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Synthesis method of pyran[2,3-b]pyridine derivatives

A synthesis method, 3-b technology, applied in organic chemistry and other directions, can solve problems such as complex reaction process

Inactive Publication Date: 2014-06-11
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above synthesis method uses a special reaction device, and the reaction process is complicated
And by aldehyde, 2,4-dihydroxypyridine and malononitrile and its derivatives in absolute ethanol as raw materials, ammonium acetate is used as a catalyst to synthesize 2-amino-4-phenyl-5-oxo-5 in one step, The method of 8-dihydroxy-4-H-pyrano[2,3-b]pyridine-3-carbonitrile derivatives has not been reported yet

Method used

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  • Synthesis method of pyran[2,3-b]pyridine derivatives
  • Synthesis method of pyran[2,3-b]pyridine derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0008] Preparation of 2-amino-4-(2-chlorophenyl)-5-oxo-5,8-dihydroxy-4-H-pyrano[2,3-b]pyridine-3-carbonitrile: in 5 In milliliter of absolute ethanol, add 1 mmol of 2-chlorobenzaldehyde (0.14g), 1 mmol of 2,4-dihydroxypyridine (0.11g) and 1 mmol of malononitrile (0.066g), at reflux Under the condition of reaction for 30min, TLC tracking and monitoring, after the reaction was completed, directly cooled to obtain the corresponding product 2-amino-4-phenyl-5-oxo-5,8-dihydroxy-4-H-pyrano[ 2,3-b]pyridine-3-carbonitrile (0.23 g, 82% yield). This product is white powder, mp: 276-278℃.

Embodiment 2

[0010] Preparation of 2-amino-4-(3-chlorophenyl)-5-oxo-5,8-dihydroxy-4-H-pyrano[2,3-b]pyridine-3-carbonitrile: in 5 Add 1 mmol of 3-chlorobenzaldehyde (0.14g) in milliliter of absolute ethanol, 1 mmol of 2,4-dihydroxypyridine (0.11g) and 1 mmol of malononitrile (0.066g), at reflux Under the condition of reaction for 20min, TLC tracking and monitoring, after the reaction was completed, directly cooled to obtain the corresponding product 2-amino-4-phenyl-5-oxo-5,8-dihydroxy-4-H-pyrano[ 2,3-b]pyridine-3-carbonitrile (0.22 g, 80% yield). This product is white powder, mp: 254-256℃.

Embodiment 3

[0012] Preparation of 2-amino-4-(4-chlorophenyl)-5-oxo-5,8-dihydroxy-4-H-pyrano[2,3-b]pyridine-3-carbonitrile: in 5 Add 1 mmol of 4-chlorobenzaldehyde (0.14g) in milliliter of dehydrated alcohol, 1 mmol of 2,4-dihydroxypyridine (0.11g) and 1 mmol of malononitrile (0.066g), at reflux Under the condition of reaction for 30min, TLC tracking and monitoring, after the reaction was completed, directly cooled to obtain the corresponding product 2-amino-4-phenyl-5-oxo-5,8-dihydroxy-4-H-pyrano[ 2,3-b]pyridine-3-carbonitrile (0.24 g, 83% yield). This product is white powder, mp: 263-265℃.

[0013] The reaction raw materials, reaction conditions and productive rate of embodiment 1-20 are shown in Table 1.

[0014] The reaction raw material of table 1 embodiment 1-20, reaction condition and productive rate

[0015]

[0016] As can be seen from Table 1, the method raw material of the present invention is easy to get, simple and safe to operate, mild reaction conditions, high yield, s...

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Abstract

The invention relates to the synthesis of pyran[2,3-b]pyridine derivatives, and specifically relates to the synthesis of 2-amino-4-phenyl-5-oxo-5,8-dihydroxyl-4-H-pyran[2,3-b]-3-nitrile, which is prepared by taking aldehyde, 2,4-dihydroxylpyridine, and malononitrile as the raw materials, and then subjecting the three components to an one-step reaction. The synthesis method has the advantages of simple synthesis technology route and mild reaction conditions, and the total yield of the synthesis method can reach 70% or more.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the production of 2-amino-4-phenyl-5-oxo-5,8-dihydroxy-4-H-pyrano[2,3-b]pyridine-3-carbonitrile resolve resolution. Background technique [0002] Pyrano[2,3-b]pyridine is a class of heterocyclic compounds with important physiological and pharmacological activities. It has antimicrobial, anti-inflammatory, antibacterial and other activities. Therefore, pyranopyridine derivatives have always been a focus of attention of chemists and pharmaceutical scientists. It has been reported in the literature that 2-methoxypyridine is used as a raw material to synthesize pyrano[2,3-b]pyridine derivatives with 1,4-naphthoquinone structure (H.J.Finlay et al. / Bioorg.Med.Chem.Lett .18(2008) 2714-2718), or 6-(2-chloro-phenyl)-5-(4-chloro-phenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile as The raw material, THF as the solvent, synthesized this type of compound at room temperature (C.B.Ma...

Claims

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Application Information

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IPC IPC(8): C07D491/052
CPCC07D491/052
Inventor 李玉玲王凯杜百祥
Owner XUZHOU NORMAL UNIVERSITY
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