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Polysubstituted beta-lactam compound and preparation method thereof

A technology for lactams and compounds, which is applied in the field of multi-substituted β-lactam compounds and their preparation, can solve problems such as complex starting materials, and achieve the effects of simple raw materials and reagents, good functional group diversity, and mild reaction conditions

Pending Publication Date: 2021-12-17
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of reaction has been rarely studied and often requires complex starting materials

Method used

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  • Polysubstituted beta-lactam compound and preparation method thereof
  • Polysubstituted beta-lactam compound and preparation method thereof
  • Polysubstituted beta-lactam compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] A multi-substituted β-lactam compound has the structures shown in the following formulas I-1 and I-2, and the reaction route is as follows:

[0047]

[0048] The specific preparation method is as follows:

[0049] N 2 Under atmosphere, add 26.4mg (0.2mmol) compound Ⅳ-1, 58.8mg (0.3mmol) compound Ⅴ-1, 45.3mg (0.3mmol) compound Ⅵ-1, 7.5mg (0.02mmol) six Copper(I) tetraethylcyanide fluorophosphate, 13.8mg (0.02mmol) chiral ligand L, 27.6mg (0.2mmol) potassium carbonate, and finally 1mL of dry acetonitrile was added, and the resulting mixture was stirred and reacted at 0°C for 18 hours; the resulting reaction After the mixture was raised to room temperature, it was filtered with diatomaceous earth, and the filtrate was evaporated to remove the solvent to obtain a crude product, which was separated by silica gel column chromatography, and the eluent was a mixed solution of ethyl acetate and petroleum ether. The volume ratio is 2:1~5:1, and a pair of diastereoisomers, na...

Embodiment 2

[0063] A multi-substituted β-lactam compound has the structures shown in the following formulas I-3 and I-4, and the reaction route is as follows:

[0064]

[0065] The specific preparation method is as follows:

[0066] N 2 Under atmosphere, add 26.4mg (0.2mmol) compound IV-1, 69.5mg (0.3mmol) compound V-2, 45.3mg (0.3mmol) compound VI-1, 7.5mg (0.02mmol) six Copper(I) tetraethylcyanide fluorophosphate, 13.8mg (0.02mmol) chiral ligand L, 27.6mg (0.2mmol) potassium carbonate, and finally 1mL of dry acetonitrile was added, and the resulting mixture was stirred and reacted at 0°C for 18 hours; the resulting reaction After the mixture was raised to room temperature, it was filtered with diatomaceous earth, and the filtrate was evaporated to remove the solvent to obtain a crude product, which was separated by silica gel column chromatography, and the eluent was a mixed solution of ethyl acetate and petroleum ether. The volume ratio was 2:1-5:1, and a pair of diastereoisomers,...

Embodiment 3

[0075] A multi-substituted β-lactam compound has the structures shown in the following formulas I-5 and I-6, and the reaction route is as follows:

[0076]

[0077] The specific preparation method is as follows:

[0078] N 2 Under atmosphere, add 26.4mg (0.2mmol) compound IV-1, 63.4mg (0.3mmol) compound V-3, 45.3mg (0.3mmol) compound VI-1, 7.5mg (0.02mmol) six Copper(I) tetraethylcyanide fluorophosphate, 13.8mg (0.02mmol) chiral ligand L, 27.6mg (0.2mmol) potassium carbonate, and finally 1mL of dry acetonitrile was added, and the resulting mixture was stirred and reacted at 0°C for 18 hours; the resulting reaction After the mixture was raised to room temperature, it was filtered with diatomaceous earth, and the filtrate was evaporated to remove the solvent to obtain a crude product, which was separated by silica gel column chromatography, and the eluent was a mixed solution of ethyl acetate and petroleum ether. The volume ratio was 2:1-5:1, and a pair of diastereoisomers,...

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Abstract

The invention provides a polysubstituted beta-lactam compound and a preparation method thereof. The polysubstituted beta-lactam compound has a structure as shown in a general formula I, II or III. The invention also provides a preparation method of the polysubstituted beta-lactam compound, which comprises the following steps: in a solvent A, under the catalysis of a copper catalyst and a chiral ligand and the existence of alkali, carrying out copper-catalyzed Kinugasa interruption reaction on a phenylacetylene compound, a nitrone compound and a third component compound to obtain the polysubstituted beta-lactam compound; according to the invention, a Kinugasa reaction and a subsequent functionalization reaction are connected in series through a one-pot method, protonation of a traditional Kinugasa reaction enolated copper intermediate is blocked through a third component, and multiple highly-functionalized polysubstituted beta-lactam compounds are synthesized. The method provided by the invention has the advantages of simple initial raw materials, mild reaction conditions and excellent yield and enantioselectivity.

Description

technical field [0001] The invention relates to a multi-substituted β-lactam compound and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] β-lactam is a very important heterocyclic skeleton in organic compounds, and has a wide range of applications in the fields of medicine, biochemistry and material chemistry. β-lactam skeletons are widely found in many clinically used antibiotics, such as penicillins and cephalosporins, and some drugs with β-lactam skeletons also exhibit important antifungal and anti-inflammatory activities, and can even be used as cholesterol-lowering drugs . [0003] β-lactam is a heavyweight heterocyclic skeleton, and its synthesis method has also been extensively studied. There are many methods for the synthesis of β-lactams, one of which is the Kinugasa reaction, which was first reported by Kinugasa in 1972. It can be used to synthesize β-lactam compounds. The traditional Kinugasa rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D205/08
CPCC07D205/08
Inventor 徐政虎齐佳霖
Owner SHANDONG UNIV
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