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Preparation method of 1, 3-diarylpropargyl ketone

A technology for diarylpropynone and alkynoic acid, which is applied in the field of preparation of 1,3-diarylpropynone and achieves the effects of good compatibility, mild reaction conditions and simple catalytic system

Inactive Publication Date: 2018-07-13
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While alkynyl carboxylic acid is used as a source of alkyne through decarboxylation process, it also has the advantages of good stability, easy storage and handling, etc. However, silver-catalyzed decarboxylation of alkynyl carboxylic acid is still very challenging.

Method used

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  • Preparation method of 1, 3-diarylpropargyl ketone
  • Preparation method of 1, 3-diarylpropargyl ketone
  • Preparation method of 1, 3-diarylpropargyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～14

[0033] The α-keto acid (1.1mmol, R 1 =H), aryl alkynoic acid (1mmol, R 2=H), silver catalyst (5mol%) and oxidizing agent (2mmol) were dispersed in the solvent, and then stirred at 50° C. for 3 hours under air atmosphere. After the reaction, with Et 2 O (5 mL) was extracted three times, and the combined organic phases were concentrated under reduced pressure. The obtained crude product was subjected to column chromatography (300-400 mesh silica gel, petroleum ether and ethyl acetate as eluents) to obtain the target product. The silver catalyst, oxidant and solvent used and the reaction results are shown in Table 1.

[0034] The reaction condition and reaction result of table 1 embodiment 1~10

[0035]

[0036]

[0037] a The total volume of solvent was kept at 2 mL.

Embodiment 14～29

[0039] α-keto acid (1.1mmol), aryl alkynoic acid (1mmol, R 2 =H), AgOAc (5mol%) and (NH 4 ) 2 S 2 o 8 (2mmol) dispersed in DMSO (1mL) and H 2 O (1 mL) in a mixed solvent, and then stirred at 50° C. for 3 hours under air atmosphere. After the reaction, with Et 2 O (5 mL) was extracted three times, and the combined organic phases were concentrated under reduced pressure. The obtained crude product was subjected to column chromatography (300-400 mesh silica gel, petroleum ether and ethyl acetate as eluents) to obtain the target product. The substrates used and the reaction results are listed in Table 2.

[0040] The reaction substrate and result used in table 2 embodiment 14~29

[0041]

Embodiment 30～41

[0043] The α-keto acid (1.1mmol, R 1 =H), aryl alkynoic acid (1mmol, R 2 =H), AgOAc (5mol%) and (NH 4 ) 2 S 2 o 8 (2mmol) dispersed in DMSO (1mL) and H 2 O (1 mL) in a mixed solvent, and then stirred at 50° C. for 3 hours under air atmosphere. After the reaction, with Et 2 O (5 mL) was extracted three times, and the combined organic phases were concentrated under reduced pressure. The obtained crude product was subjected to column chromatography (300-400 mesh silica gel, petroleum ether and ethyl acetate as eluents) to obtain the target product. The substrates used and the reaction results are listed in Table 3.

[0044] The reaction substrate and result used in table 3 embodiment 30~41

[0045]

[0046] The characterization data of some products are as follows:

[0047] 1,3-Diphenylprop-2-yn-1-one:White solid. 1 H NMR (400MHz, CDCl 3 )δ8.08(d, J=7.2Hz, 2H), 7.54(d, J=6.8Hz, 2H), 7.50–7.44(m, 1H), 7.38(t, J=7.6Hz, 2H), 7.32( d,J=7.2Hz,1H),7.28–7.26(m,2H). 13 C...

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Abstract

The invention discloses a preparation method of 1, 3-diarylpropargyl ketone. The preparation method, comprises the following steps: under the action of a silver catalyst and an oxidant, performing a decarboxylating coupling reaction on alpha-ketonic acid and aryl acetylenic acid in a solvent, and after completion of the reaction, posttreating to obtain the 1, 3- diarylpropargyl ketone. By the preparation method, reagents are cheap and easy to obtain, the reaction condition is mild, reactive functional groups are good in compatibility, the catalyst is cheap and easy to obtain, and a catalysis system is simple.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 1,3-diaryl propynyl ketone. Background technique [0002] 1,3-Diarylpropynyl ketones have attracted much attention from chemists due to their multifunctional properties in biomedicine and materials, as well as their wide application in the synthesis of bioactive products. In the synthesis of natural products, 1,3-diarylpropynyl ketones can be used as precursors to construct various heterocyclic structural units, and a variety of furans, flavones, benzodiazepines, pyrroles, pyrazoles, pyrimidines, and quinolones have been synthesized. Heterocyclic derivatives, and used in the synthesis of natural products with different pharmacological properties. Due to its unique structural characteristics and biological activity, the synthetic strategy of 1,3-diarylpropynyl ketone has become the research focus of organic chemists, and its synthetic methods a...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C49/796C07C49/813C07C69/76C07C255/56C07C205/45C07C45/68C07C67/343C07C201/12C07C253/30C07D215/14C07B37/04C07C49/798C07D333/22
CPCC07B37/04C07C45/68C07C67/343C07C201/12C07C253/30C07D215/14C07D333/22C07C49/84C07C49/796C07C49/813C07C69/76C07C255/56C07C205/45C07C49/798
Inventor 程凯
Owner SHAOXING UNIVERSITY
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