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2-phosphonyl quinoxaline compound and preparation method thereof

A technology for phosphonoquinoxalines and compounds, which is applied in the field of 2-phosphonoquinoxaline compounds and their preparation, achieving the effects of fast and efficient synthesis, simple operation, and mild reaction conditions

Active Publication Date: 2018-09-28
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, 2- Phosphonoquinoxaline compounds, but the above reaction requires pre-preparation of the ring system, only a single C-P bond can be constructed

Method used

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  • 2-phosphonyl quinoxaline compound and preparation method thereof
  • 2-phosphonyl quinoxaline compound and preparation method thereof
  • 2-phosphonyl quinoxaline compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation method of 2-phosphonoquinoxaline compound 1, the steps are as follows:

[0021] In a 25mL round bottom flask, dissolve 0.5mmol o-phthalonitrile in 5mL acetonitrile, then add 1.0mmol diphenylphosphine oxide and 1.0mmol silver nitrate respectively, heat to 80°C, and react for 12h. After the reaction was complete, cool to room temperature, filter off the solid residue, and spin off the solvent under reduced pressure. The obtained crude product was separated by silica gel column to obtain compound 1.

[0022] The specific results are as follows:

[0023]

[0024] 1 H NMR (400MHz, CDCl 3 )δ9.66(s,1H),8.19–8.12(m,2H),8.02–7.93(m,4H),7.87–7.77(m,2H),7.58–7.45(m,6H). 13 C NMR (101MHz, CDCl 3 )δ152.86(s), 151.62(s), 146.54(s), 146.32(s), 142.67(d, J=2.3Hz), 142.19(d, J=17.1Hz), 132.42–131.87(m), 130.94(s), 130.75(s), 130.19(d, J=1.1Hz), 129.64(d, J=1.9Hz), 128.56(d, J=12.4Hz). 31 PNMR (162MHz, CDCl 3 )δ20.35(s).

Embodiment 2

[0026] The preparation method of 2-phosphonoquinoxaline compound 2, the steps are as follows:

[0027] In a 25mL round bottom flask, dissolve 0.5mmol 3,4-dimethyl-phthalonitrile in 5mL acetonitrile, then add 1.0mmol diphenylphosphine oxide and 1.0mmol silver nitrate, and heat to 80°C , Reaction 12h. After the reaction was complete, cool to room temperature, filter off the solid residue, and spin off the solvent under reduced pressure. The obtained crude product was separated by silica gel column to obtain compound 2.

[0028] The specific results are as follows:

[0029]

[0030] 1 H NMR (400MHz, CDCl 3 )δ9.53(s,1H),8.00–7.90(m,4H),7.88(s,2H),7.55–7.43(m,6H),2.48(d,J=9.6Hz,6H). 13 C NMR (101MHz, CDCl 3 )δ151.32(s), 150.07(s), 145.78(s), 145.55(s), 143.16(s), 141.85–141.52(m), 141.30(d, J=17.3Hz), 132.29–132.05(m ), 131.25(s), 129.00(d, J=0.9Hz), 128.64–128.32(m), 20.60(s), 20.33(s). 31 P NMR (162MHz, CDCl 3 )δ20.49(s).

Embodiment 3

[0032] The preparation method of 2-phosphonoquinoxaline compound 3, the steps are as follows:

[0033] In a 25mL round bottom flask, dissolve 0.5mmol 3,4-dichloro-phthalonitrile in 5mL acetonitrile, then add 1.0mmol diphenylphosphine oxide and 1.0mmol silver nitrate respectively, heat to 80°C, Reaction 12h. After the reaction was complete, cool to room temperature, filter off the solid residue, and spin off the solvent under reduced pressure. The obtained crude product was separated by silica gel column to obtain compound 3.

[0034] The specific results are as follows:

[0035]

[0036] 1 H NMR (400MHz, CDCl 3 )δ9.65(s,1H),8.31(d,J=2.5Hz,2H),8.00–7.89(m,4H),7.62–7.48(m,6H). 13 C NMR (101MHz, CDCl 3 )δ154.39(s), 153.18(s), 147.40(d, J=21.6Hz), 141.37(d, J=2.3Hz), 140.72(d, J=17.3Hz), 136.88(s), 135.76( s), 132.53(d, J=2.8Hz), 132.09(d, J=9.7Hz), 131.46(s), 130.74–130.14(m), 128.67(d, J=12.4Hz). 31 PNMR (162MHz, CDCl 3 )δ20.50(s).

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Abstract

The invention discloses a 2-phosphonyl quinoxaline compound and a preparation method thereof. Silver nitrate used as a catalyst, o-xylene dicyanide, phosphorus diphenyl oxide or H-phosphite ester usedas a starting material, and acetonitrile used as a solvent react with one another at 80 DEG C for 12 h, thus obtaining a target product. The invention firstly provides a novel method for preparing the 2-phosphonyl quinoxaline compound through series cyclization of o-xylene dicyanide used as a free radical acceptor. Compared with a conventional method, the method disclosed by the invention has theadvantages that a quinoxaline ring system is not required to be prepared in advance, a 'one-pot procedure' is implemented, and a ring system and a C-P key are constructed at the same time; the methodhas the advantages of mild reaction condition, simple operation and the like; a 2-phosphonyl quinoxaline small-molecular library can be quickly and efficiently synthesized; the 2-phosphonyl quinoxaline compound and the preparation method thereof have a wide application prospect in the field of pharmaceutical and chemical industries.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a 2-phosphonoquinoxaline compound and a preparation method thereof. Background technique [0002] Organophosphorus compounds, especially heterocyclic organophosphorus compounds, have broad applications in the fields of organic synthesis, materials chemistry, and medicinal chemistry. After some heterocyclic compounds are attached with phosphorus-containing groups, they can enhance biological responses, improve drug efficacy or improve material properties. Quinoxalines are an extremely important class of heterocyclic core structures, which widely exist in natural products and drug molecules. In recent years, 2- Phosphonoquinoxaline compounds, but the above reaction requires the pre-preparation of the ring system, and only a single C-P bond can be constructed. [0003] The present invention provides for the first time a new method for preparing 2-phosphonoquinoxaline com...

Claims

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Application Information

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IPC IPC(8): C07F9/6509
CPCC07F9/650994
Inventor 陈晓岚刘琰於兵屈凌波孙远强
Owner ZHENGZHOU UNIV