Preparation method for oxazolone heterocyclic compounds

A technology for heterocyclic compounds and oxazolones, applied in the field of oxazolone heterocyclic compounds and preparation, can solve the problems of long reaction time, low reaction selectivity and high reaction cost

Inactive Publication Date: 2016-10-26
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] There are also many problems in the polymerization or ring-forming reaction of oxazolone compounds reported in existing literature, including harsh requirements on reaction temperature (cooling to minus 78°C) (eactivity of chiral exocyclic N-acyliminium ionswith aromatic derivatives); too long reaction time (reaction at 180°C for one day) (2-Dienylphenacyloxazolones and an intramolecular Diels–Alder approach to the A–B–C ringsystem of phenanthridone alkaloids); the reaction selectivity is low (the ratio of the two configuration products is 3.1:1)( Oxazolone cycloloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (2-epi-pumiliotoxin C); environmental unfriendly (One-Pot Stereoselective Synthesis of 1,2-Amino Alcohol Derivatives) and high reaction cost, etc.

Method used

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  • Preparation method for oxazolone heterocyclic compounds
  • Preparation method for oxazolone heterocyclic compounds
  • Preparation method for oxazolone heterocyclic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Example 1: 3-allyl-5-(3-allyl-2-oxooxazolidin-4-yl)oxazol-2(3H)-one

[0078]

[0079] Boron trifluoride ether solution (41 μL, 0.5 equiv.) was added dropwise to reaction substrate I-1 (77.6 mg, 0.62 mmol) in dichloromethane solution (2 ml), and the tube was sealed. The reaction mixture was stirred at 50°C for 12 hours. After the completion of the reaction was monitored with a TLC plate, the reaction was quenched with saturated sodium bicarbonate (5 ml) and stirred for 5 minutes. Dichloromethane was extracted 3 times (5mL×3), the organic phase was mixed and washed with water (10mL) and saturated brine (10mL) respectively, and finally dried over anhydrous sodium sulfate, filtered and then rotovaped to obtain a crude product. The crude product was subjected to silica gel column chromatography to obtain pure product IIa-1 (yield 98%).

[0080] Colorless oily liquid; Rf=0.21 (petroleum ether / ethyl acetate=3 / 2); IR(KBr)ν max 3198,3163,1746,1398,756cm -1 ; 1 H NMR (400...

Embodiment 2

[0081] Example 2: 5-(2-oxo-3-propyloxazolidin-4-yl)-3-propyloxazol-2(3H)-one

[0082]

[0083] Boron trifluoride diethyl ether solution (41 μL, 0.5 equiv.) was added dropwise to reaction substrate I-2 (79 mg, 0.62 mmol) in dichloromethane solution (2 ml), and the tube was sealed. The reaction mixture was stirred at 50°C for 12 hours. After the completion of the reaction was monitored with a TLC plate, the reaction was quenched with saturated sodium bicarbonate (5 ml) and stirred for 5 minutes. Dichloromethane was extracted 3 times (5mL×3), the organic phase was mixed and washed with water (10mL) and saturated brine (10mL) respectively, and finally dried over anhydrous sodium sulfate, filtered and then rotovaped to obtain a crude product. The crude product was subjected to silica gel column chromatography to obtain pure product IIa-2 (yield 85%).

[0084] Colorless oily liquid; Rf=0.22 (petroleum ether / ethyl acetate=3 / 2); IR(KBr)ν max 3135, 2966, 1751, 1400, 1131, 754cm ...

Embodiment 3

[0085] Example 3: 3-Benzyl-5-(3-benzyl-2-oxooxazolidin-4-yl)oxazol-2(3H)-one

[0086]

[0087] Boron trifluoride diethyl ether solution (41 μL, 0.5 equiv.) was added dropwise to reaction substrate I-3 (109 mg, 0.62 mmol) in dichloromethane solution (2 ml), and the tube was sealed. The reaction mixture was stirred at 50°C for 12 hours. After the completion of the reaction was monitored with a TLC plate, the reaction was quenched with saturated sodium bicarbonate (5 ml) and stirred for 5 minutes. Dichloromethane was extracted 3 times (5mL×3), the organic phase was mixed and washed with water (10mL) and saturated brine (10mL) respectively, and finally dried over anhydrous sodium sulfate, filtered and then rotovaped to obtain a crude product. The crude product was subjected to silica gel column chromatography to obtain pure product IIa-3 (yield 87%).

[0088] White solid (melting point: 125-126°C); Rf=0.33 (petroleum ether / ethyl acetate=3 / 2); IR(KBr)ν max 3239,3093,1748,1400,...

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Abstract

The invention relates to a preparation method for N-substituted oxazolone polymerized compounds. According to the method, the easily available reagent, boron trifluoride ether, is used as a catalyst, and dimerization, cascaded dimerization / cyclization, terminal butylene cyclization and secondary cyclization among N-substituted oxazolone molecules are influenced under mild reaction conditions. The method is not sensitive to water in a reaction system, and identical reactions and same yield and rate may be realized under aqueous conditions. The novel preparation method with the advantages of mild reaction condition and high-efficiency conversion can be more extensively applied to synthesis of a plurality of molecules and industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicinal chemistry, and relates to oxazolone heterocyclic compounds and a preparation method. Background technique [0002] In the fields of organic synthesis and medicinal chemistry, efficient and environmentally friendly synthesis of complex and diverse molecular structures has always been the goal of laboratories and industries. This goal is difficult and challenging in practice. [0003] According to reports by Argade et al. (E-Journal of Chemistry, Vol.5, No.1, pp.120-129, January 2008), oxazolone has become one of the most attractive molecules among heterocyclic compounds due to its wide range of biological activities. First, it is also an important intermediate in the field of total synthesis of natural products. Oxazolone compounds have a wide range of uses, and can be used in medicine, pesticides, polymer improvement, organic synthesis intermediates, etc. The heterocyclic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/38C07D498/14C07D498/04C07D498/18C07D498/22A61P35/00
CPCC07D263/38C07D498/04C07D498/14C07D498/18C07D498/22Y02P20/55
Inventor 曹蓓邹成周兴华徐化成徐标P·K·阿加瓦尔C·K·I·那迦贺耘
Owner CHONGQING UNIV
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