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Multi-substituted pyridine derivatives and preparation method thereof

A derivative and multi-substitution technology, applied in the field of multi-substituted pyridine derivatives and their preparation, can solve the problems of difficult synthesis of multi-substituted pyridine derivatives, difficult preparation of raw materials, metal residues, etc., and achieve strong reaction specificity and post-production Dealing with green, short reaction time effects

Active Publication Date: 2018-01-09
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these methods all have many problems: 1) with 1,5-dicarbonyl compound as raw material, raw material is not easy to prepare, and some 1,5-dicarbonyl compound is difficult to obtain; 2) reaction needs to use expensive transition metal catalyst, easy Causes metal residues in the product, which is limited in use in the pharmaceutical industry; 3) It is difficult to synthesize polysubstituted pyridine derivatives, especially highly selective synthesis of polysubstituted asymmetric polysubstituted pyridine derivatives

Method used

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  • Multi-substituted pyridine derivatives and preparation method thereof
  • Multi-substituted pyridine derivatives and preparation method thereof
  • Multi-substituted pyridine derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of 2,4,6-triphenylpyridine

[0022]

[0023] Add 0.5mmol of 1,3-diphenyl-prop-2-yn-1-one, 0.5mmol of 1-phenylethylamine, 1mmol of potassium hydroxide, and 1.5mL of dimethyl sulfoxide into a 10mL reaction tube, and place In an oil bath at 100°C, react for 12h. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by silica gel column chromatography to obtain 106.7 mg of the target product with a yield of 69%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.24–8.17(m,4H),7.87(s,2H),7.76–7.71(m,2H),7.53–7.40(m,9H); 13 C NMR (100MHz, CDCl 3 )δ157.5, 150.16(s), 139.6, 139.0 129.1, 129.0, 128.9, 128.7, 127.2, 127.1, 117.1.

Embodiment 2

[0025] Preparation of 2,6-diphenyl-4-(4-methylphenyl)pyridine

[0026]

[0027] Add 0.5mmol of 3-phenyl-1-(4-methylphenyl)-prop-2-yn-1-one, 0.5mmol of 1-phenylethylamine, 1mmol of potassium tert-butoxide, and 5mL of dimethyl sulfoxide into 10mL of In a reaction tube, place it in an oil bath at 80°C and react for 20 hours. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by silica gel column chromatography to obtain 125.2 mg of the target product with a yield of 78%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.19(d, J=7.5Hz, 4H), 7.85(s, 2H), 7.62(d, J=8.0Hz, 2H), 7.50(t, J=7.5Hz, 4H), 7.43(d, J=7.3Hz, 2H), 7.30(d, J=7.9Hz, 2H), 2.41(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ157.4, 150.0, 139.6, 139.0, 136.0, 129.8, 128.9, 128.6, 127.1, 126.9, 116.8, 21.2. ...

Embodiment 3

[0029] Preparation of 2,6-diphenyl-4-(2-tolyl)pyridine

[0030]

[0031] Add 0.5mmol of 3-phenyl-1-(2-methylphenyl)-prop-2-yn-1-one, 0.5mmol of 1-phenylethylamine, 1mmol of potassium tert-butoxide, and 3mL of dimethyl sulfoxide into 10mL of In a reaction tube, place it in an oil bath at 120° C., and react for 12 hours. Stop the reaction and cool to room temperature. The reaction solution was diluted with ethyl acetate, washed three times with water, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, filter, concentrate, and purify by silica gel column chromatography to obtain 115.6 mg of the target product with a yield of 72%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.18(d, J=7.3Hz, 4H), 7.66(s, 2H), 7.49(t, J=7.5Hz, 4H), 7.42(t, J=7.2Hz, 2H), 7.32(d, J=5.3Hz, 4H), 2.35(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ156.8, 151.3, 139.8, 139.5, 135.1, 130.7, 129.2, 129.0, 128.7, 128.3, 127.1, 126.1, 119.3, 20.4.

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Abstract

The invention discloses a polysubstituted pyridine derivative and a preparation method thereof. The derivative has a structure as shown in specification, wherein R1, R2, R3, R4 and R5 all are any one selected from hydrogen atom, halogen atom, alkyl, aryl, substituted aryl, acyl, amino, nitryl and alkoxy; the invention also discloses a preparation method of the polysubstituted pyridine derivative; the preparation method comprises the following steps: by taking acetyenic ketone and 1-arylethylamine as raw materials, and under the action of appropriate alkali, heating to have a reaction in the solvent to obtain the polysubstituted pyridine derivative as shown in the formula at high yield. The preparation method is mild in reaction condition, short in reaction time, wide in substrate range, high in reaction specifity, high in yield and simple in after-treatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to multi-substituted pyridine derivatives and a preparation method thereof. Background technique [0002] Multi-substituted pyridine derivatives are a class of organic synthesis intermediates with a wide range of uses, and have important application values ​​in natural products, pharmaceutical production, organic synthesis, and material science. Therefore, the research on new synthesis methods of multi-substituted pyridines has important application value and has attracted the attention of researchers in related fields. [0003] The traditional methods for synthesizing pyridine derivatives include the condensation reaction of amine compounds and 1,5-dicarbonyl compounds, and transition metal-catalyzed cyclization coupling reactions. But these methods all have many problems: 1) with 1,5-dicarbonyl compound as raw material, raw material is not easy to prepare, and some 1,5-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/16C07D213/30C07D213/26C07D409/04
CPCC07D213/16C07D213/26C07D213/30C07D409/04
Inventor 崔秀灵沈金海
Owner HUAQIAO UNIVERSITY
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