Preparation method of 2-pyrrolidone derivative

A technology of pyrrolidone and derivatives, which is applied in the field of preparation of 2-pyrrolidone derivatives and achieves the effect of adapting to a wide range

Active Publication Date: 2020-02-07
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods require the use of acid additives or transition metal catalysts, so the realization of cyclization reactions without any transition metal catalysts and additive systems is considered to be one of the most promising synthetic strategies due to its economical and environmentally friendly characteristics.

Method used

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  • Preparation method of 2-pyrrolidone derivative
  • Preparation method of 2-pyrrolidone derivative
  • Preparation method of 2-pyrrolidone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] In the Schlenk bottle, add 1,6-enyne compound (39.8 mg, 0.2 mmol) shown in formula 1a, p-methoxybenzaldehyde (27.2 mg, 0.2 mmol) shown in formula 2a, tert-butanol peroxide ( TBHP, 36.0 mg, 0.4 mmol) and ethyl acetate (2.0 mL), then the reactor was stirred and reacted in an air atmosphere at 90 ° C, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 12 hours), and the reaction was completed Afterwards, the reaction solution was concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1 (14% yield); 1 H NMR (500MHz, CDCl 3 )δ: 7.90-7.88(m, 2H), 7.76-7.74(m, 2H), 7.39(t, J=7.5Hz, 2H), 7.15(t, J=7.5Hz, 1H), 6.90-6.88(m , 2H), 5.09(t, J=2.0Hz, 1H), 4.98(d, J=2.5Hz, 1H), 4.74-4.70(m, 1H), 4.96-4.52(m, 1H), 3.84(s, 3H), 3.66(d, J=18.0Hz, 1H), 3.45(d, J=18.0Hz, 1H), 1.418(s, 3H); 13 CNMR...

Embodiment 2

[0036] No oxidizing agent was added, other conditions were the same as in Example 1, and the yield of the target product I-1 was 0%.

Embodiment 3

[0038] The reaction temperature was raised to 100° C., and the rest of the conditions were the same as in Example 1. The yield of the target product I-1 was 32%.

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Abstract

The invention relates to a preparation method of a 2-pyrrolidone derivative. According to the method, 1,6-eneyne compounds, carbonyl compounds, oxidizing agents and organic solvent are added into a Schlenk reaction flask, the mixture is stirred on the conditions of certain temperature and the air atmosphere to carry out free radical cyclization reaction.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a preparation method of 2-pyrrolidone derivatives. Background technique [0002] Radical cyclizations of enynes have gradually emerged as a straightforward and highly step-economical strategy for the construction of complex cyclic compounds. In recent years, transition metal-catalyzed reaction systems have been rapidly developed and widely used in this type of reaction. However, the use of transition metal catalysts not only increases the reaction cost, but also leaves metal residues in the product, which limits its further application in biochemistry. Therefore, it is of great scientific and practical significance to develop the radical cyclization reactions of enynes in metal-free systems. [0003] Carbonyl compound C(sp 2 The oxidative functionalization of )-H bonds has become an important method for the rapid introduction of carbonyl groups in modern syntheti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/38C07D409/06
CPCC07D207/38C07D409/06
Inventor 魏文廷曹婷婷徐旭东宋思哲
Owner NINGBO UNIV
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