 3 was obtained by separation and purification by silica gel column chromatography (petroleum ether: ethyl acetate). The reaction equation is as follows

[0041]

[0042] The preparation method of this example comprises the following steps: 1a (0.2 mmol), tetrabutylammonium iodide (0.4 mmol), o-phenanthroline (0.4 mmol), methanol (2.5 mL), acetonitrile (2.5 mL), a magnet, and 2a (0.4 mmol) are sequentially added into an electrolytic cell, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, respectively; a DC constant current of 7 mA is passed between the anode and the cathode of the electrode; the reaction is carried out at 25° C. for 10 h, and the reaction progress is monitored by thin layer chromatography until the reaction is complete; and finally, the compound 3aa is separated and purified by silica gel column chromatography to obtain a yield of 82%.

[0043] The reaction equation is as follows:

[0044]

[0045] The spectrum data of compound 3aa are as follows:

[0046] 1 H NMR (400MHz, CDCl3, ppm): δ8.17 (dd, J=8.0, 1.6Hz, 1H), 7.68-7.57 (m, 4H), 7.52 (t, J= 8.4Hz, 3H), 7.42-7.40 (m, 2H), 7.33-7.23 (m, 3H), 7.08 (t, J=7.4Hz, 1H), 5.96 (s, 1H).

[0047] 13 C NMR (100MHz, CDCl3, ppm): δ162.6, 148.6, 146.4, 137.9, 134.8, 134.6, 130.9, 130.4, 129.1, 129.0, 127.3, 125.7, 124.1, 123.8, 120.9, 118.5.

[0048] Example 2:

[0049] The preparation method of this embodiment comprises the following steps: 1b (0.2mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnetron, 2a (0.4mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7mA is passed between the anode and the cathode, the reaction is carried out at 25°C for 10h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ba is separated and purified by silica gel column chromatography to obtain a yield of 79%. The reaction equation is as follows:

[0050]

[0051] The spectrum data of compound 3ba are as follows:

[0052] 1 H NMR (400MHz, CDCl3, ppm): δ7.98 (s, 1H), 7.67-7.58 (m, 3H), 7.52-7.40 (m, 6H), 7.31 (t, J=7.6Hz, 2H), 7.09 (t, J=7.6Hz, 1H), 5.96 (s, 1H), 2.44 (s, 3H).

[0053] 13 C NMR (100MHz, CDCl3, ppm): δ162.6, 146.4, 145.9, 138.1, 136.3, 134.8, 133.6, 130.9, 130.3, 129.2, 129.0, 126.7, 125.5, 124.0, 120.8, 118.2, 21.1.

[0054] Example 3:

[0055] The preparation method of this embodiment comprises the following steps: 1c (0.2mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnetron, 2a (0.4mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7mA is passed between the anode and the cathode, the reaction is carried out at 25°C for 10h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ca is separated and purified by silica gel column chromatography to obtain a yield of 74%. The reaction equation is as follows:

[0056]

[0057] The spectrum data of compound 3ca are as follows:

[0058] 1 H NMR (400MHz, CDCl3, ppm): δ7.81 (dd, J=8.4, 3.2Hz, 1H), 7.68-7.59 (m, 3H), 7.53-7.47 (m, 3H), 7.42-7.36 (m, 3H), 7.31 (t, J=8.0Hz, 2H), 7.16 (t, J=7.6Hz, 1H), 5.96 (s, 1H).

[0059] 13C NMR (100MHz, CDCl3, ppm): δ161.9 (d, J=3.3Hz, 1C), 160.3, 157.9, 146.1, 145.2, 137.8, 134.5, 131.0, 130.5, 129.1 (d, J=3 .3Hz, 1C), 127.8 (d, J=7.7Hz, 1C), 124.3, 123.4 (d, J=23.9Hz, 1C), 121.0, 119.2 (d, J=8.5Hz, 1C), 112.0 (d, J=23.4Hz, 1C).

[0060] Example 4:

[0061] The preparation method of this embodiment comprises the following steps: 1d (0.2mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnetron, 2a (0.4mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7mA is passed between the anode and the cathode, the reaction is carried out at 25°C for 10h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3da is separated and purified by silica gel column chromatography to obtain a yield of 45%. The reaction equation is as follows:

[0062]

[0063] The spectral data of compound 3da are as follows:

[0064] 1 H NMR (400MHz, DMSO, ppm): δ9.39 (s, 1H), 8.74 (s, 1H), 8.09 (d, J=8.4Hz, 1H), 7.75 (dd, J=7.6, 1.6Hz, 1H), 7. 66-7.62 (m, 1H), 7.49 (dd, J=8.4, 1.2Hz, 2H), 7.33-7.29 (m, 2H), 7.20-7.16 (m, 1H), 7.01 (t, J=7.4Hz, 1H).

