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Preparation method of 2-pyrrolidinone compound

A pyrrolidone and compound technology, applied in the field of preparation of 2-pyrrolidone compounds, to achieve the effect of avoiding metal residues and high efficiency

Active Publication Date: 2018-08-17
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Despite the above achievements, it remains desirable and challenging to explore facile synthetic strategies to prepare 2-pyrrolidinones under mild conditions.

Method used

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  • Preparation method of 2-pyrrolidinone compound
  • Preparation method of 2-pyrrolidinone compound
  • Preparation method of 2-pyrrolidinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0030] Embodiment 1-10 is reaction condition optimization test

[0031]

Embodiment 1

[0033] Add 1,6-enyne compound (40mg, 0.2mmol) shown in formula II-1 in the schlenk bottle, azidotrimethylsilane (TMSN 3 , 46mg, 0.4mmol), N-chlorosuccinimide (NCS, 53.2g, 0.4mmol), iodobenzene acetate (PIDA, 130mg, 0.4mmol), then add solvent dichloroethane (DCE, 2mL) , then the reactor was stirred and reacted in an air atmosphere and at room temperature, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 1 hour). After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove the solvent, and the residue was passed through a column layer Analysis and separation (elution solvent: ethyl acetate / n-hexane) gave the target product I-1. (0.0386g, 70% yield, 9:1 Z / E mixture, yellow oily liquid); 1 H NMR (400MHz, CDCl 3 )δ: 7.72(d, J=8.4Hz, 2H), 7.42(t, J=7.6Hz, 2H), 7.21(t, J=7.6Hz, 1H), 6.44(s, 0.1H), 6.23(s , 0.9H), 4.52(d, J=2.0Hz, 2H), 3.73(d, J=11.6Hz, 1H), 3.45(d, J=12.0Hz, IH), 1.38(s...

Embodiment 2

[0035]

[0036] Add 1,6-enyne compound (40mg, 0.2mmol) shown in formula II-1 in the schlenk bottle, azidotrimethylsilane (TMSN 3, 46mg, 0.4mmol), N-chlorosuccinimide (NCS, 53.2g, 0.4mmol), iodobenzene trifluoroacetate (172mg, 0.4mmol), then add solvent dichloroethane (DCE, 2mL) , then the reactor was stirred and reacted in an air atmosphere and at room temperature, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 1 hour). After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove the solvent, and the residue was passed through a column layer Analysis and separation (elution solvent: ethyl acetate / n-hexane) gave the target product I-1 (yield 45%).

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Abstract

The invention relates to a preparation method of a 2-pyrrolidinone compound. According to the method, a 1, 6-enyne compound serves as a raw material, iodosobenzene diacetate serves as an oxidizing agent and reacts with trimethyl silicon-based azide and N-chlorosuccinimide in organic solvents, and the 2-pyrrolidinone compound is conveniently prepared by excellent yield.

Description

technical field [0001] The application belongs to the field of organic synthesis methodology, in particular to a preparation method of 2-pyrrolidone compounds. Background technique [0002] 2-Pyrrolidone compounds are a class of pyrrolidine compounds with a five-membered lactam ring, which widely exist in natural products and various synthetic compounds, and are also widely used because of their various biological activities. In the field of medicine, the following formula 1 lists a variety of biologically active compounds containing 2-pyrrolidone compounds that have been disclosed and used in the prior art. [0003] [0004] Due to the rich biological activity of 2-pyrrolidone compounds, the development of efficient synthetic methods for this building block is one of the focuses of synthetic chemists, and the most common methods for obtaining 2-pyrrolidone core structures usually rely on the prior formation of Ring expansion or contraction of a ring, cyclization between...

Claims

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Application Information

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IPC IPC(8): C07D207/38
CPCC07D207/38
Inventor 包雯慧魏文廷高乐涵王昕晔
Owner NINGBO UNIV
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