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A class of (z)-2-thio-β-aminocrotononitrile compounds and their electrochemical preparation methods

An aminocrotononitrile and compound technology, which is applied in the field of electrochemical organic synthesis, can solve the problem that compound synthesis work has not been reported, and achieve the effects of simple and efficient reaction system, high yield and wide application range.

Active Publication Date: 2020-05-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, so far, the synthesis of such compounds has not been reported

Method used

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  • A class of (z)-2-thio-β-aminocrotononitrile compounds and their electrochemical preparation methods
  • A class of (z)-2-thio-β-aminocrotononitrile compounds and their electrochemical preparation methods
  • A class of (z)-2-thio-β-aminocrotononitrile compounds and their electrochemical preparation methods

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] With metal platinum sheet as anode and platinum wire as cathode, add 0.5mmol tetra-n-butylammonium perchlorate, 0.05mmol tartaric acid, 0.1mmol (1,2-bis(diphenylphosphino)ethyl alkane), 0.25mmol potassium iodide, 0.5mmol p-fluorothiophenol, 5mL acetonitrile, a magnetic stirrer, cover the lid, turn on the power, adjust the current to 10mA, and electrolyze for 6h at room temperature. After the reaction, the reaction solution was extracted with ethyl acetate, and the corresponding product 3a was obtained after separation and purification, and the yield of the product 3a was 91%. The reaction scheme of the present embodiment is as follows:

[0042]

[0043] The proton nuclear magnetic resonance spectrum of the product of this embodiment is as follows: figure 1 Shown: 1 H NMR (400MHz, CDCl 3 ):δ7.24–7.19(m,2H),7.00–6.96(m,2H),5.66(br s,2H),2.27(s,3H); figure 2 Shown: 13 C NMR (100MHz, CDCl 3 ):δ164.9,161.7(d,J C-F =246.0Hz), 130.4(d, J C-F =3.2Hz), 128.5(d, J C-...

Embodiment 2

[0045] With metal platinum mesh as anode and platinum sheet as cathode, add 0.5mmol tetra-n-butylammonium perchlorate, 0.05mmol citric acid, 0.1mmol bis(diphenylphosphino)methane, 0.3mmol iodine Ammonium chloride, 0.5mmol p-fluorothiophenol, 5mL acetonitrile, a magnetic stirrer, cover the lid, turn on the power, adjust the current to 15mA, and electrolyze at room temperature for 8h. After the reaction, the reaction liquid was extracted with ethyl acetate, and the corresponding product 3a was obtained after separation and purification, and the yield of the product 3a was 85%. The reaction scheme of the present embodiment is as follows:

[0046]

Embodiment 3

[0048] With metal platinum mesh as anode and platinum wire as cathode, add 0.5mmol tetra-n-butylammonium perchlorate, 0.05mmol citric acid, 0.1mmol 1,2-bis(diphenylphosphino)ethyl Alkanes, 0.35mmol potassium iodide, 0.5mmol p-fluorothiophenol, 5mL acetonitrile, a magnetic stirrer, cover the lid, turn on the power, adjust the current to 10mA, and electrolyze for 4h at room temperature. After the reaction, the reaction solution was extracted with ethyl acetate, and the corresponding product 3a was obtained after separation and purification, and the yield of the product 3a was 92%. The reaction scheme of the present embodiment is as follows:

[0049]

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Abstract

The invention discloses a (Z)-2-sulpho-beta-aminocrotononitrile compound and an electrochemical preparation method thereof, and belongs to the technical field of electrochemical organic synthesis. Thepreparation method comprises the following steps that electrolyte, a sulfur source, an iodine source, acid, organic phosphorus and electrolytic solvents are added into an electrolytic tank without amembrane; an anode and a cathode are inserted; stirring and electrification are performed; reaction is performed under the constant current condition; after the reaction is completed, electrolyte is subjected to organic extraction by an organic solvent; then, separation and purification are performed to obtain the (Z)-2-sulpho-beta-aminocrotononitrile compound. The electrode used by the method isa general inert electrode; the electrode modification is not needed; the additional addition of metal catalysts is not needed; cheap and easy-to-obtain thiophenol (or mercaptan and disulfide) and acetonitrile are used as raw materials; the yield is high; the selection is high; the reaction system is simple and effective; the environment-friendly effect is achieved. The method has the advantages that the reaction is operated at normal temperature and normal pressure; simplicity and safety are realized; the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of electrochemical organic synthesis, and specifically relates to a class of (Z)-2-thio-β-aminocrotononitrile compounds and an electrochemical preparation method thereof. Background technique [0002] Sulfur-containing organic compounds are an important class of organic compounds that widely exist in natural products, pharmaceuticals, pesticides and organic compounds with biological activity. β-Aminocrotononitrile is an important core skeleton, and its special structure makes it often used as an important intermediate in the synthesis of heterocyclic compounds. The (Z)-2-thio-β-aminocrotononitrile compounds in the present invention have the core skeletons of the above two types of compounds, and can complete a series of derivatization through functional groups such as double bonds, amino groups, and cyano groups contained in the structure itself. Transformation has great synthetic application value. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/58C25B3/00
CPCC07C323/58C25B3/00
Inventor 黄精美何天骏
Owner SOUTH CHINA UNIV OF TECH
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