Synthesis method of 2-hydroxy-indole-3-ketone compound

A technology of ketone compounds and synthetic methods, which is applied in the direction of organic chemistry, can solve the problems of low yield, and achieve the effects of high yield, cost saving, and mild reaction conditions

Active Publication Date: 2021-08-20
YANAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In recent years, few articles have reported the synthesis of 2-hydroxy-indole-3-one compounds. Foote’s research group proposed a method to synthesize 2-hydroxy-

Method used

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  • Synthesis method of 2-hydroxy-indole-3-ketone compound
  • Synthesis method of 2-hydroxy-indole-3-ketone compound
  • Synthesis method of 2-hydroxy-indole-3-ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0015] Example 1

[0016]

[0017] 48.0 mg (0.2 mmol) of N- (2-acetyl) pyridinamide, 11.4 mg (0.06 mmol) of iodide, 24.0 mg (0.4 mmol) acetic acid, 1.5 ml (0.4 mmol) of acetic acid, 1.5 ml (0.4 mmol) The base is sulfoxide, and the reaction tube is vacuum, magnetic stirring, in an oxygen atmosphere, and at 100 ° C for 5 hours. The TLC was monitored completely, and the reaction solution was cooled to room temperature, extracted 3 times with ethyl acetate, washed with a saturated brine solution, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure (eluent The hydroof ether and the mixture of ethyl acetate were 5: 1), resulting in a target product 2a, chemically named 2-hydroxy-indole-3-ketone, its yield is 77%, and the structural characterization data is as follows:

[0018] 1 H NMR (400 MHz, ChlorOform-D) δ8.70-8.61 (m, 2H), 8.40 (S, 1H), 8.30 (DT, J = 8.0, 1.1 Hz, 1H), 8.04 (TD, J = 7.8, 1.8 Hz, 1H), 7.88-7.82 (m, 1H), 7.79-7.72 (m, 1H), 7.65-7.58 (m,...

Example Embodiment

[0019] Example 2

[0020]

[0021] In the present embodiment, the N- (2-acetylphenyl) pyridin amide used in Example 1 was replaced with an equimolar N- (2-acetyl-6-methylphenyl) pyridic acid amide. The step is the same as that of Example 1, resulting in the target product 2b, with a yield of 60%, and the structural characterization data is as follows:

[0022] 1 H NMR (400MHz, Chloroform-D) Δ8.70 (D, J = 4.1 Hz, 1H), 8.33 (D, J = 7.9 Hz, 1H), 8.02 (TD, J = 7.8, 1.8 Hz, 1H), 7.68 (D, J = 7.0 Hz, 1H), 7.65-7.60 (m, 1H), 7.58 (D, J = 7.5 Hz, 1H), 7.34-7.24 (m, 2H), 5.43 (S, 1H), 2.35 ( s, 3h); 13 C NMR (100MHz, Chloroform-D) δ195.20, 164.88, 152.27, 151.15, 148.02, 139.84, 138.49, 130.77, 127.42, 126.36, 126.19, 125.70, 122.25, 83.12, 20.76; HRMS C 15 Hide 13 N 2 O 3 [M + h] + , Theoretical value 269.0921, measured value 269.0922.

Example Embodiment

[0023] Example 3

[0024]

[0025] In this embodiment, the N- (2-acetylphenyl) pyridin amide used in Example 1 was replaced with an equimolar amount of N- (2-acetyl-5-methylphenyl) pyridamide. The step is the same as that of Example 1, resulting in the target product 2c, with a yield of 76%, and the structural characterization data is as follows:

[0026] 1 H NMR (400MHz, Chloroform-D) δ8.65 (D, J = 4.5 Hz, 1H), 8.47 (S, 1H), 8.38-8.25 (m, 2H), 8.03 (TD, J = 7.8, 1.8 Hz, 1H), 7.72 (D, J = 7.8 Hz, 1H), 7.64-7.58 (m, 1H), 7.13 (D, J = 7.8 Hz, 1H), 5.57 (S, 1H), 2.52 (S, 3H); 13 C NMR (100 MHz, Chloroform-D) δ193.92, 164.45, 153.13, 151.90, 149.65, 147.26, 138.80, 126.97, 126.67, 124.41, 121.04, 119.76, 82.04, 22.84; HRMS C 15 Hide 13 N 2 O 3 [M + h] + , Theoretical value 269.0921, measured value 269.0919.

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Abstract

The invention discloses a synthesis method of a 2-hydroxy-indole-3-ketone compound, which comprises the steps of by taking N-(2-acetylphenyl) pyridineamide and a derivative thereof as raw materials, cuprous iodide and other copper salts as catalysts and acetic acid and the like as additives, reacting at the temperature of 80-110 DEG C in an oxygen atmosphere to obtain the 2-hydroxy-indole-3-ketone compound. The method has the characteristics of good substrate applicability, atom economy, easiness in operation, avoidance of substrate preparation, low reagent cost, cost saving, mild reaction conditions, one-step synthesis, high yield and the like, and a new strategy is provided for synthesis of the 2-hydroxy-indole-3-ketone compound.

Description

technical field [0001] The present invention relates to the synthesis of 2-hydroxyl-indol-3-ketone compounds, in particular to the use of N-(2-acetylphenyl)pyridinoline amide and its derivative 1 as raw materials, under the catalysis of cuprous iodide , to prepare 2-hydroxyl-indol-3-one compounds, in this reaction, N-(2-acetylphenyl) pyridinoline amide and its derivatives 2 are under the oxidation of cuprous iodide and oxygen, 2-Hydroxy-indol-3-ones were synthesized through pyridine-directed ring closure and copper chelation. Background technique [0002] Indole is the most common heterocycle in nature, which exists in a variety of bioactive compounds and indole-derived drug molecules. Among the numerous indole skeletons, indol-3-ones are ubiquitous structures in drugs and natural products, and they are also widely used in fluorescent dyes and solar cells. In particular, the construction of 2-hydroxy-indol-3-ones with a quaternary carbon center at the C2 position has arous...

Claims

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Application Information

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IPC IPC(8): C07D401/06C07D403/06
CPCC07D401/06C07D403/06
Inventor 马豪杰郭翠张玉琦王记江
Owner YANAN UNIV
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