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Cyclopropyl alkenyl amide derivative and synthesizing method thereof

A technology of cyclopropenamide and derivatives, which is applied in chemical instruments and methods, formation/introduction of mercapto/thioether groups, preparation of organic compounds, etc., can solve the problem of weak atom economy, numerous preparation steps, raw materials Problems such as activation are required to achieve the effects of wide applicability, cheap and easy-to-obtain preparation raw materials, and good stereoselectivity

Active Publication Date: 2017-05-31
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

[0005] The traditional preparation of cyclopropylacrylamide derivatives has many steps, the raw materials need to be activated, the reaction conditions are harsh, and the atom economy is not strong.

Method used

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  • Cyclopropyl alkenyl amide derivative and synthesizing method thereof
  • Cyclopropyl alkenyl amide derivative and synthesizing method thereof
  • Cyclopropyl alkenyl amide derivative and synthesizing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047]

[0048] Weigh 4a (123.5mg, 0.5mmol) and iodobenzene acetate (193.3mg, 0.6mmol) into a 25mL Schlenk reaction flask, add 5mL of DCE solvent under air, and stir the reaction at 25°C for 2 hours. After the reaction, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1) to obtain the white solid target Product 1a (112.9 mg, yield 74%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0050] The reaction steps and operations are the same as in Example 1, except that the solvent is water. The reaction was stopped, and the target product 1a (50.3 mg, yield 33%) was obtained after post-processing.

Embodiment 3

[0052] The reaction steps and operations are the same as in Example 1, except that the temperature is 80°C. The reaction was stopped, and the target product 1a (57.9 mg, yield 38%) was obtained after post-processing.

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Abstract

The invention discloses a cyclopropyl alkenyl amide derivative and a synthesizing method thereof. The method is characterized in that 1,1-dialkyl sulphanyl-1-alkenyl-3-cyclopropanone is utilized to synthesize 1-alkyl sulphanyl-1-amido-1-alkenyl-3-cyclopropanone, and then 1-alkyl sulphanyl-1-amido-1-alkenyl-3-cyclopropanone further reacts with iodosobenzene diacetate; 3-acetate, 1,3-carbonyl migration and 2,3-alkyl sulphanyl migration reaction are carried out to generate the cyclopropyl alkenyl amide derivative which can be further transformed to generate a functional product. The method has the advantages that the raw materials are easy to obtain; the operation is simple and convenient; the synthesizing reaction is mild in conditions; the efficiency is high; the substrate adaption is high; the product stereoselectivity is high; the functional group has diversity.

Description

technical field [0001] The invention relates to a cyclopropenamide derivative and a synthesis method thereof. Starting from 1,1-dialkylthio-1-ene-3-cyclopropanone, synthesis of 1-alkylthio-1-amino-1-ene-3-cyclopropanone, and then 1-alkylthio-1- Amino-1-ene-3-cyclopropanone reacts with iodobenzene acetate to generate cyclopropylacrylamide derivatives through 3-position acetate, 1,3-carbonyl transfer and 2,3-alkylthio transfer reaction . [0002] Compared with the reported synthesis method of cyclopropenyl acrylamide derivatives, the present invention has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions, high efficiency, and the product has good functional group diversity. The alkylthio group and the acetate group in the cyclopropenyl acrylamide structure synthesized by the invention are groups that can be further functionalized, and can be used as intermediates in the structure of medicines and chemical products. Background technique [00...

Claims

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Application Information

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IPC IPC(8): C07B45/06C07C319/14C07C323/60C07C253/00C07C255/31C07D307/54
CPCC07B45/06C07C253/00C07C319/14C07D307/54C07C323/60C07C255/31
Inventor 余正坤柳竹青
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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