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[1,2,4]-triazol [4,3-a] pyridines compound and synthesis method thereof

A synthesis method and compound technology, applied in organic chemistry, drug combination, blood diseases, etc., can solve the problems of low stability and safety, high toxicity of transition metals, expensive oxidants, etc., and achieve the treatment of thromboembolic diseases, The effect of short reaction time and mild conditions

Inactive Publication Date: 2018-07-20
BAOJI UNIV OF ARTS & SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although there are many methods for synthesizing [1,2,4]-triazolo[4,3-a]pyridine compounds, especially for preparing triazolopyridine compounds through intermolecular interactions, there are relatively Many defects, such as the use of highly toxic transition metals, expensive oxidants, low stability and safety, complex and harsh conditions, expensive raw materials, etc.

Method used

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  • [1,2,4]-triazol [4,3-a] pyridines compound and synthesis method thereof
  • [1,2,4]-triazol [4,3-a] pyridines compound and synthesis method thereof
  • [1,2,4]-triazol [4,3-a] pyridines compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of [1,2,4]-triazolo[4,3-a]pyridine 3a, its structural formula is as follows:

[0048]

[0049]Add 0.5 mmol of α-ketoacid 1a and 0.5 mmol of 2-hydrazinopyridine 2a into a dry reaction tube, and sequentially add 0.1 mmol of potassium iodide, 1 mmol of sodium carbonate, 2 mL of 1,4-dioxane, 1 mmol of TBHP at 130 °C, reflux reaction for 12h. After the reaction, the reaction solution was extracted with ethyl acetate (10mL) and water three times, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 乙酸乙酯 :V 石油醚 = 5:1 (elution 20min), 2:1 (elution 20min), 1:1 (elution 50min) gradient elution to obtain the pure product. Its main physical and chemical properties are as follows:

[0050] Yellow solid, melting point 170-171°C; 1 H NMR (400MHz, CDCl 3 ):δ8.56(d,J=7.0Hz,1H),7.91(d,J=6.5Hz,2H),7.81(d,J=9.3Hz,1H),7.59-7.65(m,3H),7.41 -7.45(m,1H),7.02(t,J=6.7Hz,1H); 13 C NMR (100MHz, CDCl 3 ):δ150.0,146.0,129.9,129.2,128....

Embodiment 2

[0051] Example 2: Synthesis of [1,2,4]-triazolo[4,3-a]pyridine 3b, its structural formula is as follows:

[0052]

[0053] Add 0.5 mmol of α-ketoacid 1b and 0.5 mmol of 2-hydrazinopyridine 2a into a dry reaction tube, and sequentially add 0.1 mmol of potassium iodide, 1 mmol of sodium carbonate, 2 mL of 1,4-dioxane, 1 mmol of TBHP at 130 °C, reflux reaction for 12h. After the reaction, the reaction solution was extracted with ethyl acetate (10mL) and water three times, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 乙酸乙酯 :V 石油醚 = 5:1 (elution 20min), 2:1 (elution 20min), 1:1 (elution 60min) gradient elution to obtain the pure product. Its main physical and chemical properties are as follows:

[0054] Light yellow solid, melting point 160-161°C; 1 H NMR (400MHz, CDCl 3 ): δ8.26(d, J=7.1Hz, 1H), 7.82(d, J=9.3Hz, 1H), 7.72(d, J=8.2Hz, 2H), 7.39(d, J=7.9Hz, 2H ),7.24-7.29(m,2H),6.85(t,J=6.4Hz,1H),2.47(s,3H); 13 C NMR (100MHz, CDCl ...

Embodiment 3

[0055] Example 3: Synthesis of [1,2,4]-triazolo[4,3-a]pyridine 3c, its structural formula is as follows:

[0056]

[0057] Add 0.5 mmol of α-ketoacid 1c and 0.5 mmol of 2-hydrazinopyridine 2a into a dry reaction tube, and sequentially add 0.1 mmol of potassium iodide, 1 mmol of sodium carbonate, 2 mL of 1,4-dioxane, 1 mmol of TBHP at 130 °C, reflux reaction for 12h. After the reaction, the reaction solution was extracted with ethyl acetate (10mL) and water three times, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 乙酸乙酯 :V 石油醚 = 5:1 (elution 20min), 2:1 (elution 20min), 1:1 (elution 50min) gradient elution to obtain the pure product. Its main physical and chemical properties are as follows:

[0058] Light yellow solid, melting point 52-53°C; 1 H NMR (400MHz, CDCl 3 ): δ8.21(d, J=7.1Hz, 1H), 7.70(d, J=9.3Hz, 1H), 7.57(s, 1H), 7.51(d, J=7.6Hz, 1H), 7.36(t ,J=7.6Hz,1H),7.17-7.22(m,1H),6.79(t,J=7.3Hz,1H),2.37(s,3H); 13 C NMR (100MH...

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Abstract

The invention discloses a [1,2,4]-triazol [4,3-a] pyridines compound and a synthesis method thereof. The compound has a structure general formula shown as the formula (I), wherein R1 is selected fromaryl and heterocyclic groups; R2 is selected from hydrogen, alkyl, alkoxy, halogen or aryl. According to the synthesis method, alpha-ketonic acid and 2-hydrazinopyridine are used as raw materials; KIis used as a catalyst; Na2CO3 is used as alkali; TBHP is used as an oxidizing agent; 1,4-dioxane is used as a solvent; after a series of serial connection cyclization and decarboxylation aromatization, the [1,2,4]-triazol [4,3-a] pyridines compound is obtained. The [1,2,4]-triazol [4,3-a] pyridines compound is prepared under the condition of no transition metal and has the advantages that the reaction is efficient and fast; the conditions are mild; the substrate is simple and can be easily obtained; the applicability is wide; the reaction time is short; the yield is high, and the like; meanwhile, the post treatment of the reaction is simple and convenient; the harm to experiment operators is reduced; the environment-friendly effect is achieved; the green chemical requirements are met.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to [1,2,4]-triazolo[4,3-a]pyridine compounds and a synthesis method thereof. Background technique [0002] In nature, triazolopyridines are a very important class of fused heterocycles in nitrogen-containing heterocyclic compounds. Due to their important biological and pharmacological activities, triazolopyridines have attracted extensive research interest. In recent years, some [1,2,4]-triazolo[4,3-a]pyridine compounds have been reported to have obvious effects on inhibiting enzyme activity. [0003] With the continuous deepening of people's understanding of the use of [1,2,4]-triazolo[4,3-a]pyridine compounds, and the discovery of new and different substitution structures, the development of efficient and convenient synthesis processes to meet the needs of modern medicine Rapid development is an inevitable trend. At present, although there are many methods for synthe...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P7/02
CPCC07D471/04
Inventor 高鹏白梓静
Owner BAOJI UNIV OF ARTS & SCI
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