Method for preparing imidazolone derivative through dehydrogenation conversion of dihydric alcohol under catalysis of manganese

By using PNP-type Pincer manganese catalyst to catalyze urea and alcohol compounds, the problems of high cost and low reaction efficiency of precious metal catalysts were solved, and efficient synthesis of imidazolinone derivatives was achieved with high yield and good atom economy.

CN120647585APending Publication Date: 2025-09-16HENAN AGRICULTURAL UNIVERSITY
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Patent Information

Application Number
CN202510791977.8
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-06-13
Publication Date
2025-09-16

AI Technical Summary

Technical Problem

In the existing technology for synthesizing imidazolone derivatives, the cost of precious metal catalysts is high, the reaction efficiency is low, and the traditional method is not atom-economical and sustainable enough.

Method used

PNP-type Pincer manganese catalyst is used to catalyze the dehydrogenation coupling reaction of urea and alcohol compounds to synthesize imidazolide derivatives. The use of Mn pincer catalyst reduces costs and improves reaction efficiency.

Benefits of technology

The method reduces costs while improving the reaction efficiency of imidazolidone derivatives, with a yield of up to 99%. It also has good biocompatibility, a wide range of raw material sources, and wide applicability.

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Abstract

The invention provides a method for preparing imidazolone derivatives through dehydrogenation conversion of dihydric alcohol under the catalysis of manganese, belongs to the technical field of synthetic chemistry, and aims to solve the technical problems of high cost and low reaction efficiency of a noble metal catalyst in synthesis of imidazolone derivatives from urea and alcohol. The preparation method comprises the following steps: dispersing and dissolving a urea compound, an alcohol compound, an alkaline auxiliary agent and a Pincer type PNP manganese complex catalyst into an organic solvent, and reacting to obtain a target compound after the reaction is finished. The Mn pincerlike catalyst is adopted, so that the reaction efficiency is improved while the cost is reduced.
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Claims

1. A method for preparing imidazolone derivatives by manganese-catalyzed dehydrogenation of diols, characterized in that: The method comprises the following steps: dispersing and dissolving a urea compound, an alcohol compound, an alkaline auxiliary agent and a Pincer-type PNP manganese complex catalyst in an organic solvent to carry out a reaction, and obtaining a target compound after the reaction is completed.

2. The method for preparing imidazolidinone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 1, characterized in that: The urea compound and the alcohol compound have a structure as shown in Formula I: In formula I, R1 is an alkyl group, a cyclohexane group or a group containing a phenyl group, and R2 and R3 are independently selected from an alkyl group, a cyclopentyl group or a cycloethyl group.

3. The method for preparing imidazolidinone derivatives by dehydrogenation of diols catalyzed by manganese according to claim 1 or 2, characterized in that: The PNP-type Pincer manganese catalyst is shown in Formula II: R 4 is -H, X is -Br, and R is isopropyl, cyclohexyl, tert-butyl or phenyl.

4. The method for preparing imidazolidinone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 3, characterized in that: The PNP-type Pincer manganese catalyst is catalyst [Mn]-1, catalyst [Mn]-2, catalyst [Mn]-3 or catalyst [Mn]-4, and has the following structure:

5. The method for preparing imidazolidinone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 4, characterized in that: The alkaline auxiliary agent is one or more of alkali metal hydroxides, alkali metal alkoxides, alkali metal carbonates and alkali metal organic salts.

6. The method for preparing imidazolidinone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 5, characterized in that: The alkali metal hydroxide is sodium hydroxide or potassium hydroxide; the alkali metal alkoxide is sodium ethoxide, sodium tert-butoxide or potassium tert-butoxide; and the alkali metal carbonate is sodium carbonate or cesium carbonate.

7. The method for preparing imidazolone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 1, characterized in that: The organic solvent is one or more of dioxane, toluene or tetrahydrofuran.

8. The method for preparing imidazolidinone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 1, characterized in that: The ratio of the amount of the urea compound to the alcohol compound is 1:1.5-2; the amount of the alkaline auxiliary agent added is 5-15 mol% of the urea compound.

9. The method for preparing imidazolone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 1, characterized in that: The ratio of the urea compound to the organic solvent is 0.5 mmol: 0.1-1 mL.

10. The method for preparing imidazolone derivatives by manganese-catalyzed dehydrogenation of diols according to claim 1, characterized in that: The addition amount of the Pincer type PNP manganese complex catalyst is 0.5-2 mol% of the urea compound.

Citation Information

Patent Citations

  • Application of Pincer type PNP manganese complex catalyst

    CN117362216A