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Free radical cyclization reaction method of 1,6-eneyne compound and ether compound

A technology of ether compounds and cyclization reaction, applied in the direction of organic chemistry, etc., can solve the problems of limiting the diversity of organic molecules, and achieve the effect of adapting to a wide range

Active Publication Date: 2020-04-03
NINGBO UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, previously reported reactions are usually accompanied by intramolecular tandem cyclization reactions, which greatly limit the diversity of organic molecular construction.

Method used

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  • Free radical cyclization reaction method of 1,6-eneyne compound and ether compound
  • Free radical cyclization reaction method of 1,6-eneyne compound and ether compound
  • Free radical cyclization reaction method of 1,6-eneyne compound and ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Add 1,6-enyne compound represented by formula 1a (39.8 mg, 0.2 mmol), tetrahydrofuran (0.5 mL), tert-butyl peroxybenzoate (TBPB, 155.2 mg, 0.8 mmol), cesium carbonate to a Schlenk bottle (Cs 2 CO 3, 78.2mg, 0.24mmol), then the reactor was stirred and reacted in an air atmosphere at 85°C, and the reaction process was monitored by TLC until the raw material disappeared (reaction time was 20 hours). After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove Solvent, the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1 (78% yield, d.r.=5.7:1); 1 H NMR (400MHz, DMSO-d6) δ: 7.74 (d, J=8.4Hz, 0.3H), 7.69 (d, J=8.0Hz, 1.7H), 7.42-7.36 (m, 2H), 7.17-7.12( m, 1H), 5.29-5.02(m, 2H), 4.51(d, J=14.4Hz, 1H), 4.38(d, J=16.0Hz, 1H), 3.90-3.84(m, 1H), 3.60-3.54 (m, 1H), 3.45-3.40(m, 1H), 2.01-1.95(m, 1H), 1.89-1.82(m, 1H), 1.78-1.63(m, 3H), 1.44-1.37(m, ...

Embodiment 2

[0038] 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

[0040] No base was added, and the other conditions were the same as in Example 1, and the yield of the target product I-1 was 23%.

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Abstract

The invention relates to a regioselective free radical cyclization reaction method of a 1,6-eneyne compound and an ether compound in a transition-metal-free catalyst system. The method comprises the following steps: adding a 1,6-enyne compound, an ether compound, an alkali additive and an oxidizing agent into a Schlenk reaction bottle, and carrying out a stirring reaction at a certain temperatureunder an air atmosphere condition to obtain a cyclization product 2-pyrrolidone compound.

Description

technical field [0001] The application belongs to the field of organic synthesis, and specifically relates to a regioselective free radical cyclization reaction method of 1,6-enynes and (thio)ether compounds without a transition metal catalyst system. Background technique [0002] α-functionalized ether derivatives are widely found in medicines, natural products and agrochemicals, exhibiting a variety of biological activities. Formula 1 is a representative α-functionalized ether derivative with biological activity. Therefore, it is imminent to prepare this kind of skeleton through the α-C-H functionalization reaction of cheap and easy-to-obtain ether compounds. In recent years, chemists have developed functional group reactions of ether compounds with ketones, carboxylic acids, amines, aromatics, heteroaromatics, alkenes, alkynes, and enyne derivatives. Among them, the reaction between ether compounds and enyne derivatives has attracted much attention. On the one hand, it i...

Claims

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Application Information

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IPC IPC(8): C07D405/06C07D207/38
CPCC07D405/06C07D207/38
Inventor 魏文廷曹婷婷高乐涵宋思哲
Owner NINGBO UNIV
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