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Synthesis method of benzopyrone and imidazopyridine compound

A technology of imidazopyridine and benzopyrone, which is applied in the field of synthesis of benzopyrone imidazopyridine compounds, can solve the problems of compound synthesis methods and reports, and avoid waste of resources and environmental pollution , high reaction efficiency and wide application range

Active Publication Date: 2016-06-01
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no report about the synthesis method of this type of compound

Method used

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  • Synthesis method of benzopyrone and imidazopyridine compound
  • Synthesis method of benzopyrone and imidazopyridine compound
  • Synthesis method of benzopyrone and imidazopyridine compound

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Experimental program
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Embodiment 1

[0019]

[0020] In a 15mL Schlenk tube add 1a (0.5mmol, 136.6mg), DMSO (2mL), tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 , 0.025mmol, 23mg), Cu(OAc) 2 (0.25mmol, 45.4mg), triphenylphosphine (0.075mmol, 20mg) and 1,4-diazabicyclo[2.2.2]octane (DABCO, 1.5mmol, 168.3mg). Evacuate and fill with CO, repeat three times. Stir the reaction for 12 hours in an oil bath at 150° C. under a CO atmosphere of 1 atm. The reaction was quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain the target product 2a (21.2mg, 18%). The characterization data of this compound are as follows: 1 HNMR (400MHz, CDCl 3 )δ:7.19(t, J =7.2Hz,1H),7.43(t, J =7.6Hz,1H),7.50(d, J =8.4Hz,1H),7.55-7.60(m,1H),7.63-7.67(...

Embodiment 2

[0022] In a 15mL Schlenk tube add 1a (0.5mmol, 136.6mg), DMSO (2mL), Pd2 (dba) 3 (0.025mmol, 23mg), Cu(OAc) 2 (0.5mmol, 90.8mg), triphenylphosphine (0.075mmol, 20mg) and DABCO (1.5mmol, 168.3mg). Evacuate and fill with CO, repeat three times. Stir the reaction for 12 hours in an oil bath at 150° C. under a CO atmosphere of 1 atm. The reaction was quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain the target product 2a (35.4mg, 30%).

Embodiment 3

[0024] In a 15mL Schlenk tube add 1a (0.5mmol, 136.6mg), DMSO (2mL), Pd 2 (dba) 3 (0.025mmol, 23mg), Cu(OAc) 2 (1.0mmol, 181.6mg), triphenylphosphine (0.075mmol, 20mg) and DABCO (1.5mmol, 168.3mg). Evacuate and fill with CO, repeat three times. Stir the reaction for 12 hours in an oil bath at 150° C. under a CO atmosphere of 1 atm. The reaction was quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain the target product 2a (24.8mg, 21%).

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Abstract

The invention discloses a synthesis method of a benzopyrone and imidazopyridine compound. The benzopyrone and imidazopyridine compound is directly obtained through the one-pot serial-connection reaction under transient metal catalysis, the benzopyrone structure is established in the one-pot reaction, structure units of benzopyrone and imidazopyridine are subjected to ring fusion, reaction efficiency is high, the resource waste and environment pollution caused by the application of various reagents in the multi-step reaction, the purification of reaction intermediates in multiple steps and the like are avoided, raw materials are easy to prepare, reaction operation is easy and convenient, and the application range of substrates is wide.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of benzopyrone imidazopyridine compounds. Background technique [0002] Benzo-α-pyrone and its derivatives, that is, coumarin compounds, are not only widely distributed in nature, but also have significant biological and pharmaceutical activities such as anti-coagulation, anti-cancer and anti-HIV. At the same time, because these compounds generally have the characteristics of strong fluorescence, good photostability, and high photoluminescence quantum efficiency, they are often used as laser dyes, fluorescent whitening agents, fluorescent probes, and nonlinear optical materials. On the other hand, imidazopyridine is an important class of nitrogen-containing fused heterocyclic rings, and many imidazopyridine derivatives have anti-tumor, anti-dopamine receptor and anti-herpes virus effects. In recent years, imidazopyridine compounds have al...

Claims

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Application Information

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IPC IPC(8): C07D491/147
CPCC07D491/147
Inventor 张新迎范学森张举郭胜海
Owner HENAN NORMAL UNIV
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