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A kind of preparation method of 2,4-disubstituted pyrrole derivatives

A technology for disubstituted pyrroles and derivatives, applied in 2 fields, can solve the problems of low universality, numerous and complicated operation steps, etc., and achieve the effects of strong reaction specificity, wide substrate range and short reaction time.

Active Publication Date: 2021-02-02
HUAQIAO UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these reactions have complex substrates, many operating steps, and low universality.

Method used

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  • A kind of preparation method of 2,4-disubstituted pyrrole derivatives
  • A kind of preparation method of 2,4-disubstituted pyrrole derivatives
  • A kind of preparation method of 2,4-disubstituted pyrrole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of 2,4-diphenylpyrrole

[0022]

[0023] Add (Z)-1,3-diphenyl-3-(N-propargylamino)prop-2-en-1-one 0.5mmol, potassium carbonate 0.6mmol, N,N-dimethylacetamide 5mL In a 10mL reaction tube, place in an oil bath at 140°C and react for 24h. 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 column chromatography to obtain 99.1 mg of the target product with a yield of 90%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, DMSO) δ11.44(s, 1H), 7.69(d, J=7.8Hz, 2H), 7.62(d, J=7.7Hz, 2H), 7.35(m, 5H), 7.15(m , 2H), 6.96(s, 1H); 13 C NMR (100 MHz, DMSO) δ 136.2, 133.1, 132.7, 129.1, 129.0, 126.1, 125.5, 125.2, 124.9, 123.9, 117.0, 103.6.

Embodiment 2

[0025] Preparation of 2-phenyl-4-(p-tolyl)pyrrole

[0026]

[0027] (Z)-1-(p-tolyl)-3-phenyl-3-(N-propargylamino)prop-2-en-1-one 0.5mmol, potassium carbonate 0.6mmol, N,N-dimethyl Add 5mL of acetamide into a 10mL reaction tube, place in an oil bath at 140°C, and react for 24h. 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 column chromatography to obtain 108.3 mg of the target product with a yield of 93%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )68.40(s, 1H), 7.48(dd, J=17.2, 7.9Hz, 4H), 7.38(t, J=7.6Hz, 2H), 7.22(d, J=7.4Hz, 1H), 7.17(d, J=7.8Hz, 2H), 7.10(s, 1H), 6.80(s, 1H), 2.36(s, 3H); 13 C NMR (100MHz, CDCl 3 ) δ 135.2, 132.9, 132.5, 129.3, 128.9, 126.6, 126.4, 125.1, 123.8, 115.2, 103.9, 21.0.

Embodiment 3～13

[0029] The operation steps are the same as in Example 2, the difference is: according to the following reaction formula, the substituent R of enaminone is changed 1 and R 2 , to obtain different 2,4-disubstituted pyrrole derivatives.

[0030]

[0031] The reaction temperature in this example is 140°C.

[0032] The structural characterization data of some products are as follows:

[0033] Characterization data for product 2a: 1 H NMR (400MHz, CDCl 3 )δ8.44(s, 1H), 7.50(d, J=7.8Hz, 2H), 7.38(t, J=7.6Hz, 2H), 7.30-7.20(m, 2H), 7.17(d, J=7.6 Hz, 1H), 7.11(s, 2H), 6.84-6.72(m, 2H), 3.85(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ159.9, 136.9, 133.0, 132.4, 129.6, 128.9, 126.5, 123.8, 117.8, 115.7, 111.1, 110.9, 104.0, 55.2; HRMS (ESI) calcd for C 17 h 16 NO[M+H]+250.1226, found: 250.1232.

[0034] Characterization data for product 2b: 1 H NMR (400MHz, DMSO) δ11.44(s, 1H), 7.69(d, J=7.9Hz, 2H), 7.64(dd, J=7.5, 5.7Hz, 2H), 7.38(t, J=7.4Hz , 2H), 7.32(s, 1H), 7.22-7.12(m, 3H), 6...

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Abstract

The invention discloses a preparation method of a 2,4-di-substituted pyrrole derivative. The reaction equation is shown in the description. By adopting the method, a pyrrole derivative with a plurality of substituents which is difficult to obtain with other methods can be synthesized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2,4-disubstituted pyrrole derivatives. Background technique [0002] Pyrrole derivatives ubiquitously exist in various natural products and drug molecules, and have a wide range of biological activities, [0003] It has important application value in anti-diabetes (US Patent: 4282242, 1981), anti-fungal (Japanese Patent: 8179672, 1981), and anti-bacteria (Japanese Patent: 6814699, 1968). Therefore, the research on new synthetic methods of pyrrole compounds and their analogs has important application value and has attracted the attention of researchers in related fields. The synthesis of traditional pyrrole compounds mainly includes Paal-Knorr method and Hantzsch method. Most of these reactions have complex substrates, numerous operating steps, and low universality. Contents of the invention [0004] The purpose of the present inv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/323C07D207/33C07D207/333C07D409/04
CPCC07D207/323C07D207/33C07D207/333C07D409/04
Inventor 程国林薛露露
Owner HUAQIAO UNIVERSITY
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