Alkyne-containing quinoxalin derivative and preparation method thereof

A technology for alkyne quinoxaline and derivatives, which is applied in the field of alkyne-containing quinoxaline derivatives and their preparation, achieving the effects of less environmental pollution, less side reactions, and mild reaction conditions

Inactive Publication Date: 2012-02-08
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There is no report on the synthesis of quinoxaline derivatives using terminal alkynes and o-phenylenediamine compounds as raw materials and CuX as a reaction catalyst

Method used

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  • Alkyne-containing quinoxalin derivative and preparation method thereof
  • Alkyne-containing quinoxalin derivative and preparation method thereof
  • Alkyne-containing quinoxalin derivative and preparation method thereof

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preparation example Construction

[0036] The general formula of the preparation method of alkyne-containing quinoxaline derivatives of the present invention is as follows:

[0037]

[0038] in:

[0039] R is aryl (for example: phenyl, alkylphenyl, bromophenyl, fluorophenyl, chlorophenyl, alkoxyphenyl, thienyl, pyridyl, naphthyl, etc.), alkyl (for example: hexyl , butyl, propyl, tert-butyl, etc.) or other groups (for example: trimethylsilyl, haloalkyl, etc.).

[0040] R' is hydrogen, halogen, aryl (for example: phenyl, alkylphenyl, bromophenyl, fluorophenyl, chlorophenyl, alkoxyphenyl, thienyl, pyridyl, naphthyl, etc.) or Alkyl (for example: hexyl, butyl, propyl, tert-butyl, etc.).

[0041] CuX is CuCl, CuBr or CuI.

Embodiment 1

[0043] Example 1: Preparation and structural characterization of 2-(4-ethylphenyl)-3-(2-(4-ethylphenyl)ethynyl)quinoxaline (a)

[0044] Add 1 mmol of p-ethylphenylacetylene and 5 mmol of o-phenylenediamine into the sealed tube, add 0.2 mmol of catalyst CuCl and 2 ml of solvent chlorobenzene, react for 10 hours in an oil bath at 70 ° C under magnetic stirring, filter, and the filtrate is vortexed by vacuum distillation. The solvent was removed, the residue was dissolved in 10 mL of ethyl acetate, and then washed with water (3×2 mL) and saturated brine (2 mL) successively, the organic layer was dried over anhydrous sodium sulfate, and the ethyl acetate was removed under reduced pressure, and the obtained crude product was coated with silica gel. Column chromatography, with eluent (V 石油醚 :V 乙酸乙酯=60:1), the eluent was evaporated to dryness, and the obtained yellow oil was compound a. Its hydrogen spectrum, carbon spectrum and structural formula are as follows:

[0045] 1 HNMR ...

Embodiment 2

[0048] Example 2: Preparation and structural characterization of 2-hexyl-3-(1-octynyl)quinoxaline (b)

[0049] Add 1mmol of 1-octyne and 3mmol of o-phenylenediamine into the sealed tube, add catalyst 0.3mmol CuI, react in a water bath at 90°C under magnetic stirring for 16 hours, filter, and dissolve the filtrate in 10mL of ethyl acetate and then water (3× 2 mL), washed with saturated brine (2 mL), dried over anhydrous sodium sulfate, and then removed ethyl acetate under reduced pressure. The resulting crude product was subjected to silica gel column chromatography, and the eluent (V 石油醚 :V 乙酸乙酯 =50:1), the eluent was evaporated to dryness, and the obtained brownish-red oil was compound b. Its hydrogen spectrum, carbon spectrum and structural formula are as follows:

[0050] 1 H NMR (500MHz, CDCl 3 )δ8.05-7.95(m, 2H), 7.68(m, 2H), 3.20-3.10(t, J=5.0Hz, 2H), 2.56(t, J=7.1Hz, 2H), 1.85(m, 2H ), 1.76-1.59(m, 2H), 1.56-1.41(m, 4H), 1.41-1.29(m, 8H), 0.91(t, J=5.0Hz, 3H), 0.90...

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Abstract

The invention discloses an alkyne-containing quinoxalin derivative and a preparation method thereof. The structure general formula of the alkyne-containing quinoxalin derivative is shown in the specifications, wherein R is aryl, alkyl, trimethylsilyl or halogen alkyl; and R' is hydrogen, halogen, aryl or alkyl. The preparation method comprises the following steps of: putting terminal alkyne and an o-phenylenediamine compound serving as raw materials and CuX serving as a catalyst into a sealed pipe; reacting with magnetic stirring to obtain a crude product; and performing silica gel column chromatography to obtain the alkyne-containing quinoxalin derivative. Compared with the prior art, the invention has the advantages: the raw materials of the product are cheap and readily-available, and the method is easy to operate and control and has mild reaction conditions, high efficiency and low environmental pollution.

Description

technical field [0001] The invention relates to quinoxaline derivatives, in particular to alkyne-containing quinoxaline derivatives and a preparation method thereof. Background technique [0002] Benzopyrazine, which is fused with a benzene ring, is also called quinoxaline. Its structural formula and the numbering of each atom are as follows: [0003] [0004] The classic synthesis method of quinoxaline derivatives is obtained through the condensation reaction of o-phenylenediamine and 1,2-diketone, the reaction speed is fast, and the product crystallizes well. If catechol and ethylenediamine are used as raw materials, they can also be condensed first and then dehydrogenated to obtain quinoxaline. [0005] In recent years, researchers have made some new progress in the synthesis of quinoxaline, such as: [0006] (1) Chandrasekhar S. group using PdCl 2 / CuCl 2 The catalyst system oxidizes alkyne to the corresponding 1,2-diketone compound, the intermediate is isolated a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/42C07D409/04C07F7/10
Inventor 潘英明刘培臻王恒山
Owner GUANGXI NORMAL UNIV
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