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Poly-substituted alkynyl amidine compounds, preparation method and application thereof

A compound and multi-substitution technology, applied in the field of multi-substituted alkyne amidine compounds and their preparation, can solve problems such as few studies, and achieve the effects of convenient operation, simple and easy-to-obtain raw materials, and novel and efficient synthesis method.

Active Publication Date: 2019-10-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the current extensive research on the insertion of isocyanides into arylpalladium and alkenylpalladium species, chemists have rarely studied the combination of isocyanide and alkynepalladium species

Method used

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  • Poly-substituted alkynyl amidine compounds, preparation method and application thereof
  • Poly-substituted alkynyl amidine compounds, preparation method and application thereof
  • Poly-substituted alkynyl amidine compounds, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] Add 0.2 mmol of aniline, 0.3 mmol of triisopropylsilyl alkyne bromide, 0.02 mmol of palladium chloride, 0.4 mmol of potassium carbonate, 0.04 mmol of silver trifluoroacetate, and 2 ml of acetonitrile solvent into the reaction tube, and finally Add 0.25 mmol tert-butyl isonitrile, stir and react at 100° C. at 700 rpm for 4 hours, and stop stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product, which is eluted by column chromatography The liquid is petroleum ether:ethyl acetate mixed solvent with a volume ratio of 100:1, and the yield is 85%.

[0047] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows figure 1 and figure 2 shown; the structural characterization data are shown below:

[0...

Embodiment 2

[0055] In the reaction tube, add 0.2 mmol 4-phenoxyaniline, 0.3 mmol triisopropylsilyl alkyne bromide, 0.02 mmol palladium chloride, 0.4 mmol potassium carbonate, 0.04 mmol silver trifluoroacetate, and 2 Milliliter of acetonitrile solvent, finally add 0.25 mmol tert-butyl isonitrile, stir the reaction at 100 degrees Celsius at 700 rpm for 4 hours, stop stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product, which is eluted by column chromatography The liquid is petroleum ether with a volume ratio of 60:1: ethyl acetate mixed solvent, and the yield is 70%.

[0056] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows image 3 and Figure 4 shown; the structural characterization data are shown belo...

Embodiment 3

[0064] Add 0.2 mmol 4-iodoaniline, 0.3 mmol triisopropylsilyl alkyne bromide, 0.02 mmol palladium chloride, 0.4 mmol potassium carbonate, 0.04 mmol silver trifluoroacetate, and 2 mL acetonitrile to a reaction tube Solvent, finally add 0.25 mmol tert-butyl isonitrile, stir and react at 100 degrees Celsius at 700 rpm for 4 hours, and stop stirring. Add 5 mL of water, extract 3 times with ethyl acetate, combine the organic phases and use 0.5 g of anhydrous sodium sulfate to dry, filter, concentrate under reduced pressure, and then separate and purify by column chromatography to obtain the target product, which is eluted by column chromatography The liquid is sherwood oil with a volume ratio of 80:1: ethyl acetate mixed solvent, and the yield is 84%.

[0065] The hydrogen spectrogram and the carbon spectrogram of the product obtained in this embodiment are respectively as follows Figure 5 and Figure 6 shown; the structural characterization data are shown below:

[0066] 1 H ...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses poly-substituted alkynyl amidine compounds, a preparation method and an application thereof. The preparation method includes adding and dissolving an alkynyl bromide palladium salt catalyst, an additive and alkali in an organic solvent in a reactor, finally, adding isonitrile and stirring the mixture to react at 90-100 DEG C, and separating and purifying the reaction product to obtain the poly-substituted alkynyl amidine compounds, wherein the reaction formula is shown in a formula (I). The method uses simple andeasily available alkynyl bromide, amine and isonitrile as reaction raw materials to synthesize a series of poly-substituted alkynyl amidine compounds. The method has the characteristics of simple andeasily-available raw materials, convenient operation, mild conditions, high step economy, wide substrate applicability, good tolerance of functional groups and the like; and some of application studies of the method are carried out and a variety of useful nitrogen-containing heterocycles are synthesized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a multi-substituted alkyne amidine compound and its preparation method and application. Background technique [0002] Multi-substituted alkyne amidines have rich chemical properties due to the simultaneous carbon-carbon triple bond and amidine functional groups. In addition to participating in the construction of various heterocyclic compounds as efficient synthons, alkyne amidines can also be used as ligands to participate in the design and synthesis of new catalysts. Through literature research, the current main synthetic methods include: (1) addition reaction of terminal alkynes and bulky carbodiimides; (2) 1,4- Metallolysis reactions (W.-X.Zhang, M.Nishiura, Z.Hou, J.Am.Chem.Soc.2005, 127, 16788; T.-G.Ong, J.S.O'Brien; I.Korobkov, D.S. Richeson, Organometallics 2006, 25, 4728; W. Yi, J. Zhang, M. Li, Z. Chen, X. Zhou, Inorg. Chem. 2011, 50, 11813; X. G...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C07D249/04C07D215/38
CPCC07D215/38C07D249/04C07F7/10Y02P20/55
Inventor 伍婉卿李蒙江焕峰
Owner SOUTH CHINA UNIV OF TECH
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