A kind of synthetic method of 4,5-dicyanoimidazole derivatives

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

Active Publication Date: 2022-08-05
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A kind of synthetic method of 4,5-dicyanoimidazole derivatives
  • A kind of synthetic method of 4,5-dicyanoimidazole derivatives
  • A kind of synthetic method of 4,5-dicyanoimidazole derivatives

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Experimental program
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Effect test

Embodiment 1

[0022]

[0023] 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

[0025]

[0026] 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

[0028]

[0029] 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 present invention relates to heterogeneous copper-supported manganese-oxygen octahedral molecular sieves (CuO x / OMS-2) The synthetic method of catalyzing 4,5-dicyanoimidazole derivatives, the method is in organic solvent, with a kind of diaminomaleonitrile derivative as substrate, in CuO x The reaction occurs under the catalytic condition of / OMS-2 to obtain a 4,5-dicyanoimidazole derivative. In the new synthesis method, the raw materials and catalysts are simple and easy to obtain, the atomic economic benefit is high, the yield of heterocycles is high, and the operation is simple. The structure of the 4,5-dicyanoimidazole derivatives involved in the present invention is shown in structural formula I. Wherein R is benzene ring, thiophene, pyrrole, naphthalene, tetraphenylene, triphenylamine, by alkyl, OMe, CF 3 , OH, X (halogen) benzene ring substituted by any one or more substituents.

Description

technical field [0001] The invention relates to a heterogeneous copper-supported manganese-oxygen octahedral molecular sieve (CuO x / OMS-2) A synthesis method for catalyzing 4,5-dicyanoimidazole derivatives, belonging 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 pharmaceutica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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