[0065] 13 C NMR (100MHz, DMSO, ppm): δ 152.0, 142.0, 139.2, 134.0, 133.1, 128.9, 123.0, 122.4, 121.3, 118.4, 117.0, 102.0.

[0066] Example 5:

[0067] The preparation method of this embodiment comprises the following steps: 1e (0.2mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnetron, 2a (0.4mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7mA is passed between the anode and the cathode, the reaction is carried out at 25°C for 10h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ea is separated and purified by silica gel column chromatography to obtain a yield of 61%. The reaction equation is as follows:

[0068]

[0069] The spectral data of compound 3ea are as follows:

[0070] 1 H NMR (400MHz, CDCl3, ppm): δ8.17 (dd, J=8.0, 1.6Hz, 1H), 7.68-7.63 (m, 1H), 7.54-7.52 (m , 3H), 7.34-7.30(m, 4H), 7.27-7.23(m, 1H), 7.15-7.07(m, 3H), 6.10(s, 1H), 3.90(s, 3H).

[0071] 13 C NMR (100MHz, CDCl3, ppm): δ162.9, 160.8, 148.6, 146.8, 138.0, 134.8, 130.3, 129.0, 127.3, 126.7, 125.7, 124.0, 123.7, 120.8, 118.6, 116.2, 55.8.

[0072] Example 6:

[0073] The preparation method of this embodiment comprises the following steps: 1f (0.2 mmol), tetrabutylammonium iodide (0.4 mmol), o-phenanthroline (0.4 mmol), methanol (2.5 mL), acetonitrile (2.5 mL), magnetron, 2a (0.4 mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7 mA is passed between the anode and the cathode, the reaction is carried out at 25° C. for 10 h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3fa is separated and purified by silica gel column chromatography to obtain a yield of 64%. The reaction equation is as follows:

[0074]

[0075] The spectrum data of compound 3fa are as follows:

[0076] 1 H NMR (400MHz, CDCl3, ppm): δ8.16 (dd, J=8.0, 1.6Hz, 1H), 7.68-7.64 (m, 1H), 7.53 (d, J=8.8Hz, 3H), 7.42-7.39(m, 2H), 7.36-7.30(m, 4H), 7.28-7.24(m, 1H), 7.12-7.08(m, 1H), 5.90(s, 1H).

[0077] 13 C NMR (100MHz, CDCl3, ppm): δ164.7, 162.7, 162.2, 148.5, 146.3, 137.8, 135.0, 131.2 (d, J=8.9Hz, 1C), 130 .4(d, J=3.4Hz, 1C), 129.1, 127.3, 125.8, 124.1 (d, J=36.1Hz, 1C), 121.0, 118.4, 118.1 (d, J=23.0Hz, 1C).

[0078] Example 7:

[0079] The preparation method of this embodiment comprises the following steps: 1a (0.2 mmol), tetrabutylammonium iodide (0.4 mmol), o-phenanthroline (0.4 mmol), methanol (2.5 mL), acetonitrile (2.5 mL), magnetron, 2b (0.4 mmol) are sequentially added to an electrolytic cell, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7 mA is passed between the anode and the cathode, the reaction is carried out at 25° C. for 10 h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ab is separated and purified by silica gel column chromatography to obtain a yield of 67%. The reaction equation is as follows:

[0080]

[0081] The spectral data of compound 3ab are as follows:

[0082] 1 H NMR (400MHz, CDCl3, ppm): δ8.18 (dd, J=8.0, 1.6Hz, 1H), 7.71-7.61 (m, 6H), 7.57-7.54 (m, 3H), 7.42-7.40 (m, 2H), 7.30 (t, J=7.4Hz, 1H), 6.13 (s, 1H).

[0083] 13C NMR (100MHz, CDCl3, ppm): δ162.4, 148.1, 145.7, 141.1, 135.0, 134.3, 131.1, 130.6, 129.1, 127.4, 12 6.2 (q, J=3.7Hz, 1C), 125.7 (q, J=32.7Hz, 1C), 125.6 (q, J=270.0Hz, 1C), 124.4, 122.9, 120.1, 118.8.

