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Polysubstituted isoxazolidine derivative and preparation method thereof

A technology for isoxazolidine and derivatives, which is applied in the field of polysubstituted isoxazolidine derivatives and their preparation, can solve the problems of large equipment requirements, harsh conditions and high energy consumption, and achieves simple method, mild conditions and high yield. high effect

Inactive Publication Date: 2017-11-21
QUZHOU YINGTE HIGH MOLECULAR MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are not many reports on the synthesis of multi-substituted isoxazolidine derivatives, and most of the existing synthesis methods use high-temperature heating systems, which consume high energy, require harsh conditions for equipment, and have low yields.

Method used

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  • Polysubstituted isoxazolidine derivative and preparation method thereof
  • Polysubstituted isoxazolidine derivative and preparation method thereof
  • Polysubstituted isoxazolidine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Into a 7mL round bottom flask, add 59mg (0.3mmol) diphenylnitrone, 53mg (0.45mmol) β-methylstyrene, 1.2mg (0.0075mmol) photocatalyst and 4mL dichloromethane, stir well and pass nitrogen After 30 minutes, it was placed under blue LEDs light, and reacted with light at room temperature for 12 hours. After the reaction was completed, the reaction solvent was concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether: ethyl acetate with a volume ratio of 50:1 was used as an eluent to carry out purification and separation by silica gel column chromatography to obtain the corresponding poly Substituted isoxazolidine derivatives, whose reaction formula is:

[0031]

[0032] The product had a purity of 99% and a yield of 85%. NMR data analysis is: 1 H NMR (400MHz, CDCl 3 ):δ H 7.31-7.25 (m, 2H), 7.18-7.16 (m, 5H), 7.11-7.06 (m, 5H), 6.97 (t, J = 7.3Hz, 1H), 6.83-6.82 (m, 2H), 4.94 ( d, J=8.8Hz, 1H), 4.67(dq, J=9.4, 6.0Hz, 1H), 3.63(t...

Embodiment 2

[0035] Into a 7mL round bottom flask, add 59mg (0.3mmol) diphenylnitrone, 47mg (0.45mmol) styrene, 1.2mg (0.0075mmol) photocatalyst and 4mL dichloromethane, stir well and pass nitrogen gas for 30 minutes and place Under the light of blue LEDs, light reaction was carried out at room temperature for 17 h. After the reaction was completed, the reaction solvent was concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether: ethyl acetate with a volume ratio of 30:1 was used as an eluent for purification and separation by silica gel column chromatography to obtain the corresponding poly Substituted isoxazolidine derivatives, whose reaction formula is:

[0036]

[0037] The product had a purity of 99% and a yield of 52%. The NMR data analysis is as follows: 1 H NMR (400MHz, CDCl 3 ):δ H 7.29-7.24(m,3H),7.16-7.10(m,5H),6.95-6.92(m,2H),4.99(d,J=7.9Hz,1H),4.50(t,J=7.6Hz,1H) ,4.33-4.29(m,1H),4.07(dd,J=14.2, 7.1Hz,1H).

[0038] 13 C NMR (10...

Embodiment 3

[0040] Into a 7mL round bottom flask, add 59mg (0.3mmol) diphenylnitrone, 53mg (0.45mmol) indene, 1.2mg (0.0075mmol) photocatalyst and 6mL dichloromethane, stir well, pass nitrogen gas for 30 minutes and place Under the light of blue LEDs, light reaction was carried out at room temperature for 12 hours. After the reaction was completed, the reaction solvent was concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether: ethyl acetate with a volume ratio of 40:1 was used as an eluent for purification and separation by silica gel column chromatography to obtain the corresponding poly Substituted isoxazolidine derivatives, whose reaction formula is:

[0041]

[0042] The product had a purity of 99% and a yield of 81%. The NMR data analysis is as follows: 1 H NMR (400MHz, CDCl 3 ):δ H 7.23-7.16(m,9H),7.06(t,J=8.2Hz,3H),6.93(t,J=7.3Hz,1H), 6.76(t,J=7.5Hz,1H),6.03(d,J =7.7Hz,1H),5.22(td,J=6.4,2.1Hz,1H), 5.01(d,J=8.7Hz,1H),4.44-4.40(m,1H)...

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Abstract

The invention relates to a polysubstituted isoxazolidine derivative and a preparation method thereof. The structural formula of the polysubstituted isoxazolidine derivative is as shown in a Formula (I) in the specification, wherein R1 and R2 are substituted aryl or alkyl; a substituent group on Ar can be alkoxy, halogen or alkyl; the substituted aryl is phenyl or naphthyl; and the alkyl generally comprises methyl, ethyl and cyclohexyl. The preparation method comprises the following steps: at room temperature, in an air or nitrogen atmosphere, dissolving a nitrone derivative as shown in a Formula (II), an olefin structure-containing compound as shown in a Formula (III) and a photocatalyst as shown in a Formula (IV) in an organic solvent, performing uniform mixing, performing illumination under blue LED lamps or filament lamps for hours; and after the reaction is completed, performing rotary evaporation on the solvent, and performing separation and purification through silica gel column chromatography to obtain the polysubstituted isoxazolidine derivative. The method solves the problems of need of a high temperature heating system, high energy consumption, strict conditions and high equipment requirements in the existing isoxazolidine derivative synthesis process; and the method is mild in conditions, simple, convenient to operate and high in yield.

Description

technical field [0001] The invention relates to a multi-substituted isoxazolidine derivative and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] The isoxazolidine skeleton widely exists in biologically active natural products and drug molecules. Due to its unique nitrogen-oxygen heterocyclic structure, it is also an important raw material intermediate for many chemical products and other natural products. For example, Through the reduction process, the chemical bond between nitrogen and oxygen can be cut to obtain γ-amino alcohol. According to literature reports, through a series of conversion reactions, various important chemical raw material intermediates, such as indole compound 1, benzotetrahydrofuran compound 2, and benzopyran compound 3, can be obtained. [0003] [0004] At present, there are not many reports on the synthesis of multi-substituted isoxazolidine derivatives, and most of the existing ...

Claims

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Application Information

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IPC IPC(8): C07D261/02C07D261/20
CPCC07D261/02C07D261/20
Inventor 夏吾炯郑乐伟郭小忠冯永胜杨双土章丽袁鹏吕传高徐赛仙
Owner QUZHOU YINGTE HIGH MOLECULAR MATERIAL CO LTD
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