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Pyrrolidone compound synthesis method

A synthetic method and technology of pyrrolidone, applied in the direction of organic chemistry, can solve the problems of limited reliable methods, cumbersome operation, harsh reaction conditions, etc., and achieve the effects of wide application range, simple synthesis process, and easy-to-obtain raw materials

Active Publication Date: 2019-02-22
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although pyrrolidone compounds have shown important application value in many aspects, reliable methods for the synthesis of such compounds are still very limited, and these methods often have problems such as harsh reaction conditions and cumbersome operations.

Method used

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  • Pyrrolidone compound synthesis method
  • Pyrrolidone compound synthesis method
  • Pyrrolidone compound synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015]

[0016] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (1mmol, 181mg), potassium iodide (1mmol, 166mg) and potassium hydrogen persulfate composite salt (Oxone, 615mg, 1mmol) to a 10mL Shrek tube. ), evacuated and filled with oxygen (1atm), then placed in an oil bath at 80°C and stirred for 12h. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=3 / 1) to obtain a white solid product 2a (47 mg, 58%). The characterization data of this compound are as follows: 1 H NMR(600MHz, CDCl 3 )δ2.09(quint,J=7.8Hz,2H), 2.54(t,J=7.8Hz,2H), 3.80(t,J=7.2Hz,2H), 7.07(t,J=7.2Hz,1H) ,7.30(t,J=7.8Hz,2H),7.54(d,J=8.4Hz,2H). 13 C NMR(150MHz, CDCl 3 )δ18.1,32.8,48.8,120.0,124.5,128.8,139.4,174.2.HRMS calcd forC 10 H 11 NNaO:184.0733[M+Na] + ,found:18...

Embodiment 2

[0018] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (0.25mmol, 45mg), potassium iodide (0.5mmol, 83mg) and Oxone (308mg, 0.5mmol) to a 10mL Shrek tube in sequence, and vacuum After being filled with oxygen (1atm), it was placed in an oil bath at 80°C and stirred for 12 hours. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate = 3 / 1) to obtain a white solid product 2a (19 mg, 23%).

Embodiment 3

[0020] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), anhydrous copper acetate (0.5mmol, 91mg), potassium iodide (0.5mmol, 83mg) and Oxone (308mg, 0.5mmol) to a 10mL Shrek tube in sequence, and vacuumize After being filled with oxygen (1atm), it was placed in an oil bath at 80°C and stirred for 12 hours. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=3 / 1) to obtain a white solid product 2a (25 mg, 31%).

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Abstract

The invention discloses a pyrrolidone compound synthesis method, and belongs to the technical field of organic synthesis. Saturated cyclic tertiary amine 1 is added into solvents, and heating reactionis performed in the presence of oxidizing agent, cupric salt, potassium hydrogen persulfate compound salt (Oxone) and oxygen mixture, additives, elementary iodine or iodated metal salt and the like to obtain pyrrolidone 2. According to the method, a pyrrolidone compound is synthesized by cascade reaction of oxidization retraction, decarbonylation and in-situ oxidization of saturated cyclic tertiary amine compounds, the method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and an economical, practical, green and environment-friendly novel method is provided for synthesis of the pyrrolidone compound.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing pyrrolidone compounds. Background technique [0002] As an important type of nitrogen-containing heterocyclic skeleton, pyrrolidone is widely present in natural products. It is worth emphasizing that many natural products and synthetic compounds containing pyrrolidone structural units have strong biological activity and excellent luminescence properties, and have played an important role in the development of new drugs and optoelectronic materials. In addition, pyrrolidone compounds also have rich reaction properties and are commonly used reagents in organic synthetic chemistry. At present, although pyrrolidone compounds have shown important application value in many aspects, the reliable methods that can be used for the synthesis of such compounds are still very limited, and these methods often have problems such as harsh reaction condi...

Claims

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Application Information

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IPC IPC(8): C07D207/267C07D207/27C07D409/04
CPCC07D207/267C07D207/27C07D409/04
Inventor 范学森王芳张新迎何艳
Owner HENAN NORMAL UNIV
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