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Free radical cyclization reaction method of 1, 6-enyne compound and azoalkyl nitrile

An azo alkyl nitrile, cyclization reaction technology, applied in the direction of organic chemistry, etc., to achieve a wide range of effects

Active Publication Date: 2019-11-29
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, azoalkylnitriles are seldom reported as a two-carbon unit to participate in radical cycloaddition reactions by means of intramolecular cyclization reactions after cyanation reactions.

Method used

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  • Free radical cyclization reaction method of 1, 6-enyne compound and azoalkyl nitrile
  • Free radical cyclization reaction method of 1, 6-enyne compound and azoalkyl nitrile
  • Free radical cyclization reaction method of 1, 6-enyne compound and azoalkyl nitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] In the Schlenk bottle, add 1,6-enyne compound (39.8mg, 0.2mmol) shown in formula 1a, azoalkylnitrile (65.6mg, 0.4mmol) shown in formula 2a, cuprous iodide (CuI, 7.6mg, 0.04mmol), triethylamine (Et 3 N, 4.0mg, 0.04mmol), H 2 O / MeCN (v:v=4:1, 2.0mL), then the reactor was stirred and reacted in an air atmosphere at 60°C, and the reaction process was monitored by TLC until the raw materials disappeared (reaction time was 16 hours). After the reaction was completed, , the reaction solution was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and 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 (71% yield); 1 H NMR (500MHz, CDCl 3)δ: 7.66(d, J=7.5Hz, 2H), 7.40(t, J=8.0Hz, 2H), 7.19(t, J=7.5Hz, 1H), 6.01(s, 1H), 4.75(d, J=14.0Hz, 1H), 4.37(d, J=14.0Hz, 1H), 2.18-2.08(m, 2H), ...

Embodiment 2

[0035] As the base, 1,8-diazabicycloundec-7-ene was used instead of triethylamine, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 61%.

Embodiment 3

[0037] As the base, potassium acetate was used instead of triethylamine, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 52%.

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Abstract

The invention relates to a regioselective free radical cyclization reaction method of a 1, 6-enyne compound and azoalkyl nitrile under a mild condition. According to the method, the 1, 6-enyne compound, an azoalkyl nitrile compound, a catalyst, alkali and a solvent are added into a Schlenk reaction bottle for stirring reaction under certain temperature and air atmosphere conditions, thus obtaininga cyclization product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and in particular relates to a regioselective free radical cyclization reaction method of 1,6-enynes and azoalkylnitriles under mild conditions. Background technique [0002] In polymer chemistry, azoalkylnitriles are widely used as free radical initiators. Traditionally, it only initiates free radical processes and does not participate in chemical reactions. In recent years, azoalkylnitriles can be used as a safe and low-toxic cyanation reagent in the presence of copper catalysts and / or oxidants. Against this background, chemists have developed the cyanation reactions of azoalkylnitriles with alkenes, alkynes, and enyne derivatives. However, azoalkylnitriles are seldom reported as a two-carbon unit to participate in free radical cycloaddition reactions by means of intramolecular cyclization after cyanation. [0003] The inventor has carried out in-depth research on the free radical cyclizat...

Claims

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Application Information

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IPC IPC(8): C07D209/46
CPCC07D209/46
Inventor 曹婷婷魏文廷黄训杰宋思哲
Owner NINGBO UNIV
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