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2-Alkylthioenamide derivatives and synthetic method thereof

A technology of alkylthioenamide and alkylthio, which is applied in the field of α, β-unsaturated amide compound 2-alkylthioenamide derivatives and its synthesis, which can solve the problem of weak atom economy, numerous preparation steps, Raw materials need to be activated, etc., to achieve good stereoselectivity and functional group diversity, easy to obtain raw materials, and mild conditions

Active Publication Date: 2017-12-19
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

There are two traditional synthesis methods of amides, one is the condensation reaction of carboxylic acid and its derivatives with amines, the other is the carbon-hydrogen activation of aldehydes and amines or their derivatives with strong affinity to construct amides bonds, most of them have many preparation 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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  • 2-Alkylthioenamide derivatives and synthetic method thereof
  • 2-Alkylthioenamide derivatives and synthetic method thereof
  • 2-Alkylthioenamide derivatives and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Weigh 1-thiomethyl-1-benzyl-1-en-3-one 2a (0.5mmol) and iodobenzene acetate (0.75mmol) in a 25mL Schlenk reaction flask, add DCE solvent 5mL under air, at 25 The reaction was stirred at °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 (130 mg, yield 76%). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0043] 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 (40 mg, yield 23%) was obtained after post-processing.

Embodiment 3

[0045]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 (99 mg, yield 58%) was obtained after post-treatment.

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Abstract

The invention discloses a 2-alkylthioenamide derivative and a synthesis method thereof. Using 1-alkylthio-1-amino-1-en-3-one and iodobenzene acetate as starting materials, under solvent-free or solvent-free milling conditions, through 3-position acetic acidification, 1,3 ‑Carbonyl migration and 2,3‑alkylthio group migration react to generate 2‑alkylthioenamide derivatives in one step, and the resulting amide derivatives can be further transformed into functionalized products. The method has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions, high efficiency, wide substrate adaptability, good stereoselectivity of products, and diverse functional groups.

Description

technical field [0001] The invention relates to an α, β-unsaturated amide compound 2-alkylthioenamide derivative and a synthesis method thereof. Using 1-alkylthio-1-amino-1-en-3-one and iodobenzene acetate as starting materials, under solvent-free or solvent-free milling conditions, through 3-acetate, 1,3- Carbonyl transfer and 2,3-alkylthio transfer reaction to generate 2-alkylthioenamide derivatives in one step. [0002] Compared with the reported synthesis method of amide derivatives, the present invention has easy-to-obtain raw materials, simple operation, mild synthesis reaction conditions, high efficiency, and the product has good stereoselectivity and functional group diversity. In the 2-alkylthioenamide structure synthesized by the invention, the 2-position alkylthio group and the 3-position acetate group are all groups that can be further functionalized, and can be used as intermediates in the structure of medicines and chemical products. Background technique [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/20C07C323/56C07C323/54C07D307/54C07D333/24
Inventor 余正坤黄菲
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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