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A kind of multi-substituted alkyne amidine compound and its preparation method and application

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: 2021-07-16
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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  • A kind of multi-substituted alkyne amidine compound and its preparation method and application
  • A kind of multi-substituted alkyne amidine compound and its preparation method and application
  • A kind of multi-substituted alkyne amidine compound and its preparation method and application

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Experimental program
Comparison scheme
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 a multi-substituted alkyne amidine compound, a preparation method and application thereof. In the reactor, add alkyne bromide palladium salt catalyst, additives and alkali to dissolve in the organic solvent, and finally add isonitrile and stir the reaction at 90-100°C, the reaction product is separated and purified to obtain polysubstituted alkyne amidine compounds, the above preparation The reaction formula of method is shown in formula (I). The method of the present invention synthesizes a series of multi-substituted alkyne amidine compounds with simple and easy-to-obtain alkyne bromide, amine, and isonitrile as reaction raw materials. The method has the advantages of simple and easy-to-obtain raw materials, convenient operation, mild conditions, high step economy, and It has the characteristics of wide applicability and good tolerance of functional groups; and carried out some application research, and synthesized a variety of useful nitrogen-containing heterocycles.

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 Patents(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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