Method for preparing tetrasubstituted furan compound based on carbon-hydrogen bond activation

A compound and tetra-substituted technology, applied in the field of preparing tetra-substituted furan compounds, can solve the problems of seriousness, pollution and high price, and achieve the effects of realizing reaction conditions, easy reaction conditions and less dosage

Active Publication Date: 2018-12-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above methods usually require the use of noble metals, which are expensive and highly polluting, which limits their application. Therefore, it is of great significance to develop new catalytic systems to easily and efficiently construct tetrasubstituted furan compounds.

Method used

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  • Method for preparing tetrasubstituted furan compound based on carbon-hydrogen bond activation
  • Method for preparing tetrasubstituted furan compound based on carbon-hydrogen bond activation
  • Method for preparing tetrasubstituted furan compound based on carbon-hydrogen bond activation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Cu(OTf) 2 Complexation with L-1 is used as a catalyst to catalyze the reaction to generate tetrasubstituted furan addition product 5-methyl-2,4-diphenylfuran-3-carboxylic acid ethyl ester Ⅰ-1.

[0059] Add metal precursor Cu(OTf) to the reaction flask 2 (0.01mmol, 5mol%) and o-phenanthroline monohydrate ligand L-1 (0.011mmol, 5.5mol%), added 1.0mL of anhydrous dichloromethane under nitrogen protection, and stirred at room temperature for 1 hour. Then phenylpropyne Ⅲ-1 (0.44mmol, 2.2equiv), ethyl benzoyl acetate Ⅱ-1 (0.2mmol, 1.0equiv), Et 3 N (0.24mmol, 1.2equiv) and Ag 2 CO 3 (0.24mmol, 1.2equiv) was dissolved in 2.0mL of anhydrous dichloromethane, and then the solution was added to the above-mentioned stirred catalyst solution under nitrogen protection, and the reaction was stirred at 40°C for 24h; then DBU (0.24mmol, 1.2 equiv), continue to reflux at 40°C, and monitor the reaction by TLC. After the reaction was completed, it was concentrated under reduced pressu...

Embodiment 2

[0064] L-2 acts as a ligand to react to produce ethyl 5-methyl-2,4-diphenylfuran-3-carboxylate Ⅰ-1.

[0065] The ligand L-1 in Example 1 is replaced by the ligand L-2, and the rest are the same as in Example 1. The reaction gave compound I-1 in 41% yield.

[0066] The structural formula of L-2 is as follows:

[0067]

Embodiment 3

[0069] L-3 reacted as a ligand to generate the product ethyl 5-methyl-2,4-diphenylfuran-3-carboxylate Ⅰ-1.

[0070] The ligand L-1 in Example 1 is replaced by the ligand L-3, and the rest are the same as in Example 1. The reaction gave compound I-1 in 64% yield.

[0071] The structural formula of L-3 is as follows:

[0072]

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Abstract

The invention provides a method for preparing a tetrasubstituted furan compound based on carbon-hydrogen bond activation, belongs to the field of organic synthesis, and relates to a method for synthesizing a tetrasubstituted furan compound through a [3+2] cycloaddition reaction of beta-ketoester and a propargyl compound by usiong a C-H bond activation strategy, wherein the used copper catalyst isgenerated in situ from a copper salt and a 1,10-azaphenanthrene ligand in various polar and non-polar solvents. According to the present invention, various tetrasubstituted furan compounds can be conveniently synthesized, the yield can be up to 94%, and the method has characteristics of simple operation, easily available raw materials, wide application range of substrate, high reaction activity and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing tetrasubstituted furan compounds based on carbon-hydrogen bond activation. Background technique [0002] Furan is a very important five-membered heterocyclic compound. Many furan ring derivatives have biological and pharmacological activities, and are widely used in medicine, pesticides and biochemistry. As a derivative of furan, multi-substituted furan is not only a structural unit of natural products and important drugs, but also an important intermediate of organic synthesis [(a) Dean, F.M.Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963, pp.1 ~28. (b) Donnelly, D.M.X.; Meegan, M.J. In Comprehensive Hetero-cyclic Chemistry, Vol.4, Ed.: Katrizky, A.R., Pergamon Press, New York, 1984, pp.657~712. (c) Landquist, J.K.In Comprehensive Heterocyclic Chemistry, Vol.1, Ed.: Katrizky, A.R., Pergamon Press, New York, 1984, pp.144~1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C07D409/04B01J31/22
CPCC07D307/68C07D409/04B01J31/1805B01J31/1815B01J31/183B01J2531/0241B01J2531/16B01J2231/324
Inventor 胡向平刘振婷
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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