A kind of synthetic method of chiral quaternary oxazolinone compound

A carboxazolone and synthesis method technology, applied in the field of catalytic synthesis of chiral quaternary carboxazolone compounds, can solve the problems of low stereoselectivity, limited range of substrates, complex catalysts, etc., and achieve three-dimensional Good selectivity, excellent corresponding selectivity, and easy purification effect

Inactive Publication Date: 2016-08-24
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Existing methods for synthesizing chiral quaternary oxazolinone compounds have the disadvantages of low stereoselectivity, complex catalysts, low selectivity, and a wide range of substrates; and pure chiral compounds are rare in nature, so preparation and use A chiral compound with a single configuration can avoid the side effects of another configuration in product use, so the development and utilization of chiral compounds is more important

Method used

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  • A kind of synthetic method of chiral quaternary oxazolinone compound
  • A kind of synthetic method of chiral quaternary oxazolinone compound
  • A kind of synthetic method of chiral quaternary oxazolinone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Chiral quinine thiourea (2.8 mg, 0.005 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4Å molecular sieves (150 mg) were added to the reaction flask in sequence, and 1.5 mL of m-xylene was added , reacted at minus 30 degrees Celsius for 12 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5a (5 mg), a white solid, and the yield 10%, >20 / 1 dr, 30% ee.

[0029] Chiral quinine thiourea (5.6 mg, 0.01 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4Å molecular sieves (150 mg) were added to the reaction flask in sequence, and 1.5 mL of m-xylene was added , and reacted at minus 30 degrees Celsius for 12 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5a (27.2mg), a white solid, and The rate was 55%, >20 / 1 dr, 70% ee.

[0030] Chiral quinine thiourea (1...

Embodiment 2

[0033]

[0034] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7mg, 0.1mmol), 3a (47.4mg, 0.2 mmol), 4Å molecular sieves (150mg) were added to the reaction flask in sequence, and 1.5mL m-xylene was added , and reacted at minus 30 degrees Celsius for 12 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5b (40.0mg), a white solid, and The rate was 78%, >20 / 1 dr, 91% ee.

[0035] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7mg, 0.1mmol), 3a (35.5mg, 0.15 mmol), 4Å molecular sieves (150mg) were added to the reaction flask in sequence, and 1.5mL m-xylene was added , and reacted at minus 30 degrees Celsius for 12 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5b (30.8mg), a white solid, and The rate was 60%, >20 / 1 dr, 91% ee.

[0036]Chiral quinine thiourea (11.2 mg, 0....

Embodiment 3

[0039]

[0040] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2c (33.8 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4Å molecular sieves (150 mg) were added to the reaction flask in sequence, and 1.5 mL of m-xylene was added , reacted at minus 30 degrees Celsius for 12 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5c (56.2 mg), a white solid, yield The rate was 98%, >20 / 1 dr, 94% ee.

[0041] Add chiral quinine thiourea (11.2 mg, 0.02 mmol), and 2c (33.8 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol) sequentially into the reaction flask, add 1.5 mL m-xylene, and store at minus 30 degrees Celsius After 12 hours of reaction, the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether = 1:10) to obtain the target product 5c (40.1 mg), a white solid, with a yield of 70%,> 20 / 1 dr, 94% ee.

[0042] The product 5c was analyzed and the results are...

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Abstract

The invention discloses a synthetic method for a chiral quaternary carbon oxazolidinone compound. The synthetic method comprises the following steps: taking o-hydroxy chalcone and azlactone as reactants and synthesizing in a solvent under the catalysis of chiral multifunctional chiral quinine thiourea to obtain a product. The synthetic method disclosed by the invention has the advantages that raw materials are easy to obtain, the reaction conditions are mild, the post-treatment is simple and convenient, the applicable substrate scope is wide, the yield is high, and the enantioselectivity is high; the product obtained by the synthesis method can be used for synthesizing an intermediate of a drug and a pesticide.

Description

technical field [0001] The invention relates to the synthesis of chiral quaternary carbon compounds, in particular to a catalytic synthesis method of chiral quaternary carbon oxazolone compounds. Background technique [0002] Chiral quaternary carbon compounds have a wide range of biological activities such as anti-tumor, anti-plant virus, plant growth regulation, weeding, sterilization, inhibition of enzyme activity, anti-oxidation and radiation protection, and destruction of biological cell membranes, and have attracted the attention of many scientists. Chiral quaternary carbon oxazolinone compounds, as chiral quaternary carbon compounds, also have similar potential application value, so choosing an efficient method to synthesize chiral quaternary carbon oxazolinone compounds has attracted great interest from many chemists. Recently, many synthetic methods have emerged. [0003] In the field of organic synthesis, the reaction catalyzed by asymmetric small molecules has be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/42C07D413/06
CPCC07D263/42C07D413/06
Inventor 王兴旺张绍云
Owner SUZHOU UNIV
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