[0084] Example 8:

[0085] The preparation method of this embodiment comprises the following steps: 1a (0.2 mmol), tetrabutylammonium iodide (0.4 mmol), o-phenanthroline (0.4 mmol), methanol (2.5 mL), acetonitrile (2.5 mL), magnetron, 2c (0.4 mmol) are sequentially added to an electrolytic cell, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7 mA is passed between the anode and the cathode, the reaction is carried out at 25° C. for 10 h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ac is separated and purified by silica gel column chromatography to obtain a yield of 79%. The reaction equation is as follows:

[0086]

[0087] The spectral data of compound 3ac are as follows:

[0088] 1 H NMR (400MHz, CDCl3, ppm): δ8.17 (dd, J=8.0, 1.6Hz, 1H), 7.67-7.58 (m, 4H), 7.51 (d, J=8.4H z, 1H), 7.42-7.39 (m, 4H), 7.34-7.32 (m, 2H), 7.26-7.22 (m, 1H), 5.89 (s, 1H), 1.30 (s, 9H).

[0089] 13 C NMR (100MHz, CDCl3, ppm): δ162.6, 148.7, 147.2, 146.6, 135.2, 134.8, 134.7 , 130.9, 130.3, 129.1, 127.3, 125.8, 125.7, 123.6, 120.8, 118.5, 34.4, 31.5.

[0090] Example 9:

[0091] The preparation method of this embodiment comprises the following steps: 1a (0.2 mmol), tetrabutylammonium iodide (0.4 mmol), o-phenanthroline (0.4 mmol), methanol (2.5 mL), acetonitrile (2.5 mL), magnetron, 2d (0.4 mmol) are sequentially added to an electrolytic cell, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7 mA is passed between the anode and the cathode, the reaction is carried out at 25° C. for 10 h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ad is separated and purified by silica gel column chromatography to obtain a yield of 53%. The reaction equation is as follows:

[0092]

[0093] The spectral data of compound 3ad are as follows:

[0094] 1 H NMR (400MHz, CDCl3, ppm): δ8.14 (dd, J=8.0, 1.6Hz, 1H), 7.64-7.60 (m, 1H), 7.58-7.54 (m, 2H), 7.51-7.43 (m, 2 H), 7.32-7.28 (m, 4H), 7.25-7.23 (m, 3H), 7.18 (t, J=7.4Hz, 1H), 4.66 (d, J=5.6Hz, 2H), 4.40 (t, J=5.4Hz, 1H).

[0095] 13 C NMR (100MHz, CDCl3, ppm): δ162.8, 149.5, 149.5, 138.5, 134.8, 130.7, 130.0, 128.9, 128.8, 127.6, 127.5, 127.4, 125.2, 122.9, 117.9, 45.6.

[0096] Example 10:

[0097] The preparation method of this embodiment comprises the following steps: 1g (0.2mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnet, 2a (0.4mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7mA is passed between the anode and the cathode, the reaction is carried out at 25°C for 10h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ga is separated and purified by silica gel column chromatography to obtain a yield of 70%. The reaction equation is as follows:

[0098]

[0099] The spectrum data of compound 3ga are as follows:

[0100] 1 H NMR (400MHz, CDCl3, ppm): δ8.11 (d, J=2.4Hz, 1 H), 7.67-7.64 (m, 2H), 7.62-7.56 (m, 2H), 7.48-7.45 (m, 3H), 7.41-7.39 (m, 2H), 7.31 (t, J=7.8Hz, 2H), 7.10 (t, J=7.4Hz, 1H), 6.01 (s, 1H).

[0101] 13 C NMR (100MHz, CDCl3, ppm): δ161.6, 147.1, 146.7, 137.6, 135.2, 134.3, 131.1, 130.6, 129.2, 129.1, 127.3, 126.5, 124.5, 121.2, 119.5.

[0102] Example 11:

[0103] The preparation method of this embodiment comprises the following steps: 1h (0.2mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnetron, 2a (0.4mmol) are added to the electrolytic cell in sequence, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7mA is passed between the anode and the cathode, the reaction is carried out at 25°C for 10h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ha is separated and purified by silica gel column chromatography to obtain a yield of 76%. The reaction equation is as follows:

[0104]

[0105] The spectrum data of compound 3ha are as follows:

[0106] 1 H NMR (400MHz, DMSO, ppm): δ8.82 (d, J=6.4Hz, 2H), 7.98 (d, J=7.6Hz, 1H), 7.80 (s, 1H), 7.67 (t, J=7.4Hz, 1H), 7. 61 (d, J=6.0Hz, 2H), 7.50 (d, J=6.0Hz, 2H), 7.31 (t, J=8.2Hz, 3H), 7.25 (t, J=7.4Hz, 1H), 7.09 (t, J=7.4Hz, 1H).

[0107] 13C NMR (100MHz, DMSO, ppm): δ 161.4, 151.5, 148.7, 147.4, 142.9, 138.8, 134.8, 128.1, 126.5, 125.1, 124.9, 123.9, 123.7, 123.1, 117.7.

