3H-2-pyrrolidone compounds and synthesis method thereof

A pyrrolidone and synthetic method technology, applied in the direction of organic chemistry, etc., can solve the problems of 3H-2-pyrrolidone limited synthetic method, low preparation cost, and difficult synthesis, and achieve high relative yield and purity, low preparation cost and easy operation simple effect

Active Publication Date: 2018-01-26
BAOJI UNIV OF ARTS & SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis methods of 3H-2-pyrrolidone are very limited, especially the 3H-2-pyrrolidone compounds containing special functional groups or substituents, because of the difficulty of synthesis, there is no low-cost preparation method reported

Method used

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  • 3H-2-pyrrolidone compounds and synthesis method thereof
  • 3H-2-pyrrolidone compounds and synthesis method thereof
  • 3H-2-pyrrolidone compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: The synthesis of 3H-2-pyrrolidone (2a), its structural formula is specifically as follows:

[0021]

[0022] Add 1mmol of enaminoester (1a) and 1mmol of 2,2,6,6-tetramethylpiperidine-nitroxyl radical into 5mL of ethylene glycol dimethyl ether, then add 1mmol of potassium persulfate, and reflux for 12h. After the reaction was finished, the reaction solution was washed with 10 mL of saturated sodium carbonate solution, then extracted with ethyl acetate (10 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, and the crude product was subjected to fast silica gel column chromatography (V 乙酸乙酯 :V 石油醚 =10:1), the product 155mg was obtained, and the calculated yield was 88%.

[0023] Its main physical and chemical properties are as follows:

[0024] White solid, melting point 144-145°C; 1 H NMR (400MHz, CDCl 3 ):δ8.01(br,1H),7.65-7.68(m,2H),7.56-7.59(m,2H),7.47-7.53(m,3H),7.34-7.39(m,3H),3.74(s ,3H),3.58(s,3H); ...

Embodiment 2

[0025] Embodiment 2: The synthesis of 3H-2-pyrrolidone (2b), its structural formula is specifically as follows:

[0026]

[0027] Add 1mmol of enaminoester (1b) and 1mmol of 2,2,6,6-tetramethylpiperidine-nitroxyl radical into 5mL of ethylene glycol dimethyl ether, then add 1mmol of potassium persulfate, and reflux for 12h. After the reaction was finished, the reaction solution was washed with 10 mL of saturated sodium carbonate solution, then extracted with ethyl acetate (10 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, and the crude product was subjected to fast silica gel column chromatography (V 乙酸乙酯 :V 石油醚 =10:1), the product 170mg was obtained, and the calculated yield was 90%.

[0028] Its main physical and chemical properties are as follows:

[0029] yellow oil; 1 H NMR (400MHz, CDCl 3 ):δ8.61(br,1H),7.64-7.67(m,2H),7.57-7.59(m,2H),7.43-7.50(m,3H),7.33-7.37(m,3H),4.19-4.31 (m,2H),4.03-4.09(m,2H),1.24(t,J=7.1Hz,3H...

Embodiment 3

[0030] Embodiment 3: Synthesis of 3H-2-pyrrolidone (2c), its structural formula is as follows:

[0031]

[0032] Add 1mmol of enaminoester (1c) and 1mmol of 2,2,6,6-tetramethylpiperidine-nitroxyl radical into 5mL of ethylene glycol dimethyl ether, then add 1mmol of potassium persulfate, and reflux for 12h. After the reaction was finished, the reaction solution was washed with 10 mL of saturated sodium carbonate solution, then extracted with ethyl acetate (10 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure, and the crude product was subjected to fast silica gel column chromatography (V 乙酸乙酯 :V 石油醚 =10:1), the product 145mg was obtained, and the calculated yield was 72%.

[0033] Its main physical and chemical properties are as follows:

[0034] White solid, melting point: 166-168°C; 1 H NMR (400MHz, CDCl 3 ):δ8.02(br,1H),7.57(d,J=8.2Hz,2H),7.46(d,J=8.3Hz,2H),7.29(d,J=8.0Hz,2H),7.17(d ,J=8.1Hz,2H),3.77(s,3H),3.58(s,3H),2.43(s,...

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Abstract

The invention provides 3H-2-pyrrolidone compounds and a synthesis method thereof. According to the method, persulfate is taken as an oxidizing agent to promote a cyclizing rearrangement reaction of enamine compounds, 3H-2-pyrrolidone compounds are simple to prepare, the preparation cost is lower, the relative yield and purity are higher, and environmental pollution is low. Besides, the provided 3H-2-pyrrolidone compounds are a series of compounds with novel structures and potential application value, can be converted into important chemical products such as substituted pyrrole, butyrolactam, pyrrolidine, gamma-ketonic acid, butyric acid derivatives and the like and are important organic synthesis intermediates.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and specifically relates to a 3H-2-pyrrolidone compound and its synthesis and purification methods. Background technique [0002] Polyhydropyrrolidone is a special aza five-membered ring compound, which has important applications in the synthesis of a variety of molecules with physiological functions, pharmaceutical activities or optical properties (Journal of Medicinal Chemistry, 2005, 48, 5412; Journal of Natural Products, 2014, 77, 983). As a special class of pyrrolidone compounds, 3H-2-pyrrolidone can also be converted into important chemicals such as substituted pyrrole, butyrolactam, pyrrolidine, γ-keto acid and butyric acid derivatives, and is an important organic synthesis intermediate (Advanced Synthesis & Catalysis, 358, 3010; Organic Letters, 2017, 19, 1172). However, the synthesis methods of 3H-2-pyrrolidone are very limited, especially for 3H-2-pyrrolidone compounds cont...

Claims

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Application Information

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IPC IPC(8): C07D207/38C07D409/14C07D405/14
Inventor 高鹏白梓静凡明锦王娟杨得锁
Owner BAOJI UNIV OF ARTS & SCI
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