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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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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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-indole-3-ones using 2-methyl-1H-indole Compound, using dimethyldioxirane (DMD) as oxidant, but the yield of this method is less than 10% (J.Am.Chem.Soc.1993,115,8867.)

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

Embodiment 1

[0016]

[0017] In a 10mL reaction tube, add 48.0mg (0.2mmol) N-(2-acetylphenyl) pyridine amide, 11.4mg (0.06mmol) cuprous iodide, 24.0mg (0.4mmol) acetic acid, 1.5mL dimethyl sulfoxide, the reaction tube was evacuated, magnetically stirred, and reacted at 100°C for 5 hours in an oxygen atmosphere. TLC monitors that the reaction is complete, wait for the reaction solution to cool to room temperature, extract 3 times with ethyl acetate, wash the organic phase with saturated saline solution, then dry with anhydrous sodium sulfate, concentrate by distillation under reduced pressure, and separate by column chromatography (the eluent is Petroleum ether and ethyl acetate volume ratio 5:1 mixed liquor), obtain target product 2a, chemical name is 2-hydroxyl-indol-3-one, and its yield is 77%, and structural characterization data is as follows:

[0018] 1 H NMR (400MHz, Chloroform-d) δ8.70–8.61(m,2H),8.40(s,1H),8.30(dt,J=8.0,1.1Hz,1H),8.04(td,J=7.8,1.8 Hz,1H),7.88–7.82(m,1H),7.79–7...

Embodiment 2

[0020]

[0021] In the present embodiment, replace the N-(2-acetylphenyl) pyridine amide used in embodiment 1 with the N-(2-acetyl group-6-methylphenyl) pyridine carboxylic acid amide of equimolar amount, other The steps were the same as in Example 1 to obtain the target product 2b with a yield of 60%, and the structural characterization data are as follows:

[0022] 1 H NMR (400MHz, Chloroform-d) δ8.70(d, J=4.1Hz, 1H), 8.33(d, J=7.9Hz, 1H), 8.02(td, J=7.8, 1.8Hz, 1H), 7.68 (d,J=7.0Hz,1H),7.65–7.60(m,1H),7.58(d,J=7.5Hz,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 h 13 N 2 o 3 [M+H] + , The theoretical value is 269.0921, and the measured value is 269.0922.

Embodiment 3

[0024]

[0025] In the present embodiment, replace the N-(2-acetylphenyl) pyridine amide used in embodiment 1 with N-(2-acetyl-5-methylphenyl) pyridine carboxylic acid amide of equimolar amount, other The steps were the same as in Example 1 to obtain the target product 2c with a yield of 76%, and the structural characterization data are as follows:

[0026] 1 H NMR (400MHz, Chloroform-d) δ8.65 (d, J = 4.5Hz, 1H), 8.47 (s, 1H), 8.38–8.25 (m, 2H), 8.03 (td, J = 7.8, 1.8Hz, 1H), 7.72(d, J=7.8Hz, 1H), 7.64–7.58(m, 1H), 7.13(d, J=7.8Hz, 1H), 5.57(s, 1H), 2.52(s, 3H); 13 C NMR (100MHz, 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 h 13 N 2 o 3 [M+H] + , The theoretical value is 269.0921, and the measured value is 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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