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Method for preparing 2-pyrrolidone compound by 1,6-enyne nitration cyclization reaction

A pyrrolidone and compound technology, applied in the field of synthesis of 2-pyrrolidone compounds, to achieve a wide range of effects

Active Publication Date: 2018-11-02
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some synthetic methods of such scaffolds have been reported, it is still challenging to develop green, economical, and highly selective synthetic strategies to prepare 2-pyrrolidinones under mild conditions.

Method used

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  • Method for preparing 2-pyrrolidone compound by 1,6-enyne nitration cyclization reaction
  • Method for preparing 2-pyrrolidone compound by 1,6-enyne nitration cyclization reaction
  • Method for preparing 2-pyrrolidone compound by 1,6-enyne nitration cyclization reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Add the 1,6-enyne compound (40mg, 0.2mmol) represented by formula 1a, t-butyl nitrite (t-BuONO, 61.8mg, 0.6mmol) into the Schlenk bottle, and then add the solvent tetrahydrofuran (THF, 2mL) , then the reactor was stirred and reacted under air atmosphere and 90°C, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 12 hours). 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 Chromatographic separation (elution solvent: ethyl acetate / n-hexane) gave the target product I-1. (60% yield); 1 H NMR (400MHz, DMSO-d6) δ: 7.76(d, J=7.6Hz, 2H), 7.43(t, J=8.0Hz, 2H), 7.20(t, J=7.2Hz, 1H), 5.41(t , J=2.4Hz, 1H), 5.28(t, J=2.0Hz, 1H), 5.06(t, J=15.2Hz, 2H), 4.68-4.63(m, 1H), 4.47-4.43(m, 1H) , 1.30(s, 3H); 13 C NMR (100MHz, DMSO-d6) δ: 174.1, 143.0, 139.4, 129.3, 125.0, 120.3, 109.1, 79.3, 51.5, 49.1, 23.2; HRMS...

Embodiment 2

[0030] The solvent 1,4-dioxane was used instead of tetrahydrofuran, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 83%.

Embodiment 3

[0032] The solvent acetonitrile was used instead of tetrahydrofuran, and the rest of the conditions were the same as in Example 1, and the yield of the target product I-1 was 28%.

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Abstract

The invention relates to a green synthesis method of a 2-pyrrolidone compound without any external additives. The method comprises the following steps: adding 1,6-eneyne (1), tert-butyl nitrite of formula 2a and solvent 1,4-dioxane to a Schlenk reaction bottle, and placing the reaction bottle under a certain temperature and air atmosphere for stirring and reaction, and monitoring the progress of the reaction by TLC or GC until the complete reaction of the raw materials. The desired product 2-pyrrolidone compound (I) is obtained by post-treatment; the formula is shown in the specification.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a method for synthesizing 2-pyrrolidone compounds. Background technique [0002] 2-Pyrrolidone compounds are a class of nitrogen heterocyclic 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. field of medicine. As a subclass of 2-pyrrolidones, nitro-substituted 2-pyrrolidone skeletons are also very important structural units and have broad application prospects. [0003] The inventors have found that the common methods for the synthesis and preparation of 2-pyrrolidone core structures in the prior art include ring expansion reactions of previously formed three-membered rings or four-membered rings, ring contraction reactions of six-membered rings, two groups The cyclization reaction between the points, etc. Although some synth...

Claims

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Application Information

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IPC IPC(8): C07D207/38C07D207/48C07D211/82
CPCC07D207/38C07D207/48C07D211/82
Inventor 徐旭东魏文廷宋思哲潘文文
Owner NINGBO UNIV
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