Novel selenization method for imidazopyridine derivative C3 position

A technology of imidazopyridine and its derivatives, which is applied in the fields of organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve the problems of insufficient range of substrates, insufficient range of reaction types, high reaction temperature, etc., and achieve good compatibility, The steps are simple and easy to operate, and the effect of high yield

Inactive Publication Date: 2018-06-22
ANYANG NORMAL UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Previously, the selenization reaction of imidazopyridine compounds required metered proton acid or metal salt as a catalyst. At the same time, this method also faced the problem that the scope of substrates was not wide enough. The substrates needed to be prepared in advance, and the selenium source was limited to alkyl amination. Reagent Limitations
With the rapid development of the C-H bond functionalization strategy in recent years, the C3 regioselective functionalization reaction of imidazopyridine compounds has developed rapidly, but this type of reaction also suffers from insufficient reaction types, high reaction temperature, and low yield. Limiting factors (C. Ravi, D.C. Mohan, S. Adimurthy, Org. Lett., 2014, 16, 2978)

Method used

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  • Novel selenization method for imidazopyridine derivative C3 position
  • Novel selenization method for imidazopyridine derivative C3 position
  • Novel selenization method for imidazopyridine derivative C3 position

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 50mL round bottom flask, add 0.1941g imidazopyridine, 0.3139g diphenyl diselenide, 0.2358g elemental iodine, 0.2120g potassium carbonate, 6.0mL dichloroethane (DCE), heat at 85°C, and react for 6h to The imidazopyridine reaction was complete (monitored by thin layer chromatography TLC). The reaction mixture was poured into 20 mL of water and extracted with ethyl acetate (10 mL×5). The organic phases were combined and dried with anhydrous sodium sulfate; after the solvent was evaporated, the residue was separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 6 / 1) to obtain a white solid imidazopyridine derivative at position C3 The selenization product was 0.3083g, and the yield was 88%.

[0030] The specific response is shown in the following formula:

[0031]

[0032] The 1H NMR spectrum of the selenization product at the C3 position of the imidazopyridine derivative is as follows figure 1 As shown, the spectrogram analysis data is as f...

Embodiment 2

[0035] In a 50mL round bottom flask, add 0.2280g 3-chlorophenylimidazopyridine, 0.3139g diphenyl diselenide, 0.2358g elemental iodine, 0.2120g potassium carbonate, 6.0mL dichloroethane (DCE), heat 85 At °C, the reaction was conducted for 6 hours until the imidazopyridine reaction was completed (monitored by thin layer chromatography TLC). The reaction mixture was poured into 20 mL of water, extracted with ethyl acetate (10 mL×5), and the organic phases were combined and dried with anhydrous sodium sulfate; after the solvent was evaporated, the residue was separated by silica gel column chromatography (eluent: petroleum ether / Ethyl acetate=6 / 1) to obtain 0.3456 g of the selenization product at the C3 position of the white solid imidazopyridine derivative, with a yield of 90%.

[0036] The specific response is shown in the following formula:

[0037]

[0038] The 1H NMR spectrum of the selenization product at the C3 position of the imidazopyridine derivative is as follows figure 2...

Embodiment 3

[0041] In a 50mL round bottom flask, add 0.2121g 4-fluorophenylimidazopyridine, 0.3139g diphenyl diselenide, 0.2358g elemental iodine, 0.2120g potassium carbonate, 6.0mL dichloroethane (DCE), heat 85 ℃, react for 6 hours until the imidazopyridine reaction is complete (TLC monitoring by thin layer chromatography); pour the reaction mixture into 20 mL of water, extract with ethyl acetate (10 mL×5), combine the organic phases, and dry with anhydrous sodium sulfate; After removing the solvent, the residue was separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=6 / 1) to obtain 0.2981 g of the selenization product at the C3 position of the imidazopyridine derivative as a white solid, with a yield of 81%.

[0042] The specific response is shown in the following formula:

[0043]

[0044] The 1H NMR spectrum of the selenization product at the C3 position of the imidazopyridine derivative is as follows image 3 As shown, the spectrogram analysis data is as fo...

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Abstract

The invention discloses a novel selenization method for an imidazopyridine derivative C3 position under the condition of elementary substance iodine catalysis, and belongs to the technical field of organic synthesis. The novel selenization method adopts elementary substance iodine as a catalyst to construct a catalytic system, and greatly expands selection of a selenium reagent in the selenizationreaction of a pyridine compound C3 position; catalysis of noble metal salt and assistance of protonic acid are not needed, the selenization reaction of the imidazopyridine derivative C3 position canbe smoothly realized under the condition of the elementary substance iodine catalysis. The novel selenization method has the characteristics that the raw material is easy to obtain, the steps are simple and easy to operate, the functional group compatibility is good, the yield is high, and the like, the novel selenization method is suitable for the selenization reaction at a C3 position of synthesizing various imidazopyridine derivatives and suitable for large-scale industrial production.

Description

Technical field [0001] The invention belongs to the technical field of organic synthetic chemistry, and particularly relates to a new method for the C3 selenization reaction of imidazopyridine derivatives and various selenization reagents under the condition of elemental iodine catalysis. Background technique [0002] Imidazopyridine compounds are an important class of nitrogen-containing fused heterocyclic compounds, which have a wide range of applications in the fields of medicine, pesticides, and materials. In addition, this type of compound is easier to carry out structural modification and can better introduce various functional groups. [0003] In recent years, organic selenium reagents have aroused the interest of many chemists in synthetic application research. Organic selenium reagents can not only be used as oxidants and reducing agents. Since the σ bonds formed by organic selenium compounds are weaker than those formed by sulfides, they are more likely to break. Therefo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07B47/00
CPCC07B47/00C07D471/04
Inventor 孙凯王薪刘林
Owner ANYANG NORMAL UNIV
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