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Synthesis method of 3-methylsulfonyl substituted nitrogen heterocyclic compound
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The technology of a methanesulfonyl group and a synthesis method is applied in the field of synthesis of 3-methanesulfonyl-substituted nitrogen heterocyclic compounds, can solve the problems such as difficulty in obtaining reaction raw materials, and achieves wide application range, simple operation, and simple and easy-to-obtain reaction raw materials. Effect
Active Publication Date: 2021-01-29
HENAN NORMAL UNIV
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At present, the synthesis of methylsulfonyl-substituted nitrogen heterocycles is generally prepared through the substitution reaction of substituted nitrogen heterocycles with sodium methylthiolate. The disadvantage of this method is that it often needs to be completed in multiple steps and the reaction raw materials are not easy to obtain.
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Embodiment 1
[0011]
[0012] 1a (0.2mmol, 32mg), acetonitrile (1mL), sodium metabisulfite (1mmol, 190mg), ferricchloride (0.04mmol, 6mg), dicumyl peroxide (DCP, 0.6mmol, 162mg ) and DABCO (0.4mmol, 45mg), stirred the reaction at 140°C for 2h under air atmosphere, then quenched the reaction by adding 10mL saturated sodiumchloride solution, extracted with dichloromethane (10mL×3), combined the organic phases, anhydrous Na2SO4 dried. Filtered, spin-dried, separated by silica gel column (petroleumether / ethyl acetate=2 / 1, v / v) to obtain product 2a (29 mg, 61%) as a yellow solid. The characterization data of this compound are as follows: m.p.:96-97°C. 1 HNMR (400MHz, CDCl 3 )δ: 2.08-2.11(m, 2H), 2.49(t, J=6.0Hz, 2H), 2.93(s, 3H), 3.63(t, J=5.6Hz, 2H), 7.05-7.10(m, 3H ),7.34(t,J=8.0Hz,2H),7.70(s,1H). 13 C NMR (150MHz, CDCl 3 )δ: 20.4, 21.2, 42.2, 45.9, 107.2, 117.8, 123.5, 129.5, 139.7, 145.3. MS: m / z 238 [M+H] + .
[0016] 1a (0.2mmol, 32mg), acetonitrile (1mL), sodium metabisulfite (1mmol, 190mg), ferrous chloride (0.04mmol, 5mg), dicumyl peroxide (DCP, 0.6mmol, 162mg) and DABCO (0.4mmol, 45mg), stirred the reaction at 140°C for 2h under air atmosphere, then added 10mL saturated sodium chloride solution to quench the reaction, extracted with dichloromethane (10mL×3), combined the organic phases, without water and sodium sulfate to dry. It was filtered, spin-dried, and separated by silica gel column (petroleumether / ethyl acetate=2 / 1, v / v) to obtain product 2a (27 mg, 57%) as a yellow solid.
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Abstract
The invention discloses a synthetic method of a 3-methylsulfonyl substituted nitrogenheterocyclic compound, and belongs to the technical field of organic synthesis. According to the technical scheme,the preparation method is characterized by comprising the following steps: dissolving a saturated cyclic amine compound, pyrosulfite and methyl-containing peroxide into a solvent, adding a catalyst and alkali into a reaction system, and reacting at 100-140 DEG C in an air atmosphere to obtain a target product, namely the 3-methylsulfonyl substituted nitrogenheterocyclic compound. The target product 3-methylsulfonyl substituted nitrogenheterocyclic compound is synthesized by carrying out a one-pot multi-component cascade reaction on the saturated cyclic amine compound, the pyrosulfite and the methyl peroxide-containing compound which are simple, convenient and easy to obtain, and the method has the advantages of simplicity and convenience in operation, mild conditions, wide substrate application range and the like, and is suitable for industrial production.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-methylsulfonyl substituted nitrogen heterocyclic compounds. Background technique [0002] Substituted nitrogen heterocyclic compounds are important structural units of many natural products and drugs. On the other hand, sulfonyl-substituted compounds are not only commonly found in the structures of biologically active compounds, but sulfonyl groups can also be transformed into other different target functional groups through different unit reactions. Among them, based on the "methylation" effect, the synthesis of methylsulfonyl-substituted compounds is of great significance in the field of chemical biology. The methylsulfonyl-substituted nitrogen-heterocyclic compounds with both methylsulfonyl and nitrogen-heterocyclic structural units are of great research value in the field of organic and pharmaceutical synthesis. At present, the ...
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