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Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis

A technology for the preparation of formylphenyl and catalysis, which is applied in chemical instruments and methods, the preparation of organic compounds, and the preparation of carboxylic acid amides. It can solve the problems of poor selectivity, failure to obtain the target product, and complexity, and achieve low cost. , simple post-processing, high reaction efficiency

Active Publication Date: 2016-09-21
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the photocatalytic reaction in which oxygen participates, due to the simultaneous existence of energy transfer pathways (generating singlet oxygen) and single electron transfer pathways (generating superoxide negative ions) during the reaction process, the selectivity of the reaction product is often poor and the product is complicated or even taken. less than the target product, which prevents the application of this type of reaction
Therefore, improving the selectivity of aerobic oxidation reactions is challenging but significant.

Method used

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  • Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis
  • Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis
  • Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] The structural formula of compound 2a is as follows:

[0022]

[0023] The synthetic route of compound 2a is as follows:

[0024]

[0025] The synthetic steps of compound 2a are as follows:

[0026] (1) Add 28 μL (0.0005 mmol, 0.005 equiv) of DPZ solution (1 mg dissolved in 160 μl acetonitrile) into a 10 mL reaction flask, and then remove the solvent by rotary evaporation;

[0027] (2) Then add magneton, N-methylindole 1a (0.1mmol, 1.0equiv), solvent (2.0mL, CH 3 CN:H 2 O volume ratio=10:1), K 3 PO 4 (0.3mmol, 3equiv.) and 10equiv% TEMPO (0.01mmol) as additives, seal the reaction bottle, and insert an oxygen bulb on the bottle stopper to provide oxygen to the reaction bottle;

[0028] (3) Put the reaction bottle into a 25°C incubator, and stir the reaction at a distance of 5cm from a 3W blue light (λ=450-455nm); (4) The reaction is detected by a TLC plate. After the reaction is complete, extract with ethyl acetate , spin-dried, passed through the column (col...

Embodiment 2

[0031]

[0032] Product Name: N-(2-Formylphenyl)-N-Benzylformamide

[0033] In step (2), N-methylindole 1a was replaced with p-N-benzylindole 1b, and other preparation steps and purification methods were carried out with reference to Example 1; yellow oil, 96% yield. 1 H NMR (300MHz, CDCl 3 )δ9.77 (s, 1H), 8.64 and 8.27 (s, 1H, CHO rotameric), 7.92–7.87 (m, 1H), 7.64–7.55 (m, 1H), 7.43–7.51 (m, J=11.3, 7.5,1H), 7.31–7.28(m,1H), 7.25–7.03(m,5H), 4.98 and 4.83(s,2H,CH 2 rotameric). 13 C NMR (75MHz, CDCl 3 )δ189.2, 189.0, 162.8, 162.3, 142.0, 139.9, 135.3, 135.2, 134.9, 132.8, 132.3, 130.4, 129.2, 129.1, 129.0, 128.8, 128.6, 128.6, 128.5, 128.2 HR, 58.2 m / z 240.1032(M+H + ), calc.for C 15 h 14 NO 2 240.1025.

Embodiment 3

[0035]

[0036] Product name: N-(2-formylphenyl)-N-phenylcarboxamide

[0037] In step (2), p-N-phenylindole 1 was used to replace N-methylindole 1a, and other preparation steps and purification methods were carried out with reference to Example 1; yellow oil, 85% yield. 1HNMR (300MHz, CDCl3) δ10.14 and 10.07 (s, 1H, CHOrotameric), 8.84 and 8.54 (s, 1H, CHO rotameric), 8.01 (dd, J = 7.7, 1.6, 1H), 7.73-7.65 (m, 1H),7.60–7.48(m,1H),7.43–7.27(m,4H),7.25–7.13(m,2H).13C NMR(75MHz,CDCl3)δ189.0,188.9,162.3,161.6,141.6,140.4,135.4 ,135.1,132.2,130.6,130.2,129.9,129.7,129.3,128.9,128.7,126.9,126.6,124.5,123.4.HRMS(ESI)m / z 226.0873(M+H + ), calc.for C 14 h 12 NO 2 226.0868.

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Abstract

The invention relates to a method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis, belonging to the technical field of visible light catalytic synthesis. A synthetic route is described in the description, wherein the structural formula of DPZ is described in the description, R<1> is -H, -OMe, -F or -Cl, and R<2> is -Me, -Bn or -Ph; the synthetic process comprises the steps of dissolving a compound 1, the DPZ, K3PO4 and TEMPO into a mixed solvent of CH3CN and water, carrying out a reaction at the constant temperature of 25 DEG C under a blue lamp light source in an oxygen atmosphere, tracking and monitoring by using thin layer chromatography (TLC), and after the reaction is finished, carrying out column chromatographic separation to obtain a compound 2. The method can be used for efficiently preparing the N-(2-formyl phenyl) N-substituted formamide derivatives, and has the advantages of being environmental-friendly, high in reaction efficiency, simple in aftertreatment and low in cost.

Description

technical field [0001] The invention belongs to the technical field of visible light catalytic synthesis, and in particular relates to a method for preparing N-(2-formylphenyl) N-substituted formamide derivatives by visible light catalysis. Background technique [0002] N-methylformamide compound is an important raw material for organic synthesis, and it is also a key intermediate for the synthesis of many biologically active compounds. Production of pharmaceuticals, synthetic leather, artificial leather, etc. [0003] N-phenyl-N-substituted carboxamides are key steps in the synthesis of many natural products and drugs. N-(2-formylphenyl)-N-methylformamide is hydrolyzed under the action of NaOH to generate 2-methylaminobenzaldehyde, and 2-methylaminobenzaldehyde reacts with indole to obtain a new antimalarial drug Phyllophylline. N-(2-formylphenyl)-N-methylformamide generates amino-protected alcohol compounds through hydrolysis and reduction process, and removes benzyl gr...

Claims

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Application Information

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IPC IPC(8): C07C231/10C07C233/33C07D471/04
CPCC07C231/10C07D471/04C07C233/33
Inventor 江智勇朱博赵筱薇李江涛张宸浩
Owner HENAN UNIVERSITY
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