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Free radical cyclization reaction method of 1, 6-diene and azoalkyl nitrile in water phase

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: 2020-05-26
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no method has been reported for the highly regioselective introduction of two-carbon synthons via radical cyclization reactions of 1,n-dienes.

Method used

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  • Free radical cyclization reaction method of 1, 6-diene and azoalkyl nitrile in water phase
  • Free radical cyclization reaction method of 1, 6-diene and azoalkyl nitrile in water phase
  • Free radical cyclization reaction method of 1, 6-diene and azoalkyl nitrile in water phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] In the Schlenk bottle, add 1,6-diene compound (40.2mg, 0.2mmol) shown in formula 1a, azoalkylnitrile (65.6mg, 0.4mmol) shown in formula 2a, H 2 O / MeCN (v:v=1:3, 2.0mL), 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 materials disappeared (reaction time was 12 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 (82% yield, d.r.=4:1); 1 H NMR (500MHz, CDCl 3 )δ: 7.67-7.61(m, 2H), 7.38(t, J=8.0Hz, 2H), 7.17(t, J=7.5 Hz, 1H), 4.17-4.13(m, 0.2H), 4.09-4.05( m, 0.8H), 3.44-3.41(m, 0.2H), 3.39-3.37(m, 0.8H), 2.66-2.61(m, 1H), 2.55-2.50(m, 1H), 2.38(t, J= 15.0Hz, 1H), 1.78(t, J...

Embodiment 2

[0033] h 2 The volume ratio of O and MeCN becomes 1: 1, and all the other conditions are the same as in Example 1, and the yield of the target product I-1 is 83%.

Embodiment 3

[0035] h 2 The volume ratio of O and MeCN was changed to 3: 1, all the other conditions were the same as in Example 1, and the yield of the target product I-1 was 82%.

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Abstract

The invention discloses a free radical cyclization reaction method of 1, 6-diene and azoalkyl nitrile in a water phase, and relates to a high-regioselectivity free radical cyclization reaction methodof a 1, 6-diene compound and azoalkyl nitrile in a water phase without any additive. The method comprises the following steps of: adding a 1, 6-diene compound, an azo alkyl nitrile compound and waterinto a Schlenk reaction flask, and carrying out a stirring reaction at a certain temperature in an air atmosphere to obtain a cyclized product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and specifically relates to a high regioselective free radical cyclization reaction method of 1,6-diene compounds and azoalkylnitriles in an aqueous phase without any additives. Background technique [0002] In modern organic chemistry, developing practical and environmentally benign synthetic strategies is still a goal pursued by chemists. In particular, organic solvents are considered to be the main substances in the chemical transformation process, accounting for more than half of all materials used in the reaction process. Therefore, the development of organic chemical transformations in green reaction media is imminent. As we all know, chemists have put much effort into using water as an organic reaction medium due to its safety, low cost, eco-friendliness, and unique physical and chemical properties. On the other hand, achieving organic transformations without the aid of any additives i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/46C07D209/96
CPCC07D209/46C07D209/96
Inventor 刘燚魏文廷
Owner NINGBO UNIV
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