Method for synthesizing indolizine compound under catalysis of silver

A compound, the technology of indolizine, which is applied in the field of silver-catalyzed synthesis of indolizine compounds, can solve the problems of inconvenient operation, high temperature and high pressure, and low yield, and achieve the effects of simple operation, mild reaction conditions, and easy separation and purification

Active Publication Date: 2021-08-03
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these synthetic methods have certain defects, such as the need for high temperature and high pressure, a large amount of alkali and equivalent or even excess oxidant, inconvenient operation, low yield, etc.

Method used

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  • Method for synthesizing indolizine compound under catalysis of silver
  • Method for synthesizing indolizine compound under catalysis of silver
  • Method for synthesizing indolizine compound under catalysis of silver

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of indolizine derivative 3a

[0034]

[0035] Add N-phenacylmethylpyridine bromide 1a (0.139 g, 0.5 mmol), silver carbonate (0.207 g, 0.75 mmol), triethylamine (104 μL, 0.75 mmol) into a 10 mL pressure-resistant tube with a magnetic stirring device , 1,4-dioxane (3 mL) and ethyl isocyanacetate 2a (66 μL, 0.6 mmol), stirred at 20° C. for 2 h. TLC (developing agent is V 石油醚 :V 乙酸乙酯 =10:1) The detection substrate disappears, and the reaction ends. The reaction solution was poured into a round-bottomed flask, and after distillation under reduced pressure, it was subjected to silica gel column chromatography (eluent was V 石油醚 :V 乙酸乙酯 =15:1) separation, the resulting eluate was distilled under reduced pressure and dried to obtain a white solid, which was confirmed to be indolizine derivative 3a by NMR and MS, with a yield of 88%.

[0036] Through hydrogen spectrum, carbon spectrum and high-resolution mass spectrometry detection of indoliz...

Embodiment 2

[0039] Indolizine derivative 3b was prepared by replacing 1a in Example 1 with 1b.

[0040]

[0041] Add N-phenacylmethylpyridine bromide 1b (0.148g, 0.5mmol), silver carbonate (0.276g, 1.0mmol), potassium carbonate (0.104g, 0.75mmol) into a 10mL pressure-resistant tube with a magnetic stirring device , 1,4-dioxane (3 mL) and ethyl isocyanacetate 2a (66 μL, 0.6 mmol), stirred at 20° C. for 2 h. TLC (developing agent is V 石油醚 :V 乙酸乙酯 =10:1) The detection substrate disappears, and the reaction ends. The reaction solution was poured into a round-bottomed flask, and after distillation under reduced pressure, it was subjected to silica gel column chromatography (eluent was V 石油醚 :V 乙酸乙酯 =15:1) separation, the resulting eluate was distilled under reduced pressure and dried to obtain a white solid, which was confirmed to be indolizine derivative 3b by NMR and MS, with a yield of 86%.

[0042]Through the hydrogen spectrum, carbon spectrum and high-resolution mass spectrum dete...

Embodiment 3

[0045] Indolizine derivative 3c was prepared by substituting 1c for 1a in Example 1.

[0046]

[0047] Add N-phenacylmethylpyridine bromide 1c (0.156 g, 0.5 mmol), silver carbonate (0.207 g, 0.75 mmol), triethylamine (104 μL, 0.75 mmol) into a 10 mL pressure-resistant tube with a magnetic stirring device , 1,2-dichloroethane (2 mL) and ethyl isocyanacetate 2a (66 μL, 0.6 mmol), stirred at 20° C. for 2 h. TLC (developing agent is V 石油醚 :V 乙酸乙酯 =10:1) The detection substrate disappears, and the reaction ends. The reaction solution was poured into a round-bottomed flask, and after distillation under reduced pressure, it was subjected to silica gel column chromatography (eluent was V 石油醚 :V 乙酸乙酯 =15:1) separation, the resulting eluate was distilled under reduced pressure and dried to obtain a white solid, which was confirmed to be indolizine derivative 3c by NMR and MS, with a yield of 91%.

[0048] Through the hydrogen spectrum, carbon spectrum and high-resolution mass sp...

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PUM

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Abstract

The invention discloses a method for synthesizing indolizine compounds under the catalysis of silver, which comprises the following steps of in an organic solvent system, stirring N-benzoylmethyl pyridinium bromide as shown in a formula (1) and an isocyanide compound as shown in a formula (2) according to a feeding molar ratio of 1: (1.2-2.0) in the presence of a metal silver salt as a catalyst to react in the air under an alkaline condition, and carrying out TLC tracking detection until the reaction is complete, and carrying out post-treatment on the reaction liquid to obtain the indolizine compound as shown in a formula (3). The method is easy to operate, raw materials and reagents are easy to obtain, reaction conditions are mild, a reaction system is environmentally friendly, products are easy to separate and purify, the yield reaches up to 91%, and the method is suitable for efficient and high-yield preparation of indolizine compounds and particularly suitable for synthesis of various 1, 2-substituted indolizine compounds. The method is suitable for large-scale industrial production, and has wide application prospects and important significance in organic synthesis.

Description

technical field [0001] The invention belongs to the technical field of fine chemical organic synthesis, and in particular relates to a silver-catalyzed method for synthesizing indolizine compounds. Background technique [0002] Indolizine, also known as indolizine, is isomers with indole and isoindole. It is a common class of nitrogen-fused heterocyclic compounds with 10π electron system. An important structural unit of a molecule. Because of its unique biological and pharmacological activities such as antiviral, antibacterial, anti-inflammatory, antihypertensive, and antitumor, indolizine derivatives have been widely used in the fields of medicine, pesticides, and biology. For example, swainsonine can inhibit α-mannosidase II in the Golgi complex, thereby inhibiting the synthesis of N-linked oligosaccharides in malignant tumor cells. Lamellarin is a pyrrole alkaloid series compound with strong physiological activity and complex structure isolated from marine molluscs. It ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/584
Inventor 王亦纯陈艳刘晓艺刘建全
Owner XUZHOU NORMAL UNIVERSITY
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