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Polysubstituted ketene imine and synthesis method thereof

A ketene imine and multi-substitution technology, which is applied in the field of multi-substituted ketene imine and its synthesis, can solve the problems of expensive catalyst, long reaction time, and low yield, and achieve good atom economy and short reaction time , the effect of easy operation

Active Publication Date: 2019-12-20
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In the above several methods for selectively constructing multi-substituted ketene imines, the catalyst is expensive, the reaction time is long, and the yield is low.

Method used

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  • Polysubstituted ketene imine and synthesis method thereof
  • Polysubstituted ketene imine and synthesis method thereof
  • Polysubstituted ketene imine and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Add 3 mL of tetrahydrofuran into a 25 mL pressure-resistant sealed tube as a solvent, then add enynone (0.5 mmol), 4-bromo-2,6-dimethylphenylisonitrile (0.5 mmol) of the two reactants and catalyst tetrakis(triphenylphosphine) palladium (0.1 mmol), the pressure-resistant tube was sealed, and reacted at room temperature, followed by detection by TLC until the end of the reaction. The reaction system was rotary evaporated under vacuum to obtain a concentrate, which was separated by column chromatography (eluent: PE:EA =50:1) to obtain the target product 3a (188 mg, 89% yield).

[0033] The structural formula of compound 3a is:

[0034]

[0035] Molecular formula: C 23 h 20 BrNO 2

[0036] Chinese name: 1-(5-(2-((4-bromo-2,6-dimethylphenyl)imino)-1-phenylethenyl)-2-methylfuran-3-yl)ethyl ketone

[0037] English name:

[0038] 1-(5-(2-((4-bromo-2,6-dimethylphenyl)imino)-1-phenylvinyl)-2-methylfuran-3-yl)ethanone

[0039] Molecular weight: 421.0677

[0...

Embodiment 2

[0045] Example 2: Add 3 mL of tetrahydrofuran into a 25 mL pressure-resistant sealed tube as a solvent, then add enynone (0.5 mmol), 4-bromo-2,6-dimethylphenylisonitrile (0.5 mmol) of the two reactants and catalyst tetrakis(triphenylphosphine) palladium (0.1 mmol), the pressure-resistant tube was sealed, and reacted at room temperature, followed by detection by TLC until the end of the reaction. The reaction system was rotary evaporated under vacuum to obtain a concentrate, which was separated by column chromatography (eluent: PE:EA =50:1) to obtain the target product 3b (123 mg, 49% yield).

[0046] The structural formula of compound 3b is:

[0047]

[0048] Molecular formula: C 23 h 18 Br 2 NO 2

[0049] Chinese name: 1-(5-(2-((4-bromo-2,6-dimethylphenyl)imino)-1-(4-bromophenyl)vinyl)-2-methylfuran- 3-yl)ethanone

[0050] English name:

[0051] 1-(5-(2-((4-bromo-2,6-dimethylphenyl)imino)-1-(4-bromophenyl)vinyl)-2-methylfuran-3-yl)ethanone

[0052] Molecular weig...

Embodiment 3

[0059] Example 3: Add 3 mL of tetrahydrofuran to a 25 mL pressure-resistant sealed tube as a solvent, then add enynone (0.5 mmol), 4-bromo-2,6-dimethylphenylisonitrile (0.5 mmol) of the two reactants and catalyst tetrakis(triphenylphosphine) palladium (0.1 mmol), the pressure-resistant tube was sealed, and reacted at room temperature, followed by detection by TLC until the end of the reaction. The reaction system was rotary evaporated under vacuum to obtain a concentrate, which was separated by column chromatography (eluent: PE:EA =50:1) to obtain the target product 3c (176 mg, 72% yield).

[0060] The structural formula of compound 3c is:

[0061]

[0062] Molecular formula: C 24 h 19 BrF 3 NO 2

[0063] Chinese name: 1-(5-(2-((4-bromo-2,6-dimethylphenyl)imino)-1-(4-(trifluoromethyl)phenyl)vinyl)-2 -Methylfuran-3-yl)ethanone

[0064] English name: 1-(5-(2-((4-bromo-2,6-dimethylphenyl)imino)-1-(4-(trifluoromethyl)phenyl)vinyl)-2-methylfuran-3-yl)ethanone

[0065] Mo...

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Abstract

The invention relates to polysubstituted ketene imine and a synthesis method thereof. The structure of the compound is shown in the specification. According to the invention, 4-bromo-2,6-dimethylphenyl isonitrile and eneyne ketone are subjected to an insertion reaction, and in the reaction, palladium activates alkynyl triple bonds, so that intramolecular nucleophilic attack of carbonyl oxygen is promoted; and then an active resonance stabilizer is generated throughcyclization, and the active resonance stabilizer and isonitrile are subjected to an insertion reaction under the mechanism, so thatthe polysubstituted ketene imine with a relatively complex structure is synthesized. The reaction conditions are mild, the reaction time is short, operation is simple and convenient, and atom economyis good. The method provides a new synthetic route for synthesis of complex polysubstituted ketene imine, and has a potential application value in organic synthesis.

Description

technical field [0001] The invention relates to a polysubstituted ketene imine and a synthesis method thereof. Background technique [0002] Polysubstituted keteneimines are compounds with allene-like structures, which exhibit high reactivity in nucleophilic addition reactions, cycloaddition reactions, free radical reactions, migratory rearrangement reactions, and other reactions. Therefore, multi-substituted keteneimines are a very important class of compounds and reaction intermediates in organic synthesis. They have important applications in the synthesis of heterocyclic compounds and the total synthesis of natural products. For example, some multi-substituted keteneimine structures are Used in the total synthesis of drug molecule (S)-Verapamil. [0003] Multi-substituted keteneimines have important research and application value, and people have been working on a simple method for synthesizing keteneimine skeleton compounds. In recent years, the methods for constructin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
CPCC07D307/46
Inventor 李健黄洁李峰崔雷贾学顺
Owner SHANGHAI UNIV