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Synthetic method of imidazole-containing fused heterocyclic compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of harsh reaction conditions, difficult to obtain raw materials, and high environmental factors, and achieve the effects of mild reaction conditions, wide application range, and avoidance of environmental pollution.

Inactive Publication Date: 2020-05-12
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In view of the importance of this type of compound, researchers have developed a variety of methods for synthesizing imidazole-containing fused heterocyclic compounds, but these developed methods have disadvantages such as unavailable raw materials, many reaction steps, harsh reaction conditions, and high environmental factors. , making their application in actual production subject to certain restrictions

Method used

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  • Synthetic method of imidazole-containing fused heterocyclic compound
  • Synthetic method of imidazole-containing fused heterocyclic compound
  • Synthetic method of imidazole-containing fused heterocyclic compound

Examples

Experimental program
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Effect test

Embodiment 1

[0022]

[0023] Add 1a (44mg, 0.2mmol), 2a (37mg, 0.3mmol), methanol (1mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer in sequence to a 15mL pressure tube (6mg, 0.01mmol) and zinc acetate (37mg, 0.2mmol), then seal the pressure tube and place it in an oil bath at 120°C for 12h. After the reaction, cooled to room temperature, suction filtered, spin-dried, and separated by silica gel column (volume ratio: petroleum ether / ethyl acetate=2 / 1) to obtain the white solid product 3aa (5 mg, 8%). The characterization data of this compound are as follows: 1H NMR (400MHz, CDCl 3 )δ: 2.89(t, J=6.8Hz, 2H), 3.47(t, J=6.8Hz, 2H), 3.76(s, 3H), 6.96(t, J=6.8Hz, 1H), 7.46-7.50( m,1H),7.62-7.66(m,1H),7.68-7.71(m,1H),7.82(d,J=9.2Hz,1H),8.40(s,1H),8.50(d,J=6.8Hz ,1H),8.80-8.84(m,2H). 13 C NMR (100MHz, CDCl 3 )δ: 28.7, 36.3, 52.0, 112.1, 113.5, 118.1, 122.4, 123.1, 124.7, 126.88, 126.93, 127.6, 129.0, 129.20, 129.25, 144.2, 149.2, 173.7, 200.6. HRMS calcd for C 20 h 17 N 2 o...

Embodiment 2

[0025] Add 1a (44mg, 0.2mmol), 2a (37mg, 0.3mmol), methanol (1mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer in sequence to a 15mL pressure tube (6mg, 0.01mmol) and acetic acid (12mg, 0.2mmol), then seal the pressure tube and place it in an oil bath at 120°C for 12h. After the reaction, cooled to room temperature, suction filtered, spin-dried, and separated by silica gel column (volume ratio: petroleum ether / ethyl acetate=2 / 1) to obtain the white solid product 3aa (34 mg, 51%).

Embodiment 3

[0027] Add 1a (44mg, 0.2mmol), 2a (37mg, 0.3mmol), methanol (1mL), dichloro(pentamethylcyclopentadienyl) rhodium(III) dimer in sequence to a 15mL pressure tube (6mg, 0.01mmol) and potassium acetate (20mg, 0.2mmol), then seal the pressure tube and place it in an oil bath at 120°C for 12h. After the reaction, cooled to room temperature, suction filtered, spin-dried, and separated by silica gel column (volume ratio: petroleum ether / ethyl acetate=2 / 1) to obtain the white solid product 3aa (22 mg, 33%).

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Abstract

The invention discloses a synthetic method of an imidazole-containing fused heterocyclic compound. According to the invention, a 3-formyl-2-arylimidazo [1, 2-a] pyridine or 3-formyl-2-heteroarylimidazo [1, 2-a] pyridine compound, a 5-formyl-6-arylimidazo [2, 1-b] thiazole or 5-formyl-6-heteroarylimidazo [2, 1-b] thiazole compound or a 3-formyl-2-arylbenzo [d] imidazo [2, 1-b] thiazole or 3-formyl-2-heteroarylbenzo [d] imidazo [2, 1-b] thiazole compound and a cyclic alpha-diazo-1, 3-diketone compound are subjected to a cascade reaction to synthesize the target product, namely the imidazole-containing fused heterocyclic compound. The synthetic method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and is suitablefor industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing imidazole-containing condensed heterocyclic compounds. Background technique [0002] Imidazoles are an important class of nitrogen-containing heterocyclic compounds, which have biological activities such as anticancer, antimalarial, antitumor, antibacterial, and antiviral. In addition, imidazole is also the main structural unit of many natural products and organic functional molecules. Imidazopyridine compounds are special imidazole-containing fused heterocyclic compounds, which are widely used in medicinal chemistry, material science and other fields. In the field of medicinal chemistry, there are currently many marketed drugs containing imidazopyridine skeletons, such as: Zolpidem (Zolpidem), Olprinone (Olprinone), Saripidem (Saripidem), Necopidem (Necopidem )wait. In addition, this type of compound also has biological activities such as a...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 沈娜娜李彬范学森张新迎杨玉洁
Owner HENAN NORMAL UNIV
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