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Trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound as well as preparation method and application thereof

A technology of trifluoromethyl all-carbon quaternary carbon and fluoromethyl indole alcohol, which is applied in the field of indole acetonitrile compounds containing trifluoromethyl all-carbon quaternary carbon centers and its preparation, and can solve the problems of synthesis without literature reports, etc. Achieve the effects of wide reaction substrate range, strong inhibitory effect and high yield

Active Publication Date: 2021-11-30
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, there are many synthetic methods of indole acetonitrile compounds, such as the nucleophilic substitution reaction of halides and highly toxic inorganic cyanides, etc., but the synthesis of indole acetonitrile compounds containing trifluoromethyl all-carbon quaternary carbon centers is still not yet available. No literature report

Method used

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  • Trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound as well as preparation method and application thereof
  • Trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound as well as preparation method and application thereof
  • Trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The reaction equation is as follows:

[0040]

[0041] Take a 10mL round bottom flask, add trifluoromethyl indole alcohol 2a (0.3mmol), tris(pentafluorophenyl)borane (0.03mmol), add chlorobenzene (3mL), trimethylsilyl cyanide (0.9mmol) in turn ), stirred and reacted at 120°C for 8 hours (thin plate chromatography tracked the reaction until the reaction was complete), after the reaction was completed, cooled to room temperature, the reaction mixture was concentrated by rotary evaporation to remove the solvent, and the crude product was separated by silica gel column chromatography (eluent was petroleum ether : ethyl acetate=25 / 1~8 / 1, V / V), the target product 1a (89.2 mg, white solid, yield 99%) was obtained.

[0042] figure 1 The proton nuclear magnetic resonance spectrum figure of the compound 1a prepared for embodiment;

[0043] figure 2 The carbon nuclear magnetic resonance spectrum of the compound 1a prepared for the embodiment;

[0044] image 3 The fluorine ...

Embodiment 2

[0048] The reaction equation is as follows:

[0049]

[0050] Take a 10mL round bottom flask, add trifluoromethylindole alcohol 2b (0.3mmol), tris(pentafluorophenyl)borane (0.03mmol), add chlorobenzene (3mL), trimethylsilyl cyanide (0.9mmol) in turn ), stirred and reacted at 120°C for 15 hours (thin plate chromatography tracked the reaction until the reaction was complete), after the reaction was finished, cooled to room temperature, the reaction mixture was concentrated by rotary evaporation to remove the solvent, and the crude product was separated by silica gel column chromatography (eluent was petroleum ether : ethyl acetate=25 / 1~8 / 1, V / V), the target product 1b (91.9 mg, white solid, yield 99%) was obtained.

[0051] 1 H NMR (600MHz, CDCl 3 )δ8.69(s,1H),7.50(d,J=7.6Hz,2H),7.47–7.43(m,1H),7.43–7.33(m,3H),7.19(d,J=8.2Hz,1H ),7.12(td,J=8.0,4.8Hz,1H),6.66(dd,J=11.0,7.8Hz,1H); 13 C NMR (101MHz, CDCl 3 )δ155.4(d, J=248.6Hz), 138.8(d, J=10.4Hz), 132.5(d, J=1.2Hz), 129.5,...

Embodiment 3

[0053] The reaction equation is as follows:

[0054]

[0055] Take a 10mL round bottom flask, add trifluoromethyl indole alcohol 2c (0.3mmol), tris(pentafluorophenyl)borane (0.03mmol), add chlorobenzene (3mL), trimethylsilyl cyanide (0.9mmol) in turn ), stirred and reacted at 120°C for 12 hours (thin plate chromatography tracked the reaction until the reaction was complete), after the reaction was finished, cooled to room temperature, the reaction mixture was concentrated by rotary evaporation to remove the solvent, and the crude product was separated by silica gel column chromatography (eluent was petroleum ether : ethyl acetate=25 / 1~8 / 1, V / V), the target product 1c (90.7 mg, white solid, yield 99%) was obtained.

[0056] 1 H NMR (400MHz, CDCl 3 )δ8.39(s,1H),7.62(d,J=7.3Hz,2H),7.49–7.33(m,4H),7.29(d,J=8.3Hz,1H),7.07(d,J=8.3 Hz,1H),6.95(s,1H),2.32(s,3H); 13 C NMR (101MHz, CDCl 3 )δ134.5, 131.6, 130.1, 129.6, 128.8, 128.4, 124.8, 124.7, 124.1(q, J=2.6Hz), 123.8(q, J=286...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound as well as a preparation method and application thereof. The preparation method of the compound comprises the following steps: by taking a trifluoromethyl indole alcohol compound and trimethylsilyl cyanide as raw materials, conducting heating and reacting in a solvent under the catalytic action of a Lewis acid catalyst to obtain the trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound. According to the synthetic method of the trifluoromethyl-containing all-carbon quaternary carbon center indole acetonitrile compound, a trifluoromethyl indole alcohol compound and trimethylsilyl cyanide which are simple and easy to obtain are used as raw materials, tris(pentafluorophenyl)borane is used as a catalyst, a metal catalyst and highly toxic inorganic cyanide are not needed to be used as a cyanide source, and the synthetic method has the advantages of being mild in reaction condition, easy to operate, high in yield, wide in reaction substrate range and the like.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an indole acetonitrile compound containing a trifluoromethyl all-carbon quaternary carbon center and a preparation method and application thereof. Background technique [0002] Indole acetonitrile compounds are considered to be biological metabolites of tryptophan, an important class of indole alkaloids, which widely exist in natural products, and are widely used as plant growth regulators with diverse biological activities. For example, compound A, compound B (Arvelexin) and compound C are all natural products extracted from the root of Radix isatidis. Compound A and compound B (Arvelexin) have good inhibitory effect on influenza virus (H3N2), and their IC 50 3.70, 12.35μM, respectively. In addition, studies have also found that 4-methoxyindoleacetonitrile (Compound B, Arvelexin) also has the effect of treating colitis. C6-hydroxyglucoside indoleacetonitrile (compou...

Claims

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Application Information

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IPC IPC(8): C07D209/18C07D409/06C07D209/14C07D209/16A01N43/38A01P3/00
CPCC07D209/18C07D409/06C07D209/14C07D209/16A01N43/38
Inventor 饶卫东桑静静冯丽商丹丹胡睿
Owner NANJING FORESTRY UNIV
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