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Spiro oxindole imidazolinyl oxazepine compound and synthesis method thereof

A technology of spirocyclic oxindole imidazoline and oxazepine, which is applied in the field of synthesis of spirocyclic oxindole imidazoline compounds and achieves excellent diastereoselectivity, high yield and good chemoselectivity Effect

Active Publication Date: 2015-12-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the field of organic synthesis research, Lewis acid and Bronsted acid catalysis can be applied to the synthesis of many organic compounds; however, it is possible to efficiently synthesize spiro-oxindole imidazoline and oxazepine structures through Lewis acid catalysis or Bronsted acid catalysis The compound has not been reported in the literature

Method used

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  • Spiro oxindole imidazolinyl oxazepine compound and synthesis method thereof
  • Spiro oxindole imidazolinyl oxazepine compound and synthesis method thereof
  • Spiro oxindole imidazolinyl oxazepine compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add p-toluenesulfonic acid monohydrate (0.95mg, 0.005mmol) and 1a (43.1 mg, 0.22 mmol), 2a (15.9mg, 0.1mmol), add 2mL tetrahydrofuran, stir and react at room temperature for 24 hours, the reaction system can be obtained by simple column chromatography (dichloromethane:petroleum ether=2:1) ​​to obtain the target product 3a (Yield: 27.6mg, 53%), white solid, diastereoselectivity>99 / 1.

[0033] Add iron (II) trifluoromethanesulfonate (1.8 mg, 0.005 mmol) and 1a (43.1 mg, 0.22 mmol), 2a (15.9mg, 0.1mmol), add 2mL tetrahydrofuran, stir and react at room temperature for 24 hours, the reaction system can be obtained by simple column chromatography (dichloromethane:petroleum ether=2:1) ​​to obtain the target product 3a (Yield 21.3 mg, 41% yield), white solid, diastereoselectivity >99 / 1.

[0034] P-toluenesulfonic acid monohydrate (1.9mg, 0.01mmol) or iron (II) trifluoromethanesulfonate (3.5mg, 0.01mmol) was added sequentially into the reaction flask as a catalys...

Embodiment 2

[0038]

[0039] Add p-toluenesulfonic acid monohydrate (1.9mg, 0.01mmol) to the reaction flask successively, 1a (43.1 mg, 0.22 mmol), 2b (15.9mg, 0.1mmol), add 2mL tetrahydrofuran, stir and react at room temperature for 24 hours, the reaction system can be obtained by simple column chromatography (dichloromethane:petroleum ether=1:1) to obtain the target product 3a (48.4 mg, 93% yield), white solid, diastereoselectivity >99 / 1.

[0040] Iron (II) trifluoromethanesulfonate (3.5 mg, 0.01 mmol) was successively added into the reaction flask, 1a (43.1 mg, 0.22 mmol), 2b (15.9mg, 0.1mmol), add 2mL tetrahydrofuran, stir and react at room temperature for 24 hours, the reaction system can be obtained by simple column chromatography (dichloromethane:petroleum ether=1:1) to obtain the target product 3a (45.8 mg yield, 88% yield), white solid, diastereoselectivity >99 / 1.

[0041] to product 3b After analysis, the results are as follows: 1 HNMR (400MHz, CDCl3) δ7.42 (dd, J =7.2,0...

Embodiment 3

[0043]

[0044] Add p-toluenesulfonic acid monohydrate (1.9mg, 0.01mmol) to the reaction flask successively, 1a (43.1 mg, 0.22 mmol), 2c (24.9mg, 0.1mmol), add 2mL diethyl ether, stir and react at room temperature for 24 hours, the reaction system can be obtained by simple column chromatography (eluent: dichloromethane:petroleum ether=1:1) to obtain the target product 3c (Yield: 47.9 mg, 92%), white solid, diastereoselectivity >99 / 1.

[0045] Iron (II) trifluoromethanesulfonate (3.5 mg, 0.01 mmol) was successively added into the reaction flask, 1a (43.1 mg, 0.22 mmol), 2c (24.9mg, 0.1mmol), add 2mL tetrahydrofuran, stir and react at room temperature for 24 hours, the reaction system can be obtained by simple column chromatography (dichloromethane: petroleum ether = 1:1 as the eluent) to obtain the target product 3c (Yield: 46.3 mg, 89%), white solid, diastereoselectivity >99 / 1.

[0046] to product 3c After analysis, the results are as follows: 1 HNMR (400MHz, CDCl 3 ...

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Abstract

The present invention discloses a spiro oxindole imidazolinyl oxazepine compound and a synthesis method thereof, wherein particularly diazo oxindole and dibenzoxazepine are adopted as reactants, and synthesis is performed in a solvent under catalysis of iron trifluomethanesulfonate (II) or a p-toluenesulfonic acid monohydrate to obtain the product. According to the present invention, the method has characteristics of simple and easily-available raw materials, mild reaction conditions, simple and convenient post-treatment, wide substrate application range, high yield and high diastereoselectivity; and the synthesized product can be used for synthesizing the intermediate of drugs and insecticides.

Description

technical field [0001] The invention relates to the synthesis of spiro-ring oxindole imidazoline compounds, in particular to a spiro-ring oxindole imidazolinoxazepine compound and a catalytic synthesis method thereof. Background technique [0002] Spiro-oxindole imidazoline compounds widely exist in natural products, and have significant physiological and pharmacological activities, such as anti-virus, bactericidal, anti-enzyme activity, anti-tumor and other biological activities, and widely exist in alkaloids middle. At the same time, it is also an indispensable and important structural unit in many drug molecules, and has attracted the attention of many scientists. Dibenzoxazepines also have good biological activity and medicinal value, and are commonly found in alkaloids and antidepressant drugs. For example, the commonly used antidepressant drug amoxapine has good clinical drug effect (Formula 1). In the prior art, there is no report on the synthesis method of spiro-o...

Claims

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Application Information

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IPC IPC(8): C07D498/22
CPCC07D498/22
Inventor 王兴旺张俊琦
Owner SUZHOU UNIV
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