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A kind of synthetic method of azo compound substituted by aryl alkyl

A technology of arylalkyl and synthetic methods, which is applied in the field of synthesis of azo compounds, can solve problems such as low yield, reduced product diversity, and few types of reactants, and achieve high yield, short reaction time, and easy operation. convenient effect

Active Publication Date: 2021-03-26
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this method has some shortcomings, the reaction needs to be carried out under the condition of low temperature, the kind of reactant is few, the diversity of the product is reduced, and the yield is low

Method used

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  • A kind of synthetic method of azo compound substituted by aryl alkyl
  • A kind of synthetic method of azo compound substituted by aryl alkyl
  • A kind of synthetic method of azo compound substituted by aryl alkyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In a 5mL single-port reaction flask, add 78mg (0.3mmol) phenyldiazosulfone (1.0eq), 21.6mg 2-methyl-2-propene 1-alcohol, Fe(acac) 3 10.59mg (10mol%), PhSiH 3 64.8 mg (2.0 eq), 19.2 mg methanol. Add 3mLTHF and stir at room temperature. After about 2 hours, TLC detected that the reaction was complete, transferred and separated by column. 14mg of yellow liquid was obtained, the yield was 67%. The reaction formula is as follows:

[0041]

[0042] The physical properties and spectrogram data of the product are as follows:

[0043] Compound HRMS(ESI-TOF)m / z:[M+H] + calcd for C 10 h 15 N 2 O179.1179; found 179.1181.

[0044] In different solvent environments, the stability situation of embodiment 1 product, see Figure 5 . The solvents from left to right are acetone, ethyl acetate, tetrahydrofuran, dichloromethane, chloroform, deuterated chloroform, methanol and acetonitrile.

Embodiment 2

[0046] In a 5mL single-port reaction flask, add 52mg (0.2mmol) phenyldiazosulfone (1.0eq), 44.4mg benzyl-protected allyl alcohol, Fe(acac) 3 7.06mg (10mol%), PhSiH 3 43.2 mg (2.0 eq), 12.8 mg methanol. Add 2mL THF and stir at room temperature. After about 2 hours, TLC detected that the reaction was complete, and the product was separated by column to obtain 16.4 mg, with a yield of 50%. The reaction formula is as follows:

[0047]

[0048]The physical properties and spectral data of the product are as follows: HRMS (ESI-TOF) m / z: [M+H] + calcd for C 17 h 21 N 2 O269.1649; found 269.1636.

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Abstract

The invention discloses an arylalkyl-substituted azo compound and its preparation method and application. The preparation method comprises the following steps: in the presence of an iron catalyst and a reducing agent, aryldiazosulfone and a vinyl compound The reaction occurs in a solvent, and after the reaction is completed, the azo compound substituted by the arylalkyl group is obtained through post-treatment. In the reaction, the alkenes are inserted into HFe(III) and then decomposed, and the generated alkyl radicals attack the nitrogen-nitrogen double bond of the aryl diazosulfone, and then remove Ts to restore the nitrogen-nitrogen double bond to form the final arylalkyl Substituted azo compounds. Among them, p-toluenesulfonyl and Fe Ⅱ ‑Ln reacts to Fe Ⅲ ‑Ln, under the action of phenylsilane and methanol, Fe Ⅲ H‑Ln, enabling recycling. The preparation method can introduce various functional groups on the alkyl chain, increasing the diversity of products. At the same time, the reaction conditions are mild, the method is simple and fast, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of dye synthesis, and in particular relates to a synthesis method of arylalkyl substituted azo compounds. Background technique [0002] Arylalkyl-substituted azo compounds are a typical class of photochromic materials and important dye synthesis intermediates, which are most widely used in the printing and dyeing industry. [0003] For the synthesis of aromatic azo compounds, the traditional methods include diazo coupling reaction and Mills reaction. In the diazonium coupling reaction, the diazotization reaction of aromatic amines produces diazonium salts, and the positive ions of aromatic diazonium salts can be used as electrophiles to carry out the reaction on the aromatic ring with active aromatic compounds such as phenols and tertiary aromatic amines. Electrophilic substitution generates azo compounds (see Scheme Ⅰ). The Mills reaction is the reaction of aromatic primary amines and aromatic nitroso com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/06
CPCC07C245/06
Inventor 张岩朱钢国黄玉婷胡琪陈李琼胡雅卿
Owner ZHEJIANG NORMAL UNIVERSITY
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