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A kind of polysubstituted oxazoline compound and preparation method thereof

An oxazoline compound and multi-substitution technology, applied in the direction of organic chemistry, can solve the problems of cumbersome raw material synthesis steps, poor functional group tolerance, harsh reaction conditions, etc. The effect of mild conditions

Active Publication Date: 2022-07-05
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Another object of the present invention is to provide a method for preparing the above-mentioned multi-substituted oxazoline compound, which aims to solve the problems of cumbersome raw material synthesis steps, expensive catalysts, harsh reaction conditions, poor tolerance of functional groups, and harsh reaction conditions in the existing methods.

Method used

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  • A kind of polysubstituted oxazoline compound and preparation method thereof
  • A kind of polysubstituted oxazoline compound and preparation method thereof
  • A kind of polysubstituted oxazoline compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] N-(1-phenylvinyl)acetamide (0.225 mmol, 36.3 mg), benzoylthioylide (0.15 mmol, 29.4 mg), and silver bis-trifluoromethanesulfonimide were added to the 4 mL reaction flask. Salt (0.015 mmol, 5.8 mg), pivalic acid (0.15 mmol, 15.3 mg) and 1 mL of trifluorotoluene; nitrogen was blown into the reaction flask for 30 s, and heated and stirred, and heated to 100 ° C, and the stirring time was 24 h; After the reaction, the reaction solution was cooled to room temperature without post-treatment, and was separated by silica gel column chromatography to obtain a pure product as a yellow solid; the yield was 85% (1.9:1).

[0032] The H NMR data of this product are as follows: 1 HNMR (400MHz, Chloroform-d) δ 7.71 (dd, J=8.4, 1.4Hz, 2H), 7.62–7.57 (m, 1H), 7.45–7.31 (m, 7H), 5.71 (s, 1H), 2.26 (s,3H),1.40(s,3H).

[0033] Thus, the product obtained in the embodiment of the present invention is (trans-2,4-dimethyl-4-phenyl-4,5-dihydrooxazol-5-yl)(phenyl)methanone, and its chemical str...

Embodiment 2

[0036] N-(1-(4-chlorophenyl)vinyl)acetamide (0.225mmol, 44.0mg), benzoylthioylide (0.15mmol, 29.4mg), bistrifluoromethyl were added to the 4mL reaction flask, respectively. Sulfonyl imide silver salt (0.015mmol, 5.8mg), pivalic acid (0.15mmol, 15.3mg) and 1 mL of trifluorotoluene; blow nitrogen into the reaction flask for 30s, heat and stir, and heat to 100°C, The stirring time was 24h; after the reaction, the reaction solution was cooled to room temperature without post-treatment, and the pure product was separated by silica gel column chromatography to obtain a yellow oily product; the yield was 78% (2.1:1).

[0037] The H NMR data of this product are as follows: 1HNMR (400MHz, Chloroform-d) δ 7.71 (dd, J=8.3, 1.3Hz, 2H), 7.64–7.59 (m, 1H), 7.44 (td, J=7.3, 0.9Hz, 2H), 7.36–7.31 (m, 2H), 7.28–7.23(m, 2H), 5.63(s, 1H), 2.25(s, 3H), 1.37(s, 3H).

[0038] Thus, the product obtained in the embodiment of the present invention is (trans-4-(4-chlorophenyl)-2,4-dimethyl-4,5-dihydr...

Embodiment 3

[0041] N-(1-phenylvinyl)propionamide (0.225 mmol, 39.4 mg), benzoylthioylide (0.15 mmol, 29.4 mg), and silver bis-trifluoromethanesulfonimide were added to a 4 mL reaction flask. Salt (0.015 mmol, 5.8 mg), pivalic acid (0.15 mmol, 15.3 mg) and 1 mL of trifluorotoluene; nitrogen was blown into the reaction flask for 30 s, and heated and stirred, and heated to 100 ° C, and the stirring time was 24 h; After the reaction, the reaction solution was cooled to room temperature without post-treatment, and was separated by silica gel column chromatography to obtain a pure product in the form of yellow oil; the yield was 93% (1.7:1).

[0042] The H NMR data of this product are as follows: 1 HNMR (400MHz, Chloroform-d) δ 7.73–7.69 (m, 2H), 7.62–7.56 (m, 1H), 7.40 (dd, J=14.9, 7.6Hz, 3H), 7.36–7.29 (m, 4H) ,5.69(s,1H),2.57(qd,J=7.7,3.2Hz,2H),1.40(s,3H),1.37(d,J=15.0Hz,3H).

[0043] Thus, the product obtained in the embodiment of the present invention is (trans-2-ethyl-4-methyl-4-phenyl-...

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Abstract

The invention discloses a polysubstituted oxazoline compound and a preparation method thereof. In the present invention, 0.15-0.45 mmol N-(1-substituted vinyl) substituted amide, 0.15 mmol α-carbonylthio ylide, 10 mol% silver salt catalyst and 0.15 mmol additive are sequentially added into Schlenk sealed tube under nitrogen atmosphere to mix, The mixture was heated to 60-120° C. and stirred for 12-24 h, then the reaction solution was cooled to room temperature, and the polysubstituted oxazoline compound was obtained by separation by silica gel column chromatography. The reaction conditions required by the preparation method of the invention are mild, the raw materials used include enamide and sulfur ylide are cheap and easy to obtain, and the substrate is suitable for a wide range. Compared with the traditional oxazoline synthesis route, the method is greener, non-toxic, and has more synthetic steps. The target product can be obtained simply and in high yield, and the obtained oxazoline compound has potential application prospects in the field of pharmaceutical synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a polysubstituted oxazoline compound and a preparation method thereof. Background technique [0002] Due to its special structure and five-membered ring containing nitrogen and oxygen, oxazoline exhibits unique biological activity and properties, and is used in many fields such as pesticides, materials science, and medicine. Therefore, the synthesis of oxazoline compounds has received extensive attention from organic chemists. As a nitrogen-oxygen heterocyclic ring, oxazoline is easy to form hydrogen bonds with protons and easy to coordinate with metals, and can be used as guiding groups and ligands. It is worth noting that oxazoline compounds can bind to many enzymes and receptors in the organism, showing effective biological activities, such as antifungal, anti-tuberculosis, anti-convulsant, hypoglycemic, analgesic and anti-inflammatory, etc. It ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/14
CPCC07D263/14
Inventor 胡绪红刘瑞华高雅
Owner NANJING TECH UNIV
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