Synthesis method of 2-cyanoalkylsulfonyl 3,4-dihydronaphthalene compound

A kind of technology of cyanoalkylsulfonyl and synthesis method, applied in the field of synthesis of 3,4-dihydronaphthalene compounds

Active Publication Date: 2020-04-21
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis strategy of ring-opening and cyclization of MCPs by forming cyanoalkyl radicals via cyclobutanone oxime esters and sulfur dioxide sources has not been disclosed in the prior art.

Method used

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  • Synthesis method of 2-cyanoalkylsulfonyl 3,4-dihydronaphthalene compound
  • Synthesis method of 2-cyanoalkylsulfonyl 3,4-dihydronaphthalene compound
  • Synthesis method of 2-cyanoalkylsulfonyl 3,4-dihydronaphthalene compound

Examples

Experimental program
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Effect test

Embodiment 1-26

[0040] Example 1-26 Reaction condition optimization test

[0041] With the methylene cyclopropane compound shown in formula II-1, the cyclobutanone oxime ester compound shown in formula III-1 as template, with K 2 S 2 o 5 for SO 2 Sources, the influence of different reaction conditions on the yield of the target product (I-1) was discussed, and representative examples are shown in Examples 1-26.

[0042] The reaction formula is as follows:

[0043] .

Embodiment 1

[0045] In the 25mL Schlenk lock reactor, add the methylene cyclopropane compound (0.2mmol) shown in formula II, the cyclobutanone oxime ester compound (0.3 mmol, 1.5 eqiuv) shown in formula III successively, K 2 S 2 o 5 (0.4 mmol, 2equiv), photocatalyst Ru(bpy) 3 Cl 2 (5 mol %), 2,6-lutidine (0.6 mmol, 3 eqiuv) and CH 3 CN (2 mL), then under the conditions of argon atmosphere (1atm) and 5W blue LED lamp irradiation, the oil bath was heated to 80°C and stirred for 18h. The reaction raw materials were completely consumed by TLC or GC-MS, and the reaction mixture was washed with salt Washed with water, the aqueous phase was extracted with ethyl acetate (3×10 mL), the combined phases were dried over anhydrous sodium sulfate, concentrated in vacuo to obtain a residue, and the residue was separated by silica gel column chromatography (elution solvent: n-hexane Alkane / ethyl acetate=5: 1 to 2: 1) obtain the target product shown in formula I-1. Yield: 81%. Yellow solid; mp 96.2...

Embodiment 2

[0047] Replace K with DABSO (1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct) 2 S 2 o 5 , all the other conditions and operations are the same as in Example 1, and the yield of the target product of formula I-1 is 25%.

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Abstract

The invention discloses a synthesis strategy for constructing a 2-cyanoalkyl sulfonyl substituted 3,4-dihydronaphthalene compound by taking MCPs, a cyclobutanone oxime ester compound and K2S2O5 as rawmaterials through visible light catalysis, wherein two carbon-carbon sigma bonds are broken in a one-pot reaction to form a carbon-carbon bond and two carbon-sulfur bonds. According to the invention,cyanoalkyl free radicals are formed to capture SO2, and subsequently sulfonyl free radicals are formed to carry out ring-opening and cyclizing on MCPs; and the synthesis method disclosed by the invention has the advantages of mild reaction conditions, simplicity, high efficiency, easily available raw material sources, wide substrate application range and high target product yield.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing 3,4-dihydronaphthalene compounds substituted by 2-cyanoalkylsulfonyl groups. Background technique [0002] Sulfur-containing derivatives are important structural units in organic synthesis and drug synthesis. Sulfone is a useful organosulfur derivative that has been widely used in the chemical industry, agrochemicals, pharmaceuticals, organic synthesis and flame retardant materials. With the wide application of sulfones, the preparation methods of sulfones have attracted the attention of organic chemists, and many novel strategies have been established. Among them, inserting sulfur dioxide is the easiest way to synthesize sulfone, usually using DABSO [DABCO·(SO 2 ) 2 ], sodium sulfite and thiourea dioxide were used as sulfur dioxide sources to prepare sulfone. [0003] Alkyl nitrile is also an important structural unit in many...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/04C07C315/00C07C317/44C07C317/46C07D317/70
CPCC07B45/04C07C315/00C07D317/70C07C2602/10C07C317/44C07C317/46
Inventor 刘宇王巧林唐课文
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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