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A kind of amino-substituted conjugated enyne aldehyde/ketone compound and preparation method thereof

A technology of conjugated enyne ketones and compounds, applied in the field of amino-substituted conjugated enyne aldehyde/ketone compounds and their preparation

Inactive Publication Date: 2020-11-27
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there are no literature and related patent reports on the efficient synthesis of amino-substituted conjugated enyne aldehyde ketones.

Method used

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  • A kind of amino-substituted conjugated enyne aldehyde/ketone compound and preparation method thereof
  • A kind of amino-substituted conjugated enyne aldehyde/ketone compound and preparation method thereof
  • A kind of amino-substituted conjugated enyne aldehyde/ketone compound and preparation method thereof

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preparation example Construction

[0039] The present invention also provides a preparation method of an amino-substituted conjugated enylenal / ketone compound, comprising:

[0040] Under the protection of nitrogen, react 1,4-diynyl-3-alcohol with N-fluorobisbenzenesulfonimide under the action of organic solvent and copper catalyst to obtain amino-substituted conjugated enyneal / Ketone compounds.

[0041] According to the present invention, the molar ratio of 1,4-diynyl-3-ol to N-fluorobisbenzenesulfonimide is preferably 1:(1.2-2.5), more preferably 1:2.

[0042] According to the present invention, the reaction temperature is preferably 40-70°C, more preferably 50°C; the reaction time is preferably 12-20 hours, more preferably 16 hours.

[0043] According to the present invention, the copper catalyst is preferably cuprous cyanide, and the added amount of the copper catalyst is preferably 5-20% of 1,4-diynyl-3-ol, more preferably 10%.

[0044] According to the present invention, the organic solvent is preferabl...

Embodiment 1

[0050]

[0051] Under nitrogen protection, add 1a (0.2mmol), cuprous cyanide (10mol%) as a catalyst, anhydrous chloroform (2ml), 4-acetylpyridine (0.3mmol) into a 10mL pressure-resistant tube with a magnetic stirring device , stirred at room temperature for 5min, after that, added NFSI (0.4mmol) to the system, Molecular sieve 0.2g was used as an additive, the reaction was placed at 50°C and stirred for 16h, and the completion of the reaction was detected by TLC, the reaction was quenched with saturated NaCl (10ml), extracted with dichloromethane (3×10ml), the organic phases were combined, and anhydrous sodium sulfate Dry, filter with suction, and evaporate under pressure to remove the organic solvent. Finally, through silica gel column chromatography, the nitrogen-substituted conjugated enylenal compound 2a was obtained with a yield of 76%. 2a 1 NMR spectra of H-NMR and 13 The nuclear magnetic resonance spectra of C-NMR are as follows figure 1 and figure 2 shown.

[...

Embodiment 2

[0055] Replace 1a in the example with 1b, other conditions are the same as Example 1, obtain compound 2b, productive rate is 86%, 2b 1 NMR spectra of H-NMR and 13 The nuclear magnetic resonance spectra of C-NMR are as follows image 3 and Figure 4 shown.

[0056]

[0057] Spectral analysis data 2b

[0058] 1 H NMR (600MHz, CDCl 3 )δ9.60(s,1H),8.11(d,J=7.8Hz,4H),7.50–7.46(m,4H),7.42–7.39(t,J=7.8Hz,4H),7.30(d,J =7.8Hz, 2H), 7.22(d, J=7.8Hz, 2H), 7.09(d, J=7.8Hz, 2H), 2.44(s, 3H), 2.37(s, 3H). 13 C NMR (150MHz, CDCl 3 ( / z): Calcd for C 31 h 25 NNaO 5 S 2 ,([M+Na] + ),578.1066,found 578.1080.

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Abstract

The invention provides an amido-substituted conjugated eneyne aldehyde / ketone compound and a preparation method thereof, and belongs to the technical field of organic synthetic chemistry. The amido-substituted conjugated eneyne aldehyde / ketone compound adopts a structural formula shown as a formula I. The invention further provides the preparation method of the amido-substituted conjugated eneynealdehyde / ketone compound. The amido-substituted conjugated eneyne aldehyde / ketone compound is prepared according to the following step: with N-fluorobisbenzenesulfonimide and an easily prepared 1,4-dialkynyl-3-ol as synthesis raw materials, a tandem free radical amination-alkynyl migration reaction is performed under the catalysis of copper so as to synthesize an amido-substituted conjugated eneyne aldehyde / ketone structural unit by one step. By the preparation method, raw material reagents are easy to obtain, a condition is mild, a reaction system is environmentally friendly, and a product iseasily separated and purified; the preparation method is applicable to synthesis of a variety of amido-substituted conjugated eneyne aldehyde / ketone compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to an amino-substituted conjugated enyne aldehyde / ketone compound and a preparation method thereof. Background technique [0002] Organic nitrogen-containing compounds widely exist in natural products and bioactive drug molecules, so the introduction of nitrogen-containing functional groups into simple and easy-to-obtain starting materials to synthesize complex and useful bioactive molecules has attracted widespread attention from organic synthesis workers (S.H.Cho , J.Y. Kim, J. Kwak and S. Chang, Chem. Soc. Rev., 2011, 40, 5068.). Amino-substituted conjugated enyne aldehydes / ketones can be used as effective organic synthesis intermediates to undergo various corresponding conversions, and to synthesize important organic nitrogen-containing compounds, which play a very important role in medicinal chemistry, biochemistry and materials science. role. T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/48C07C303/40
CPCC07C303/40C07C311/48
Inventor 李燕张前孙佳琼郑光范杨胜彪
Owner NORTHEAST NORMAL UNIVERSITY
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