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A method for synthesizing 1-halogen-2-aryl indolizine compounds

A compound, the technology of pyrazine, which is applied in the field of organic and pharmaceutical synthesis, can solve the problems of few suitable substrates, many synthesis steps, and difficult synthesis, and achieve the effects of mild reaction conditions, high reaction efficiency, and wide substrate range

Inactive Publication Date: 2011-12-28
TONGJI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the method has a high yield, it is difficult to synthesize raw materials
[0009] The above-mentioned methods for synthesizing indolizine compounds all have shortcomings such as many synthetic steps, low yield, few suitable substrates, expensive raw materials or difficult synthesis, and some reactions need to be catalyzed by transition metal catalysts.

Method used

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  • A method for synthesizing 1-halogen-2-aryl indolizine compounds
  • A method for synthesizing 1-halogen-2-aryl indolizine compounds
  • A method for synthesizing 1-halogen-2-aryl indolizine compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of 1-bromo-2-p-nitrophenyl-3-ethoxycarbonyl indolizine

[0054]

[0055] Add 0.3mmol N-ethoxycarbonylmethylpyridinium bromide, 0.6mmol 1,1-dibromo-2-p-nitrophenylethylene, 5mL tetrahydrofuran, 1.35mmol DBU to a 25mL round bottom flask, and then the reaction solution Magnetically stirred and refluxed at 90°C for 12 hours. After the reaction was completed, cool to room temperature and evaporate the solvent under reduced pressure. The residue was subjected to column chromatography with ethyl acetate / petroleum ether=1:10 (v / v) as the eluent. The desired product can be obtained by separation and purification. The product is a yellow solid with a yield of 95%.

[0056] 1 H NMR (400MHz, CDCl 3 ): δ = 9.60(d, J = 7.2 Hz, 1H), 8.37(d, J = 8.4 Hz, 2H),7.73(d, J = 8.0 Hz, 2H), 7.53(d, J = 9.6 Hz, 1H), 7.16(t, J = 7.8 Hz, 1H), 6.93(t, J = 7.0 Hz, 1H), 4.50(q, J = 7.0, 7.2Hz, 2H), 1.50(t, J = 7.0 Hz, 3H).

Embodiment 2

[0057] Embodiment 2: Synthesis of 1-bromo-2-p-fluorophenyl-3-ethoxycarbonyl indolizine

[0058]

[0059] Add 0.3mmol N-ethoxycarbonylmethylpyridinium bromide, 0.6mmol 1,1-dibromo-2-p-fluorophenylethylene, 5mL tetrahydrofuran, 1.35mmol DBU to a 25mL round bottom flask, and then the reaction solution was Magnetic stirring and reflux reaction at 90°C for 12 hours, after the completion of the reaction, cool to room temperature, evaporate the solvent under reduced pressure, and use ethyl acetate / petroleum ether=1:10 (v / v) as the eluent for column chromatography to separate the residue The desired product can be obtained after purification. The product is a yellow-green solid with a yield of 63%.

[0060] 1 H NMR (400MHz, CDCl 3 ): δ = 9.45 (d, J = 7.2 Hz, 1H), 7.40-7.35 (m, 3H), 7.10 (t, J = 8.4Hz, 2H), 6.97(t, J = 7.8 Hz, 1H), 6.76(t, J = 7.0 Hz, 1H), 4.39(q, J = 7.2, 6.8 Hz, 2H), 1.39(t, J = 7.2 Hz, 3H).

Embodiment 3

[0061]Embodiment 3: Synthesis of 1-bromo-2-p-chlorophenyl-3-ethoxycarbonyl indolizine

[0062]

[0063] Add 0.3mmol N-ethoxycarbonylmethylpyridinium bromide, 0.6mmol 1,1-dibromo-2-p-chlorophenylethylene, 5mL tetrahydrofuran, 1.35mmol DBU to a 25mL round bottom flask, and then the reaction solution was Magnetic stirring and reflux reaction at 90°C for 12 hours, after the completion of the reaction, cool to room temperature, evaporate the solvent under reduced pressure, and use ethyl acetate / petroleum ether=1:10 (v / v) as the eluent for column chromatography to separate the residue The desired product can be obtained after purification. The product is light yellow solid with a yield of 85%.

[0064] 1 H NMR (400MHz, CDCl 3 ): δ=9.46(d, J = 7.2 Hz, 1H), 7.40-7.35(m, 5H), 6.98(t, J = 7.8 Hz, 1H), 6.77(t, J = 6.8 Hz, 1H), 4.39(q, J = 7.0, 7.2 Hz, 2H), 1.40(t, J =7.2 Hz, 3H).

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Abstract

The invention relates to a method for synthesizing a 1-halo-2-aryl indolizine compound. According to the method, the 1-halo-2-aryl indolizine compound can be conveniently and effectively synthesized by using brominated N-ethyoxyl carbonyl methyl pyridinium salt (or chlorinated N-cyan methyl pyridinium salt) and 1,1-dibromo-2-arylethylene (or 1-halo-2-arylacetylene) as substrates under the action of alkali. Compared with the existing methods, the method provided by the invention has the advantages that the range of adaptable substrates is wide, reaction conditions are mild, no catalyst is needed, and reaction efficiency is high and is simple to operate, thus the method has an important application value.

Description

technical field [0001] The invention belongs to the technical field of organic and pharmaceutical synthesis, in particular to a method for synthesizing 1-halogen-2-aryl indolizine compounds. Background technique [0002] Indolizine is a class of indole isomers with 10π electron system. Its mother nucleus is widely found in many natural product molecules with important biological activities, such as licorice (Tabersonine), strychnine (-Strychnine), vinblastine (+Vinblastine) and so on. Indolizine has a wide range of biological activities, mainly including antitumor, antibacterial, antiviral, insecticidal, anti-inflammatory, antiarrhythmic, and antihypertensive. In recent years, it has been found that compounds with indolizine as the parent nucleus have certain curative effects on mental illness, anti-inflammation, pain relief, hypoglycemia and adult respiratory diseases. Both synthetic and naturally occurring indolizine cores may have the effects of inhibiting the central n...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 匡春香杨义文金辉
Owner TONGJI UNIV
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