Method for synthesizing alpha-aminonitrile by adopting AIBN as individual cyan source

A technology of aminonitrile and cyano groups, applied in the field of α-aminonitrile compounds, can solve the problem that the nitrile source cannot get rid of the severe toxicity, and achieve the effect of high yield and simple method

Active Publication Date: 2017-07-14
LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are many methods for directly synthesizing α-aminonitriles, but the use of nitrile sources has not been able to get rid of the problem of severe toxicity.

Method used

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  • Method for synthesizing alpha-aminonitrile by adopting AIBN as individual cyan source
  • Method for synthesizing alpha-aminonitrile by adopting AIBN as individual cyan source
  • Method for synthesizing alpha-aminonitrile by adopting AIBN as individual cyan source

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Experimental program
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Embodiment 1-16

[0019] Synthesis method: 1.0 mol of tertiary amine 2 was added into a sealed tube, and then 3.0 mol of AIBN, 1.5 mol of pivalic acid, 1.0 mol of sodium acetate, molecular sieves, and methanol were added as solvents. The reaction was heated to 90°C for 8 hours, then cooled to room temperature, and separated by silica gel column chromatography. The flushing agent is petroleum ether / ethyl acetate (5:1 v / v). The results are shown in Table 1. The reaction formula is as follows:

[0020]

[0021] Table 1

[0022]

[0023]

[0024]

[0025]

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Abstract

The invention relates to a method for synthesizing alpha-aminonitrile by adopting AIBN as an individual cyan source. The method comprises the following steps: adding tertiary amine into a container, sequentially adding 2,2'-azodiisobutyronitrile (AIBN), pivalic acid, sodium acetate and molecular sieve, carrying out a reaction at 85-95 DEG C in methanol used as a solvent for 7-9 h, cooling the obtained reaction product to room temperature, and carrying out silica gel column chromatographic separation to obtain the target product. The AIBN is a nontoxic compound containing a cyan group, and is usually used as a free radical initiator. The method for synthesizing a series of alpha-aminonitrile compounds by adopting AIBN as the only cyan source has the advantages of simplicity, no toxicity and high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing a series of α-aminonitrile compounds with simple method and using AIBN as a nitrile source. Background technique [0002] α-Aminonitriles are not only precursors for the construction of nitrogen-containing bioactive compounds (such as α-amino acids and steroids), but also have been widely used in many fields of synthesis. This bifunctional compound exhibits dual reactivity by generating iminium ions (electrophiles) and carboxylate ions (nucleophiles), which are used in the synthesis of a variety of valuable functional groups, including α-aminoaldehydes, ketones and α- Amino Alcohol. Therefore, it is necessary to develop efficient and convenient methods for the synthesis of α-aminonitriles. [0003] [0004] At present, there are many methods for directly synthesizing α-aminonitriles, but the use of nitrile sources has been unable to get...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/42C07D207/16C07D211/60C07D265/30C07B43/08
CPCC07B43/08C07C253/00C07D207/16C07D211/60C07D265/30C07C255/42
Inventor 于芳李亚楠赵世晨何宇鹏李飞
Owner LIAONING UNIVERSITY OF PETROLEUM AND CHEMICAL TECHNOLOGY
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