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Method for producing tetra-substituted vinyl 2,4-oxazolidinedione from carbon dioxide

A technology of vinyl oxazolidine and carbon dioxide, which is applied in the field of preparation of tetrasubstituted vinyl oxazolidine-2,4-dione, and functionalization reaction, which can solve the problems of expensive and difficult-to-obtain substrates, and achieve the extension of product types , mild reaction conditions and wide applicability

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

AI Technical Summary

Problems solved by technology

[0005] In summary, in the existing synthetic methods of tetrasubstituted vinyl oxazolidine-2,4-dione compounds, there are many shortcomings that need to be overcome, such as: expensive substrates, not easy to obtain, etc. Therefore, further development of four A green, efficient, and inexpensive synthetic method for substituted vinyloxazolidine-2,4-dione, which not only has high scientific research value, but also has broad application prospects

Method used

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  • Method for producing tetra-substituted vinyl 2,4-oxazolidinedione from carbon dioxide
  • Method for producing tetra-substituted vinyl 2,4-oxazolidinedione from carbon dioxide
  • Method for producing tetra-substituted vinyl 2,4-oxazolidinedione from carbon dioxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 3-benzyl-5-(dibenzylidene)oxazolidine-2,4-dione

[0026] [3-benzyl-5-(diphenylmethylene)oxazolidine-2,4-dione]

[0027]

[0028] In the dried Schlenk tube, add in sequence: N-benzyl-3-phenylpropanamide (0.2mmol, 47mg), potassium carbonate (0.4mmol, 55.2mg), iodobenzene (0.24mmol, 49mg) , bistriphenylphosphine palladium dichloride (0.02mmol, 14mg), cuprous iodide (0.03mmol, 6mg), dimethyl sulfoxide 2mL, with CO 2 Replace the gas in the reaction tube three times, and finally fill the reaction tube with 0.1MPa CO 2 , and the above-mentioned Schlenk tube was placed at ambient temperature and stirred for 24 h. The reaction was terminated, and the reaction solution was quenched with 2 mL of saturated brine, extracted several times with ethyl acetate (4 mL×5), the organic phases were combined, and the solvent was removed on a rotary evaporator. Finally, it was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether ...

Embodiment 2

[0030] Example 2: Preparation of 3-benzyl-5-(dibenzylidene)oxazolidine-2,4-dione

[0031] [3-benzyl-5-(diphenylmethylene)oxazolidine-2,4-dione]

[0032]

[0033] In the dried Schlenk tube, add in sequence: N-benzyl-3-phenylpropanamide (0.2mmol, 47mg), potassium carbonate (0.4mmol, 55.2mg), iodobenzene (0.24mmol, 49mg) , bistriphenylphosphine palladium dichloride (0.01mmol, 7mg), cuprous iodide (0.06mmol, 6mg), dimethyl sulfoxide 2mL, with CO 2 Replace the gas in the reaction tube three times, and finally fill the reaction tube with 0.1MPa CO 2 , and the above-mentioned Schlenk tube was placed at ambient temperature and stirred for 24 h. The reaction was terminated, and the reaction solution was quenched with 2 mL of saturated brine, extracted several times with ethyl acetate (4 mL×5), the organic phases were combined, and the solvent was removed on a rotary evaporator. Finally, it was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether =...

Embodiment 3

[0034] Example 3: Preparation of 3-benzyl-5-(dibenzylidene)oxazolidine-2,4-dione

[0035] [3-benzyl-5-(diphenylmethylene)oxazolidine-2,4-dione]

[0036]

[0037] In the dried Schlenk tube, add in sequence: N-benzyl-3-phenylpropanamide (0.2mmol, 47mg), potassium carbonate (0.4mmol, 55.2mg), iodobenzene (0.24mmol, 49mg) , bistriphenylphosphine palladium dichloride (0.015mmol, 10.5mg), cuprous iodide (0.05mmol, 9.5mg), dimethyl sulfoxide 2mL, with CO 2 Replace the gas in the reaction tube three times, and finally fill the reaction tube with 0.1MPa CO 2 , and the above-mentioned Schlenk tube was placed at ambient temperature and stirred for 24 h. The reaction was terminated, and the reaction solution was quenched with 2 mL of saturated brine, extracted several times with ethyl acetate (4 mL×5), the organic phases were combined, and the solvent was removed on a rotary evaporator. Finally, it was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum e...

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PUM

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Abstract

The invention belongs to the technical field of fixation and conversion of carbon dioxide, particularly relates to a functionalization reaction of an alkynyl-containing compound, and discloses a method for producing tetra-substituted vinyl 2,4-oxazolidinedione from carbon dioxide. The method for producing the tetra-substituted vinyl 2,4-oxazolidinedione from the carbon dioxide comprises the specific technology steps: in a Schlenk tube subjected to dehydration and deoxidation, adding a catalyst, a copper salt, an alkali, propargylamide, halohydrocarbon, the carbon dioxide and a solvent according to a ratio, placing the Schlenk tube in an environment at environmental temperature, and conducting stirring for 16-24 hours; and finally, conducting silica gelcolumn chromatography to obtain the tetra-substituted vinyl 2,4-oxazolidinedione. According to the method for producing the tetra-substituted vinyl 2,4-oxazolidinedione from the carbon dioxide, the CO2 is adopted as a carboxyl source forthe first time, and at the environmental temperature, the tetra-substituted vinyl 2,4-oxazolidinedione is built.

Description

technical field [0001] The invention belongs to the technical field of carbon dioxide fixation conversion, and specifically relates to the functional group reaction of alkyne-containing compounds, in particular to a method for preparing tetrasubstituted vinyl oxazolidine-2,4-dione from carbon dioxide. Background technique [0002] Tetrasubstituted vinyloxazolidine-2,4-dione and its derivatives are an important class of structural units, which widely exist in a variety of biologically active natural products and pharmaceutical and pesticide molecules. For example: This structural unit is contained in some herbicides, antiepileptic drugs, anti-inflammatory drugs, and photosensitizing dyes. (See: (A) Pastore, V.; Sabatier, L.; Enrique, A.; Marder, M.; Bruno-Blanch, L.E. Bioorg. Med. Chem. 2013, 21, 841-846. (B) (a) Heerding , D.A.; Christmann, L.T.; Clark, T.J.; Holmes, D.J.; Rittenhouse, S.F.; , D.T.; Cetenko, W.A.; Sorenson, R.J.; Kostlan, C.R.; Sircar, J.C.; .1958,58,63-9...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/44C07D413/06
CPCC07D263/44C07D413/06Y02P20/584
Inventor 孙松周聪成江董亚群
Owner CHANGZHOU UNIV
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