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2-cyanoindole substituted gem-difluoroolefin compound as well as preparation method and application thereof

A technology of gem-difluoroalkene and cyanoindole, which is applied in the field of 2-cyanoindole-substituted gem-difluoroalkene compound and its preparation, can solve the problems of substrate reaction limitations and achieve simple operation and mild reaction conditions , the effect of high yield

Pending Publication Date: 2021-10-22
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, indole-substituted gem-difluoroalkene methods are very rare (Angew.Chem.Int.Ed.2020,59,5572–5576), these prior art methods usually require the use of explosive azo compounds, and the substrate reaction More limited, usually limited to N-alkylated electron-rich indole substrates, while those with electron-withdrawing functional groups such as ester groups and cyano groups cannot react
And 2-cyanoindole substituted gem-difluoroalkene compound and its synthetic method, then there is no bibliography at present

Method used

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  • 2-cyanoindole substituted gem-difluoroolefin compound as well as preparation method and application thereof
  • 2-cyanoindole substituted gem-difluoroolefin compound as well as preparation method and application thereof
  • 2-cyanoindole substituted gem-difluoroolefin compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The reaction equation is:

[0041]

[0042] Take a 25mL round bottom flask, add trifluoromethylindolemethanol 2a (87.4mg, 0.3mmol), magnesium oxide (3mmol), scandium trifluoromethanesulfonate (0.06mmol), trimethylsilyl cyanide (0.9mmol) in sequence , anhydrous chlorobenzene (3mL), stirred at 120°C for 12 hours (thin plate chromatography tracked the reaction until the reaction was complete), cooled to room temperature after the reaction, filtered to remove insolubles, and the filtrate was spun and concentrated to remove the solvent, with a volume ratio of 25: A 1-10:1 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain the target product 1a (63.1 mg, white solid, yield 75%).

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

[0044] figure 2 The carbon nuclear magnetic resonance spectrum of the compound 1a prepared for the present embodiment;

[...

Embodiment 2

[0049] The reaction equation is:

[0050]

[0051] Take a 25mL round bottom flask, add trifluoromethylindolemethanol 2b (91.6mg, 0.3mmol), magnesium oxide (3mmol), scandium trifluoromethanesulfonate (0.06mmol), trimethylsilyl cyanide (0.9mmol) in sequence , anhydrous chlorobenzene (3mL), stirred at 120°C for 8 hours (thin plate chromatography tracked the reaction until the reaction was complete), cooled to room temperature after the reaction, filtered to remove insolubles, and the filtrate was spun and concentrated to remove the solvent, with a volume ratio of 25: A 1-10:1 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain the target product 1b (70.6 mg, white solid, yield 80%).

[0052] 1 H NMR (400MHz, CDCl 3 )δ8.98(s,1H),7.36–7.30(m,6H),7.22(d,J=8.5Hz,1H),7.05(s,1H),2.37(s,3H); 13 C NMR (101MHz, CDCl 3 )δ153.9(dd, J=296.9,293.9Hz),135.2,132.7(dd,J=5.1,3.0Hz),128.8(dd,J=4.0,3.0Hz),128.6128.5,127.8,125.8(d,J = 2.0...

Embodiment 3

[0054] The reaction equation is:

[0055]

[0056] Take a 25mL round bottom flask, add trifluoromethylindolemethanol 2c (104.8mg, 0.3mmol), magnesium oxide (3mmol), scandium trifluoromethanesulfonate (0.06mmol), trimethylsilyl cyanide (0.9mmol) in sequence , anhydrous chlorobenzene (3mL), stirred at 120°C for 24 hours (thin plate chromatography followed the reaction until the reaction was complete), cooled to room temperature after the reaction, filtered to remove insolubles, and the filtrate was spun and concentrated to remove the solvent, with a volume ratio of 20: A 1-5:1 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain the target product 1c (52.8 mg, white solid, yield 52%).

[0057] 1 H NMR (600MHz, CDCl 3 )δ9.41(s,1H),8.08–8.06(m,2H),7.45(d,J=9.3Hz,1H),7.36–7.29(m,5H),3.90(s,3H); 13 C NMR (151MHz, CDCl 3 )δ167.5, 154.0 (dd, J = 299.0, 293.7Hz), 139.1, 132.3 (dd, J = 4.6, 3.0Hz), 128.7 (t, J = 3.5Hz), 128.6, ...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a 2-cyanoindole substituted gem-difluoroolefin compound and a preparation method and application thereof. The preparation method of the compound comprises the steps: taking a trifluoromethylindole methanol compound and trimethylsilyl cyanide as raw materials, and under the action of a Lewis acid catalyst and inorganic alkali, carrying out a heating reaction in a solvent to obtain a 2-cyanoindole substituted gem-difluoroolefin compound. The invention provides the 2-cyanoindole substituted gem-difluoroolefin compound and the preparation method thereof. According to the method, the trifluoromethyl indole methanol compound and the trimethylsilyl cyanide which are simple and easy to obtain are used as raw materials, explosive diazo compounds do not need to be used, and the 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 a gem-difluoroalkene compound substituted by 2-cyanindole and its preparation method and application. Background technique [0002] Gem-difluoroolefin compounds are widely used in the fields of drugs, pesticides, insecticides and functional materials. Gem-difluoroalkenes are considered to be biological isoelectronics of carbonyl compounds. Many natural products and drugs with biological activity can significantly enhance their physiological and pharmacological activities by introducing gem-difluoro-alkene units, such as Artemisia annua containing gem-difluoroalkenes The peptide derivatives showed more excellent biological activity. In addition, gem-difluoroalkenes are also very important organic synthesis intermediates, which can be used to synthesize various fluorine-containing and non-fluorine-containing functional molecules. For example, gem-difluoroalkenes can be e...

Claims

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Application Information

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IPC IPC(8): C07D209/42C07D409/06C07D209/14C07D471/04
CPCC07D209/42C07D409/06C07D209/14C07D471/04
Inventor 饶卫东桑静静包晴胡睿陈继超
Owner NANJING FORESTRY UNIV
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