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A kind of synthetic method of indenonoimidazopyridine compound

A technology for imidazopyridine and ketone compounds, which is applied in organic chemistry and other fields, can solve problems such as reports and no compound synthesis methods, and achieve the effects of simple reaction operation, avoiding resource waste and environmental pollution, and wide application range

Active Publication Date: 2017-12-29
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no report about the synthetic method of this class of compounds

Method used

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  • A kind of synthetic method of indenonoimidazopyridine compound
  • A kind of synthetic method of indenonoimidazopyridine compound
  • A kind of synthetic method of indenonoimidazopyridine compound

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Experimental program
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Effect test

Embodiment 1

[0010]

[0011] In a 15 mL Schlenk tube add 1a (0.5 mmol, 136.6 mg), DMSO (2 mL), Pd(OAc) 2 (0.05 mmol, 11.2 mg), n-butylbis(1-adamantyl)phosphine (BDAP, 0.075 mmol, 2.6 mg) and 1,4-diazabicyclo[2.2.2]octane (DABCO, 1.5 mmol, 168.3 mg). Evacuate and fill with CO, repeat three times. In an oil bath at 120°C under a CO atmosphere of 1 atm, the reaction was stirred for 12 hours, then quenched by adding 10 mL of saturated ammonium chloride solution, extracted with ethyl acetate (6 mL × 3), and then the organic phase was mixed with water and saturated saline Washed successively and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain the target product 2a (22 mg, 20%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ: 6.98 (t, J = 6.8 Hz, 1H), 7.19 (t, J = 7.6 Hz,1H), 7.29-7.40 (m, 4H), 7.60 (d, J = 8.8 Hz, 1H), 8.38 (d, J = 6.4 Hz, ...

Embodiment 2

[0013] In a 15 mL Schlenk tube add 1a (0.5 mmol, 136.6 mg), DMSO (2 mL), Pd(OAc) 2 (0.05 mmol, 11.2 mg), triphenylphosphine (0.075 mmol, 19.7 mg) and DABCO (1.5 mmol, 168.3 mg). Evacuate and fill with CO, repeat three times. Stir the reaction in an oil bath at 120°C under a CO atmosphere of 1 atm for 12 hours, add 10 mL of saturated ammonium chloride solution to quench the reaction, extract with ethyl acetate (6 mL × 3), and then the organic phase is washed with water and saturated brine successively Washed and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain the target product 2a (33 mg, 33%).

Embodiment 3

[0015] In a 15 mL Schlenk tube add 1a (0.5 mmol, 136.6 mg), DMSO (2 mL), Pd(OAc) 2 (0.05 mmol, 11.2 mg), tricyclohexylphosphine (TCHP, 0.075 mmol, 21 mg) and DABCO (1.5 mmol, 168.3 mg). Evacuate and fill with CO, repeat three times. Stir the reaction in an oil bath at 120°C under a CO atmosphere of 1 atm. After stirring for 12 hours, add 10 mL of saturated ammonium chloride solution to quench the reaction, extract with ethyl acetate (6 mL × 3), and then the organic phase is sequentially washed with water and saturated brine. Washed and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=2 / 1) to obtain the target product 2a (31.9 mg, 29%).

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Abstract

The invention discloses a method for synthesizing indene ketone and imidazole and pyridine compounds. The method comprises the steps that 2-(2- bromophenyl) imidazole [1, 2-alpha] pyridine or a derivative thereof is dissolved in solvent, then catalysts, ligands and alkali are added, a reaction is conducted in oil bath at the temperature of 120-160 DEG C under the atmosphere of 1atm of CO, and the 11H-indene [1', 2': 4, 5] imidazole [1, 2-alpha] pyridine-11-ketone compounds are obtained. The synthesis process is simple and efficient, a series-connection reaction under catalysis of transition metal is utilized, the indene ketone and imidazole and pyridine compounds are obtained through one step, in other words, an indene ketone structure is constructed while indanone and an imidazole and pyridine structural unit are linked together, resource waste and environmental pollution caused by application of multiple types of reagent andpurification treatment of the ligands in all steps of the reaction and the like in multiple steps of the reaction are avoided, raw materials are easy to prepare, the reaction is easy and convenient to operate, and the adaptability range of a substrate 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 indenonoimidazopyridine compounds. Background technique [0002] Indanone compounds not only widely exist in natural products, medicines and other biologically active molecules, but also are very important intermediates in organic synthesis, and are widely used in the production of fine organic chemicals, such as the preparation of dyes, photochromic, organic light-emitting materials, etc. Among them, it has high economic value. Therefore, indanone compounds have very important applications in biomedicine and industry. On the other hand, imidazopyridine, as an important class of nitrogen-containing fused heterocyclic rings, not only shows strong biological activity, but also is the main structural unit of some drugs (such as: anti-HIV drug GSK812397, vasodilator drug Oprinone, etc.) , and has been widely used in the fields of biologic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 范学森张举张新迎郭胜海
Owner HENAN NORMAL UNIV
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