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Synthesis method of 2, 2-diaryl acetonitrile compound

A compound and diaryl technology, applied in the field of synthesis of 2,2-diarylacetonitrile compounds, can solve the problems of harsh reaction conditions, cumbersome reaction operations, complex catalysts, etc.

Active Publication Date: 2021-09-28
LANZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Despite the above achievements, some of them still exist such as harsh reaction conditions (Chem Commun (Camb), 2017, 53, 4593-4596), complex catalysts (J.Org.Chem., 2015, 80, 10187-10196 ) and cumbersome reaction operations (Tetrahedron Lett.,2012,53,426-428) and other shortcomings
The 2,2-diaryl acetonitrile compounds involved in the present invention are a class of derivatives of diindolylmethane (BIM). Existing bibliographical reports rarely relate to this type of BIM compound. Due to the lack of synthetic methods, its potential The value of research has not been fully utilized, therefore, it is of great significance to develop the preparation method of this type of BIM compound

Method used

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  • Synthesis method of 2, 2-diaryl acetonitrile compound
  • Synthesis method of 2, 2-diaryl acetonitrile compound
  • Synthesis method of 2, 2-diaryl acetonitrile compound

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Experimental program
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Embodiment

[0021] 1. Use indole and N,N-dimethylaminomalononitrile as raw materials, and aluminum trifluoromethanesulfonate as a catalyst (reaction formula 1)

[0022]

[0023] In a pressure-resistant sealed tube, add indole (100mg, 0.85mmol), N,N-dimethylaminomalononitrile (112mg, 1.02mmol), three Aluminum fluoromethanesulfonate (81.06 mg, 0.17 mmol), under an argon atmosphere, the mixture was continuously stirred and reacted at 120° C. for 8 hours, and the reaction was completed. The reaction tube was washed with acetone and the resulting organic compound system was evaporated to dryness on a rotary evaporator and purified by column chromatography to give pure desired product as a white solid (103.06 mg, 89%).

[0024] The product detection data are as follows:

[0025] 1 H NMR (600MHz, DMSO-d 6 )δ11.17(s,2H),7.59(d,J=7.8Hz,2H),7.43–7.41 (m,4H),7.12(t,J=7.8Hz,2H),7.00(t,J=7.8 Hz,2H),6.08(s,1H); 13 C NMR (150MHz, DMSO-d 6 )δ136.54, 125.20, 123.69, 121.52, 120.68, 118.87, 118.49...

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Abstract

The invention relates to a synthesis method of a 2, 2-diarylacetonitrile compound, the synthesis method has the following reaction general formula: N, N-disubstituted aminomalononitrile and substituted aromatic hydrocarbon are subjected to a series coupling reaction under the action of a catalyst, and the 2, 2-diarylacetonitrile compound is rapidly and effectively synthesized. The method has the advantages of mild conditions, wide substrate range and convenience in operation, not only provides a new synthesis thought for synthesizing corresponding diindolylmethane (BIM) type functional molecules, but also greatly enriches a BIM compound library and promotes related activity research of the compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2,2-diaryl acetonitrile compounds. Background technique [0002] As we all know, the diindolylmethane (BIM)-type skeleton is a key structural unit, and many BIM-like compounds have different pharmacological activities, such as: anti-inflammatory, anti-oxidant, anti-bacterial, anti-hyperlipidemic, regulating hormone secretion, inducing HL60 cell differentiation activates the activity of G protein-coupled receptor GPR84; in addition, it also has the potential to become functional materials such as photoelectric materials or probes. As shown in the following selected examples: Gelliusine F (I) and 2,2-bis-(6'-bromo-3'-indolyl)-ethylamine (II) isolated from New Caledonia sponge Orina sp have anti- Serotonin activity, has a strong affinity for somatostatin and neuropeptide Y receptors; streptindole (III) is isolated from enterobacteria Stre...

Claims

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Application Information

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IPC IPC(8): C07D209/18C07D207/337C07C253/30C07C255/42
CPCC07D209/18C07D207/337C07C253/30C07C255/42
Inventor 王少华王博文雷林生
Owner LANZHOU UNIVERSITY
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