Synthesis method of 1, 2, 3-triazole quinoxalinone derivative

A technology of triazole quinoxalinone and synthesis method, which is applied in the direction of organic chemistry and the like, can solve the problems of many steps, narrow range of substrate universality, low yield and the like, and achieves the effect of strong biological activity

Active Publication Date: 2022-03-18
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the synthesis of these structures, and the reported traditio

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  • Synthesis method of 1, 2, 3-triazole quinoxalinone derivative
  • Synthesis method of 1, 2, 3-triazole quinoxalinone derivative
  • Synthesis method of 1, 2, 3-triazole quinoxalinone derivative

Examples

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Example Embodiment

[0021] Example 1

[0022] Under blue light irradiation, 1-methyl quinoxalin (0.5 mmol), diazon trivalent iodine reagent 1 (0.75 mmol), three (2,2'-bispyridine) dichloride (5% mmol) and 1,1 dichloroethane (2 mL) was added to 15 ml of tubes, and the reaction was reacted at room temperature for 10 hours, and the silica gel column chromatography was separated to obtain a yield of the target compound 3a of 66%. 1 H NMR (300MHz, CDCL 3 Δ8.61 (DD, J = 8.7, 1.7 Hz, 1H), 7.68-7.62 (M, 1H), 7.49-7.44 (M, 2H), 4.56 (Q, J = 7.1 Hz, 2H), 3.77 (S , 3H), 1.49 (T, J = 7.1 Hz, 3H).

Example Embodiment

[0023] Example 2

[0024] Under blue light irradiation, 7-fluoro-1-methyl quinoxalinone (0.5 mmol), diazon trivalent iodine reagent 1 (0.75 mmol), three (2,2'-bispyridine) dichloride (5) % Mmol) and 1,1-dichloroethane (2 mL) were added to 15 ml of tubes, and the reaction was reacted at room temperature for 12 hours, and the silica gel column chromatography was separated to obtain a yield of the target compound 3B of 75%. 1 H NMR (500MHz, CDCL 3 Δ8.33 (DD, J = 7.9, 2.8 Hz, 1H), 7.49-7.46 (M, 1H), 7.42-7.40 (M, 1H), 4.57 (Q, J = 7.1 Hz, 2H), 3.78 (S 3h).

Example Embodiment

[0025] Example 3

[0026] Under blue light irradiation, 7-chloro-1-methyl quinolinone (0.5 mmol), diazon trivalent iodine reagent 1 (0.75 mmol), three (2,2'-bispyridine) dichloride (5) % Mmol) and 1,1-dichloroethane (2 mL) were added to 15 ml of test tubes, and the reaction was separated at room temperature, and the silica gel column chromatography was separated, and the yield of the target compound 3c was 80%. 1 H NMR (300MHz, CDCL 3 Δ8.53 (D, J = 2.0 Hz, 1H), 7.53 (DD, J = 8.9, 2.2 Hz, 1H), 7.34 (D, J = 9.0Hz, 1H), 4.48 (Q, J = 7.1 Hz, 2H), 3.67 (S, 3H), 1.41 (t, j = 7.1 Hz, 3H).

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Abstract

The invention belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of a 1, 2, 3-triazole quinoxalinone derivative. Under ruthenium catalysis, a quinoxaline ketone derivative and a diazonium trivalent iodine reagent are used as raw materials, under blue light irradiation, stirring is performed in a solvent, and a reaction is performed at room temperature to obtain the 1, 2, 3-triazole quinoxaline ketone derivative. By using the method provided by the invention, the 1, 2, 3-triazole quinoxalinone derivative can be obtained by reacting for 10-15 hours at room temperature, and the yield is 66-82%. According to the reaction, the 1, 2, 3-triazole quinoxalinone derivative is simply, conveniently and rapidly synthesized by adopting simple and easily available raw materials under the conditions of ruthenium catalysis and blue light irradiation, and a novel simple, efficient and mild synthesis method is provided for synthesizing the 1, 2, 3-triazole quinoxalinone derivative.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicine, in particular to a synthesis method of 1,2,3-triazolequinoxalinone derivatives. Background technique [0002] Heterocyclic compounds are the largest class of organic compounds, which are commonly found in drug molecules. Heteropolycyclic compounds, especially 1,2,3-triazolequinoxalinone derivatives and their similar tricyclic systems, have shown strong biological activities, such as G-protein coupled hydrochloric acid receptor 109A antagonists, diazepam receptor inhibitors, etc. [(a) Sharma, S.; Sharma, P.K.; Kumar, N.; Dudhe, R. Pharma. Chemica., 2010, 2, 253. (b) Khalilullah, H.; Ahsan, M.J.; Hedaitullah, M.; Khan, S.; Ahmed, B. Mini-Rev. Med. Chem., 2012, 12, 789]. However, there are few reports on the synthesis of these structures, and the reported traditional methods have limitations such as many steps, narrow substrate universality, and low yields. [0003] At pre...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 李剑赵文艳朱娅南邓长江董春萍陈俊名马晓明
Owner CHANGZHOU UNIV
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