[0108] Example 12:

[0109] The preparation method of this embodiment comprises the following steps: 1a (0.2 mmol), tetrabutylammonium iodide (0.4 mmol), o-phenanthroline (0.4 mmol), methanol (2.5 mL), acetonitrile (2.5 mL), magnetron, 2e (0.4 mmol) are sequentially added to an electrolytic cell, a carbon rod is used as an anode, and a nickel foam sheet is used as a cathode, a DC constant current of 7 mA is passed between the anode and the cathode, the reaction is carried out at 25° C. for 10 h, the reaction progress is monitored by thin layer chromatography until the reaction is complete, and finally, the compound 3ae is separated and purified by silica gel column chromatography to obtain a yield of 81%. The reaction equation is as follows:

[0110]

[0111] The spectrum data of compound 3ae are as follows:

[0112] 1 H NMR (400MHz, CDCl3, ppm): δ8.16 (d, J=7.6Hz, 1H), 7.66-7.56 (m, 4H), 7.50 (d, J=8.4Hz, 1H ), 7.41-7.36 (m, 4H), 7.25-7.21 (m, 1H), 7.11 (d, J=8.0Hz, 1H), 5.87 (s, 1H), 2.31 (s, 3H).

[0113] 13 C NMR (100MHz, CDCl3, ppm): 6162.7, 148.8, 146.7, 135.3, 134.8, 134.7, 133.9, 130.9, 130.3, 129.5, 129.1, 127.3, 125.7, 123.6, 121.3, 118.4, 21.0.

[0114] Example 13:

[0115] The preparation method of this embodiment comprises the following steps: adding 1a (0.2

[0116] mmol), tetrabutylammonium iodide (0.4mmol), o-phenanthroline (0.4mmol), methanol (2.5mL), acetonitrile (2.5mL), magnetron, 2f (0.4mmol), respectively, using carbon rod as anode and nickel foam as cathode, passing a DC constant current of 7mA between the anode and cathode, reacting at 25°C for 10h, monitoring the reaction progress with thin layer chromatography until the reaction is complete, and finally separating and purifying by silica gel column chromatography to obtain compound 3af with a yield of 71%. The reaction equation is as follows:

[0117]

[0118] The spectrum data of compound 3af are as follows:

[0119] 1 H NMR (400MHz, CDCl3, ppm): δ8.16 (dd, J=8.0, 1.6Hz, 1H), 7.68-7.57 (m, 4H), 7.52-7.45 (m, 3H), 7.41-7.38 (m, 2H), 7.28-7.24 (m, 3H), 5.94 (s, 1H).

[0120] 13 C NMR (100MHz, CDCl3, ppm): δ162.5, 148.3, 146.2, 136.5, 134.9, 134.5, 131.0, 130.5, 129.1, 129.0, 128.9, 127.3, 125.7, 124.0, 122.2, 118.6.

[0121] The reaction conditions of the present invention are mild, which solves the harsh temperature requirement in the reaction and does not require expensive metal catalyst lanthanum, which is economical, affordable and environmentally friendly.

Claims

1. A method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives, characterized in that: include: An o-aminobenzamide derivative, an isothiocyanate derivative, an electrolyte, an additive, methanol and acetonitrile are added into an electrolytic cell, and a direct current constant current is passed between the anode and cathode electrodes for reaction.

2. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The anthranilamide derivative has the following structural formula: Among them, R 1 is hydrogen, methyl, fluorine or chlorine; R 2 is phenyl, hydrogen, 4-methoxyphenyl, 4-fluorophenyl, 4-pyridyl or 4-chlorophenyl.

3. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The isothiocyanate derivative has the following structural formula: R 3 -NCS; among them, R 3 The phenyl radicals are phenyl, 4-trifluoromethylphenyl, 4-tert-butylphenyl, benzyl, 4-tolyl and 4-chlorophenyl.

4. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The electrolyte is tetrabutylammonium iodide.

5. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The additive is o-phenanthroline.

6. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The amount ratio of the o-aminobenzamide derivative, the isothiocyanate derivative, the electrolyte and the additive is 1:2:2:

2.

7. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The volume ratio of the methanol to acetonitrile is 1:

1.

8. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The anode is a carbon rod, and the cathode is a nickel foam sheet.

9. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The DC constant current is 7 mA.

10. The method for electrocatalytic synthesis of quinazolin-4(3H)-one derivatives according to claim 1, characterized in that: The reaction temperature is 25° C., and the reaction time is 10 h.

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