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Novel method for synthesizing imidazolidine heterocycle

A synthetic method, imidazolidine technology, which is applied in the new synthesis field of imidazolidine heterocyclic compounds, and can solve the problems of expensive use and low yield

Inactive Publication Date: 2013-09-04
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the synthetic methods reported in the literature need to go through multi-step reactions, use expensive catalysts sensitive to air or humidity, and the yield is not high [(a) Alma Viso, Roberto Fernandez de la Pradilla, Ana Garcia, et al.Highly Diastereoselective[ 3+2] Cycloadditions between Nonracemic p-Tolylsulfimines and Iminoesters: An Efficient Entry to Enantiopure Imidazolidines and Vicinal Diaminoalcohols [J]. Chem. Eur. J, 2003, 9, 2867-2876. (b) Doug E. Frantz, Louis Morency , Arash Soheili, et al.Synthesis of Substituted Imidazoles via Organocatalysis[J].Org.Lett, 2004, 5(6), 843-846.]

Method used

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  • Novel method for synthesizing imidazolidine heterocycle
  • Novel method for synthesizing imidazolidine heterocycle
  • Novel method for synthesizing imidazolidine heterocycle

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Experimental program
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Effect test

Embodiment 1

[0013]

[0014] Synthesis of Imidazolidine I-1 - Using CuCl as Catalyst and DCM as Solvent

[0015] 0.5 mmol of CuCl was added to 10.0 mmol of A and 5.0 mmol of methyl propiolate in dichloromethane, and the reactant was stirred at 25° C. for 12 h. The reaction solution was filtered through silica gel to remove CuCl, and the filtrate was concentrated and washed with CH 3 OH recrystallized to obtain a white solid, yield: 93%.

Embodiment 2

[0017]

[0018] Synthesis of Imidazolidine I-1 - Using CuBr as Catalyst and 1,2-Dichloroethane as Solvent

[0019] 0.5 mmol of CuBr was added to 10.0 mmol of A and 5.0 mmol of methyl propiolate in 1,2-dichloroethane, and the reactant was stirred at 25°C for 12 h. The reaction solution was filtered through silica gel to remove CuBr, and the filtrate was concentrated and washed with CH 3 OH recrystallized to obtain a white solid, yield: 81%.

Embodiment 3

[0021]

[0022] Synthesis of Imidazolidine I-2 - Using CuCl as Catalyst and Toluene as Solvent

[0023] Add 0.5 mmol of CuCl to 10.0 mmol of B and 5.0 mmol of methyl propiolate in toluene, and stir the reactant at 25°C for 12 h. The reaction solution was filtered through silica gel to remove CuCl, the filtrate was concentrated, and the crude product was separated by column chromatography to obtain a white solid with a yield of 63%.

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Abstract

The invention relates to a novel method for synthesizing two imidazolidine heterocyclic compounds. According to the method, in an organic solvent, imine and alkyne are taken as substrates, and multicomponent reaction occurs under the catalysis condition of copper (I), so that imidazolidine heterocyclic compounds are formed. The synthetic method has the advantages as follows: starting materials and a catalyst are cheap and easy to obtain, the atomic economic benefit is high, the heterocyclic yield is high, the limit to substitution types of a functional group is smaller, the reaction condition is mild, the operation is simple, and the like. Structures of two imidazolidine heterocyclic compounds are shown as structural formulae I and II, wherein R1, R3 and R5 are independently selected from a benzene ring, a benzene ring substituted by one or more substituent groups of C1-C3 alkyl groups, OMe, NO2, CF3 and X (halogen), and a naphthenic base; R2 is independently selected from COOMe, COOEt and COO(CH2)nCH3, and n=1-10; and R4 is independently selected from a benzene ring and a benzene ring or a heterocyclic ring substituted by one or more substituent groups of C1-C3 alkyl groups, OMe, NO2, CF3 and X (halogen).

Description

technical field [0001] The present invention relates to a new synthesis method of imidazolidine heterocyclic compounds. The key point of the present invention is to obtain imidazolidine heterocyclic compounds by adopting a one-pot method and utilizing multi-component reaction of imine and alkyne under the catalysis of copper (I). ring compounds. The synthesis method has mild conditions, simple operation, less restriction on the substitution type of functional groups, and high heterocycle yield. In addition, the raw materials and the catalyst used in the synthesis method are cheap and easy to obtain, and have good industrialization prospects. technical background [0002] Nitrogen heterocycles and their derivatives have a wide range of biological activities, and have extremely important application values ​​and occupy a very important position in various fields such as medicine, pesticides and life sciences. Among nitrogen heterocycles, imidazolidines occupy a unique positi...

Claims

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Application Information

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IPC IPC(8): C07D233/26C07D405/04
Inventor 李玉峰卜洪忠吴正光石洁王兴龙顾嘉超
Owner NANJING UNIV OF TECH