Synthesizing method for 3-aroyl indole compound

An aroyl indole compound, green synthesis technology, applied in the direction of organic chemistry, etc., can solve the problem of limited use and other issues

Active Publication Date: 2015-09-30
ANHUI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Lewis acids play an important role in organic synthesis, and their use is lim

Method used

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  • Synthesizing method for 3-aroyl indole compound
  • Synthesizing method for 3-aroyl indole compound
  • Synthesizing method for 3-aroyl indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 4-methyl-β-nitrostyrene and 2-(2-pyridyl)-1H-indole, solvent ethanol

[0023]

[0024] Add CeCl to the thick-walled pressure-resistant reaction tube in sequence 3 ·7H 2 O (7.5mg, 0.02mmol), reactant A (38.8mg, 0.2mmol), reactant B (48.9mg, 0.3mmol); then add solvent ethanol 2ml, put it in 120°C oil bath for 12h. After the reaction was complete as detected by TLC, it was separated and purified by column chromatography, the developer was petroleum ether: ethyl acetate = 4:1, and the separation yield was 74.75%. 1 HNMR (400MHz, CDCl 3 ):δ11.06(s,1H),8.57(d,J=4.2Hz,1H),7.82-7.78(m,3H),7.51(td,J 1 =7.7Hz,J 2 =1.7Hz,1H),7.44(d,J=8.0Hz,1H),7.38(d,J=8.1Hz,1H),7.24-7.14(m,4H),7.10-7.06(m,1H),2.38 (s,3H); 13 CNMR (100MHz, CDCl 3 ): δ193.5, 149.1, 148.7, 143.4, 138.8, 137.0, 136.6, 135.1, 130.2, 129.0, 128.9, 124.5, 123.8, 123.1, 121.6, 121.4, 114.5, 111.5, 21.6.

Embodiment 2

[0026] (E)-N,N-Dimethyl-4-(2-nitrovinyl)aniline and 2-(2-pyridyl)-1H-indole, solvent ethanol

[0027]

[0028] Add CeCl to the thick-walled pressure-resistant reaction tube in sequence 3 ·7H 2 O (7.5mg, 0.02mmol), reactant A (38.8mg, 0.2mmol)), reactant B (57.6mg, 0.3mmol); then add solvent ethanol 2ml, put it in 120℃ oil bath for 12h. After the reaction was complete as detected by TLC, it was separated and purified by column chromatography. The developing solvent was petroleum ether: ethyl acetate = 4:1, and the separation yield was 71.72%. 1 HNMR (400MHz, CDCl 3 ):δ0.63(s,1H),8.57(d,J=4.1Hz,1H),7.87(d,J=8.6Hz,3H),7.56-7.37(m,3H),7.24-7.12(m, 2H), 7.07-7.03(m, 1H), 6.59(d, J=8.8Hz, 2H), 3.02(s, 3H); 13 CNMR (100MHz, CDCl 3 ): δ192.2, 153.4, 149.3, 148.7, 136.8, 136.6, 134.9, 132.6, 129.0, 126.7, 123.7, 123.5, 122.7, 121.5, 120.8, 115.3, 111.3, 110.5, 40.0.

Embodiment 3

[0030] 4-Chloro-β-nitrostyrene and 2-(2-pyridyl)-1H-indole, solvent ethanol

[0031]

[0032] Add CeCl to the thick-walled pressure-resistant reaction tube in sequence 3 ·7H 2 O (7.5mg, 0.02mmol), reactant A (38.8mg, 0.2mmol)), reactant B (57.7mg, 0.3mmol); then add solvent ethanol 2ml, put it in 120℃ oil bath for 12h. After the reaction was complete as detected by TLC, it was separated and purified by column chromatography. The developing solvent was petroleum ether: ethyl acetate = 4:1, and the separation yield was 82.21%. 1 HNMR (400MHz, CDCl 3 ):δ10.4(s,1H),8.6(d,J=3.2Hz),1H,7.85-7.80(m,3H),7.59-7.57(t,J=7.4Hz,1H),7.47-7.40( m,2H),7.36-7.35(m,J=8.20Hz,2H),7.29-7.21(m,2H),7.14-7.10(m,1H); 13 CNMR (100MHz, CDCl 3): δ192.2, 149.0, 148.7, 139.2, 138.9, 138.1, 136.8, 134.9, 131.4, 128.8, 128.6, 124.5, 124.1, 123.4, 121.8, 121.5, 113.8, 111.6.

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Abstract

The invention discloses a synthesizing method for a 3-aroyl indole compound as shown in the following formula (C). The synthesizing method is characterized in that R1 replacing indole (A) and R2 replacing nitroalkene serve as raw materials, cerium salt serves as a catalyst, and in an air environment, acylation reaction is performed. According to the synthesizing method for the 3-aroyl indole compound, the more stable and cheaper cerium salt is adopted to serve as the catalyst, absolute non-water processing does not need to be performed in the reaction, inert gases are not needed for protection, that is, the acylation reaction can be directly performed, the reaction condition is milder, and the yield is high.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a R 1 Substituted 2-(2-pyridyl)-1H-indole with R 2 A substituted nitroalkene is catalyzed by a rare earth metal catalyst, and undergoes an acylation reaction in an air environment to directly prepare a green synthetic method for 3-aroyl indole compounds. Background technique [0002] Indole compounds are important alkaloids. Indole structural units are widely found in various natural products and drugs, and have various biological activities. Especially 3-aroyl indole compounds, which can be used as platelet activating factor anticoagulants, microtubule inhibitors, and commercially available pravodoline with analgesic and anti-inflammatory effects and rameosetron hydrochloride with antiemetic effects. [0003] The traditional methods for synthesizing 3-acylated indole mainly include (1) Friedel–Crafts reaction, (2) Vilsmeier–Haack reaction, (3) reaction of bicycloalkene or N-(...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 李忠朱慧芝冯承涛罗再刚钱元元吴松松
Owner ANHUI UNIV OF SCI & TECH
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