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Free radical cyclization reaction method based on 1,6-enynes and alcohols

A cyclization reaction and compound technology, applied in the field of free radical cyclization reaction, can solve the problems of high cost, high energy consumption, environmental pollution, etc., and achieve the effects of easy operation, high yield and wide application range

Inactive Publication Date: 2021-09-28
YANGTZE NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a free radical cyclization reaction method based on 1,6-enyne compounds and alcohol compounds, which solves the need for transition metal catalysts or high temperatures in existing preparation methods, and the existence of energy Problems such as high consumption, high cost and environmental pollution

Method used

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  • Free radical cyclization reaction method based on 1,6-enynes and alcohols
  • Free radical cyclization reaction method based on 1,6-enynes and alcohols
  • Free radical cyclization reaction method based on 1,6-enynes and alcohols

Examples

Experimental program
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Effect test

Embodiment 1

[0022]

[0023] To a Schlenk bottle was added the 1,6-enyne compound shown in 1a (36.5 mg, 0.2 mmol) and isopropanol (0.5 mL), followed by tert-butyl peroxybenzoate (TBPB, 77.6 mg, 0.4 mmol) , and then the reactor was stirred and reacted in an air atmosphere at 80°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 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. (75% yield); 1 H NMR (400MHz, DMSO-d6) δ: 7.73 (d, J = 8.0Hz, 2H), 7.38 (t, J = 7.6Hz, 2H), 7.13 (t, J = 7.2Hz, 1H), 5.22-5.17 (m,2H),4.55-4.46(m,2H),4.08(s,1H),2.04(d,J=14.0Hz,1H),1.80(d,J=14.0Hz,1H),1.21(s, 3H), 1.07(s,3H), 1.05(s,3H); 13 CNMR (100MHz, DMSO-d6) δ: 177.5, 146.9, 139.8, 129.1, 124.4, 120.1, 108.4, 69.5, 52.5, 52.2, 48.0, 31.9...

Embodiment 2

[0025] The oxidant tert-butanol peroxide (TBHP, 36.0 mg, 0.4 mmol) was used to replace tert-butyl peroxybenzoate, and the other conditions were the same as in Example 1, and the yield of the target product I-1 was 89%.

Embodiment 3

[0027] The oxidant di-tert-butyl peroxide (DTBP, 58.4mg, 0.4mmol) was used to replace tert-butyl peroxybenzoate, and the other conditions were the same as in Example 1. The yield of the target product I-1 was 62%.

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Abstract

The invention discloses a free radical cyclization reaction method based on 1,6-enynes and alcohol compounds, which belongs to the technical field of organic synthesis. The method comprises the following steps: using alcohol compounds as starting materials, Carry out cyclization reaction with 1,6-enyne compound, after the reaction is complete, post-treatment to obtain cyclization product 2-pyrrolidone compound. The method has cheap and easy-to-obtain raw materials, wide sources, stability and low toxicity, does not use any transition metal catalysts and ligands, and the reaction can be carried out in an air atmosphere with mild conditions, easy operation, no heavy metal residue in the product, and a wide range of reaction substrates. , Simple, efficient, economical and green, suitable for industrial production. At the same time, the present invention also provides an economical, practical and environmentally friendly new idea for the cyclization of alcohol radicals, expanding its application range.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a free radical cyclization reaction method based on 1,6-enyne compounds and alcohol compounds. Background technique [0002] Alcohol compounds are widely used as solvents or raw materials in industry and organic synthesis research because of their cheap, easy-to-obtain and low-toxicity characteristics. Among them, through alcohol compound hydroxyl α-C(sp 3 The direct functionalization of )-H bonds to construct C-C bonds has become a research hotspot in modern organic synthetic chemistry. [0003] In recent years, chemists have developed functional group reactions of alcohol compounds with derivatives of carboxylic acids, heteroaromatics, alkenes, and alkynes. Among them, the reaction of alcohol compounds with olefin derivatives has attracted much attention due to its simplicity and efficiency and the ability to simultaneously construct multiple chemical bonds. Zhang ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/36
CPCC07D207/36
Inventor 陈锦杨吴燕汪海英胡丽吴红谕
Owner YANGTZE NORMAL UNIVERSITY
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