Synthesis method of 1,2,4-triazolohetercyclic compound
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A technology for aldehyde compounds and heterocycles, which is applied in the field of synthesizing 1,2,4-triazoloheterocycles, can solve the problems of expensive reagents, toxic and harmful prices, etc., and achieves simple reaction system and high total yield , easy to obtain effect
Active Publication Date: 2017-12-15
ZHEJIANG UNIV OF TECH
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[0004] The purpose of the invention is to provide a method for synthesizing 1,2,4-triazolo heterocyclic compounds in one step through 2-hydrazino heterocyclic compounds and aldehyde compounds, solving the problem of synthesizing 1,2,4-triazoles in the past And heterocyclic compounds require the use of toxic, harmful or expensive reagents
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Embodiment 1
[0021] Dissolve 2-hydrazinopyridine (65.5mg, 0.6mmol) and benzaldehyde (51μL, 0.5mmol) in 5mL of acetonitrile solvent, stir and react at 25°C for 1 hour, then add tetrabutylammonium tetrafluoroborate (164.6mg , 0.5mmol), 4mL acetonitrile, 1mL water, and then install a graphite carbon rod electrode as the anode, and a platinum sheet electrode as the cathode, turn on the power, set the current to 10mA, and stop the power after 4 hours. Cool to room temperature, wash with water, extract with dichloromethane, dry over anhydrous sodium sulfate, filter, concentrate, and column chromatography to obtain the product 3-phenyl-[1,2,4]triazolo[4,3-a]pyridine 83.9 mg, the yield is 86%, and the product is an off-white solid. m.p.:171–173°C; 1 H NMR (500MHz, CDCl 3 )δ8.30(dt,J=7.0,1.2Hz,1H),7.88–7.82(m,3H),7.63–7.55(m,3H),7.31(ddd,J=9.3,6.5,1.1Hz,1H) ,6.89(td,J=6.8,1.1Hz,1H)ppm.
Embodiment 2
[0023] According to the method described in Example 1, the difference is that the amount of 2-hydrazinopyridine is 54.6mg (0.5mmol), to obtain the product 3-phenyl-[1,2,4]triazolo[4,3-a ] Pyridine 58.6mg, the yield is 60%, and the product is off-white solid.
Embodiment 3
[0025] According to the method described in Example 1, the difference is that the amount of 2-hydrazinopyridine is 81.88mg (0.75mmol), to obtain the product 3-phenyl-[1,2,4]triazolo[4,3-a ] Pyridine 78.0 mg, the yield was 80%, and the product was off-white solid.
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Abstract
The invention provides a method for synthesizing a 1,2,4-triazolohetercyclic compound. The method comprises the following steps: dissolving a 2-hydrazinohetercyclic compound (I) and an aldehyde compound (II) into acetonitrile A; stirring at 25 DEG C to 80 DEG C and reacting for 1h to 8h; then adding tetrabutylammonium tetrafluoroborate, acetonitrile B and water; taking a graphite carbon rod as an anode and a platinum sheet as a cathode; switching on a power supply and electrifying for 3h to 8h, wherein the current strength is 15mA/mmol to 30mA/mmol according to the amount of substance of the aldehyde compound (II); carrying out post-treatment on a reaction solution to obtain the product 1,2,4-triazolohetercyclic ring compound (III). The method has the advantages of simple reaction system, easiness for obtaining raw materials and high total yield; the 2-hydrazinohetercyclic compound and the aldehyde compound are subjected to electrochemical catalysis to obtain the 1,2,4-triazolohetercyclic compound in one step; only one water molecule and one hydrogen molecule are removed and the atomic economy is extremely high; the formula is shown in the description.
Description
(1) Technical field [0001] The invention relates to a method for synthesizing 1,2,4-triazolo heterocyclic compounds, which is to efficiently synthesize 1,2,4-triazolo by reacting 2-hydrazino heterocyclic compounds with aldehyde compounds Methods for Heterocyclic Compounds. (2) Background technology [0002] 1,2,4-Triazolo[4,3-a]pyridine and related heterocyclic compounds have important applications in pharmacy, agrochemical and materials science. In the field of pharmacy, molecules with a skeleton of 1,2,4-triazolo[4,3-a]pyridine have been reported to have a wide range of biological activities, such as antidepressant, antipsychotic, anticonvulsant, antibacterial, anti-inflammatory , antithrombotic, antiproliferative (Eur.J.Med.Chem., 2010, 45,352-366.Bioorg.Med.Chem.Lett., 2012, 22, 3431-3436.J.Med.Chem., 2012,55, 8770-8789). [0003] At present, there are two main methods for the synthesis of such compounds: (1) Obtained by oxidative cyclization of the hydrazone formed b...
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