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Synthesis method of 4, 5-dicyanoimidazole derivative

A technology of dicyanoimidazole and synthesis method, applied in directions such as organic chemistry, can solve the problems of complicated operation, high cost, long reaction time and the like

Active Publication Date: 2021-09-10
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional method for synthesizing 4,5-dicyanoimidazole derivatives is complex in operation, long in reaction time, with many by-products and high cost

Method used

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  • Synthesis method of 4, 5-dicyanoimidazole derivative
  • Synthesis method of 4, 5-dicyanoimidazole derivative
  • Synthesis method of 4, 5-dicyanoimidazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] To the reactor was added 0.2 mmol A, 10 mg OMS-2 catalyst, and 1.5 mL DMF. After mixing uniformly, the reaction was stirred at 120°C for 2 hours, and the progress of the reaction was monitored by TLC. After the reaction was completed, it was cooled to room temperature, and the crude product was purified by column chromatography to obtain the target product I-1 with a yield of 22%.

Embodiment 2

[0024]

[0025] Add 0.3 mmol A, 6 mg CuO to the reactor x / OMS-2 catalyst, and then add 1.5 mL of toluene. After mixing uniformly, the reaction was stirred at 120°C for 2 hours, and the progress of the reaction was monitored by TLC. After the reaction was completed, it was cooled to room temperature, and the crude product was purified by column chromatography. The target product I-1 was not obtained, and the yield was 0%.

Embodiment 3

[0027]

[0028] Add 0.3 mmol A, 6 mg CuO to the reactor x / OMS-2 catalyst, and 1.5 mL of DMF was added. After mixing uniformly, the reaction was stirred at 120°C for 2 hours, and the progress of the reaction was monitored by TLC. After the reaction was completed, it was cooled to room temperature, and the crude product was purified by column chromatography to obtain the target product I-1 with a yield of 93.5%.

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Abstract

The invention relates to a synthesis method of a 4, 5-dicyanoimidazole derivative under the catalysis of a heterogeneous copper-loaded manganese oxide octahedral molecular sieve (CuOx / OMS-2), which comprises the following steps of: in an organic solvent, taking a diamino maleic nitrile derivative as a substrate, and reacting under the catalysis of CuOx / OMS-2 to obtain the 4, 5-dicyanoimidazole derivative. In the novel synthesis method, the raw materials and the catalyst are simple and easy to obtain, the atom economic benefit is high, the heterocyclic ring yield is high, and the operation is simple. The structure of the 4, 5-dicyanoimidazole derivative provided by the invention is as shown in a structural formula I in the specification, wherein R is a benzene ring, thiophene, pyrrole, naphthalene, tetraphenylethylene, triphenylamine or a benzene ring substituted by any one or more substituent groups of alkyl, OMe, CF3, OH and X (halogen).

Description

technical field [0001] The invention relates to a heterogeneous copper-supported manganese-oxygen octahedral molecular sieve (CuO x / OMS-2) A method for synthesizing 4,5-dicyanoimidazole derivatives, which belongs to the technical field of organic synthesis. Background technique [0002] Manganese oxide octahedral molecular sieve (OMS-2) is another molecular sieve material that has received a lot of attention and research after zeolite-type tetrahedral molecular sieve. It has unique physical and chemical properties and porous structure, and can be used as a catalyst in the field of organic synthesis. The OMS-2 material contains only a small amount of trivalent manganese ions (Mn 3+ ), most of the manganese is in the form of tetravalent manganese ions (Mn 4+ ), so OMS-2 has good redox properties. After Cu loading, CuO x / OMS-2 showed more excellent catalytic performance. 4,5-Dicyanoimidazole derivatives are used as raw materials for organic synthesis or pharmaceutical in...

Claims

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Application Information

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IPC IPC(8): C07D233/90C07D409/04
CPCC07D233/90C07D409/04
Inventor 郑开波肖宇峰陈慧刘湘余威王丽红
Owner CHINA THREE GORGES UNIV
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