1,6-eneyne compound and alcohol compound based free radical cyclization reaction method
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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 effect of easy operation, high yield and obvious advantages
Inactive Publication Date: 2019-07-26
YANGTZE NORMAL UNIVERSITY
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[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
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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, 36.0mg, 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 89%.
Embodiment 3
[0027] The oxidant di-tert-butyl peroxide (DTBP, 58.4 mg, 0.4 mmol) 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 belongs to the technical field of organic synthesis and discloses a 1,6-eneyne compound and alcohol compound based free radical cyclization reaction method. The method includes steps: taking an alcohol compound as a starting raw material, subjecting to cyclization reaction with a 1,6-eneyne compound under the action of an oxidant, and after complete reaction, performing aftertreatment to obtain a cyclization product namely a 2-pyrrolidone compound. The method has advantages that raw materials are cheap, easy to acquire, extensive in source, stable and low in toxicity, consumptionof any transition metal catalysts and ligands is avoided, the reaction can be carried out in an air atmosphere and is mild in condition and easy in operation, the product is free of heavy metal residues, and the method has advantages of extensive reaction substrate applicable range, simple, efficient, economical and green and is suitable for industrial production. In addition, an economical, practical, green and environmental-friendly novel idea is provided for alcohol free radical cyclization, and an application range is expanded.
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 ...
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