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A kind of spiro-oxindole cyclopentane and β-lactone compound synthetic method

A spiro-oxindole cyclopentane and a synthesis method technology, which is applied in the field of synthesis of spiro-oxindole compounds, can solve problems such as difficulty in obtaining, and achieve simple operation, excellent diastereoselectivity, and high yield Effect

Active Publication Date: 2019-05-28
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the prior art, the synthesis method of spiro-oxindole derivatives is relatively common, but the synthesis method of spiro-oxindole cyclopentane β-lactone compound has not been reported, because the stable cyclopentane β-lactone The lipid product is difficult to obtain, and the four-membered ring lactone is easy to open the ring to obtain the cyclopentene product after decarboxylation

Method used

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  • A kind of spiro-oxindole cyclopentane and β-lactone compound synthetic method
  • A kind of spiro-oxindole cyclopentane and β-lactone compound synthetic method
  • A kind of spiro-oxindole cyclopentane and β-lactone compound synthetic method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] The chemical structural formula of nitrogen heterocyclic carbene is as follows:

[0031]

[0032] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, 1a (19.8 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence, and add 0.5 mL of Toluene was reacted at 0°C for 24 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:5) to obtain the target product 3a (21.1 mg) as a white solid. The rate was 54%, >99 / 1 dr, 91% ee; antibacterial drugs could be prepared.

[0033] Add nitrogen heterocyclic carbene (1.85 mg, 0.005 mmol) as a catalyst, and 1a (19.8 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (5 mg) in turn into the reaction flask, add 0.5 mL mesitylene , reacted at 0°C for 24 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:5) to obtain the target product 3a (15.2 mg), white so...

Embodiment 2

[0037]

[0038] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, 1b (24.3 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence, and add 0.5 mL of Toluene was reacted at 0°C for 24 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:5) to obtain the target product 3b (23.9 mg) as a white solid. The rate was 57%, >99 / 1 dr, 91% ee, and antineoplastic drugs could be prepared.

[0039] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1b (24.3 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol) in sequence in the reaction flask, add 0.5 mL of mesitylene, at 0 °C After 24 hours of reaction, the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:5) to obtain the target product 3b (20.8 mg), a white solid, with a yield of 51%, >99 / 1 dr, 88% ee.

[0040] The product 3b was analyzed and the results are as foll...

Embodiment 3

[0042]

[0043] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1b (26.5 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence in the reaction flask, add 0.5 mL of Toluene was reacted at 0°C for 24 hours. The reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 3c (28.3 mg) as a white solid. The rate was 65%, >99 / 1 dr, 86% ee, and enzyme inhibitors could be prepared.

[0044] Add nitrogen heterocyclic carbene (3.7 mg, 0.01 mmol) as a catalyst, and 1b (26.5 mg, 0.15 mmol), 2a (26 mg, 0.1 mmol), 4Å molecular sieves (10 mg) in sequence in the reaction flask, add 0.5 mL tetrahydrofuran, After reacting at 0°C for 24 hours, the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 3c (20.6mg), a white solid, and the yield was 47%, >99 / 1 dr, 81% ee.

[0045] The produc...

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Abstract

The invention discloses a method for synthesizing a spiro-oxindole cyclopentane-β-lactone compound. Specifically, phenyl unsaturated aldehydes and unsaturated ketoesters are used as reactants, nitrogen-heterocyclic carbene is used as a catalyst, and the reaction to obtain the spiro-oxindole cyclopentane β ‑ Lactone compounds. The method disclosed by the invention has simple and easy raw materials, mild reaction conditions, simple and convenient post-treatment, wide range of applicable substrates, high yield, high diastereoselectivity and enantioselectivity; the product synthesized thereby can be used for Intermediates in the synthesis of drugs and pesticides.

Description

technical field [0001] The invention relates to the synthesis of spiro-oxindole compounds, in particular to a catalytic synthesis method of spiro-oxindole cyclopentane and β-lactone compounds. Background technique [0002] Spiral oxindole compounds widely exist in natural products, and have significant physiological and pharmacological activities such as antiviral, bactericidal, enzyme activity inhibitory, antioxidative, antiradiative, and antitumor. At the same time, it is also an indispensable and important structural unit in many drug molecules, so it has attracted the attention of many scientists. The cyclopentane β-lactone compound also has good biological activity and medicinal value, but it is difficult to obtain because the product is prone to decarboxylation and leaves a molecule of carbon dioxide. Therefore, the development of efficient methods to combine these two types of structures with biological activity and pharmacological effects to synthesize chiral spiro-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107B01J31/02A61P31/00A61P35/00A61P31/18A61P31/12
CPCB01J31/0271C07D491/107
Inventor 王兴旺张俊琦
Owner SUZHOU UNIV
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