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A kind of diamine monomer containing pyrimidine and indole structure and preparation method thereof

A technology of diamine monomer and indole structure, which is applied in the field of diamine monomer and its preparation, can solve the problems of low reactivity, low recovery rate, expensive catalyst, etc., and achieve high reactivity and elongation at break High, responsive, clean and environmentally friendly

Active Publication Date: 2022-07-12
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this patent has the following problems: (1) the catalyst used in the synthesis method [RhCp*C 12 ] 2 Extremely expensive, reaching more than 1,000 yuan per gram
(2) The scope of application of the substrate of the raw material used in the synthetic method is small, causing the reactivity to become low, and the product yield obtained is lower
(3) The catalytic system used for nitro reduction in the synthesis method is active iron powder and acetic acid. The diamine compound has basic groups of amino and pyrimidinyl. The acidic catalytic system will damage the product, and it is not environmentally friendly and has low cleanliness. , the recovery rate is reduced, and the post-processing is complicated

Method used

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  • A kind of diamine monomer containing pyrimidine and indole structure and preparation method thereof
  • A kind of diamine monomer containing pyrimidine and indole structure and preparation method thereof
  • A kind of diamine monomer containing pyrimidine and indole structure and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] when R 1 for nitro, R 2 for hydrogen, R 3 for hydrogen, R 4 for nitro, R 5 , R 6 for the amino group. The specific steps of synthesis are:

[0032] (1) In a pressure-resistant reaction flask, add A-1 (240mg, 1mmol), 4-nitrophenylboronic acid (498mg, 2mmol), silver hexafluoroantimonate (34.4mg, 0.1mmol), trifluoromethanesulfonic acid Copper (362 mg, 1 mmol), catalyst [RuCl 2 (p-cymene)] 2 (12.2 mg, 0.02 mmol), 1,4-dioxane (6 mL), heated to 110° C. with magnetic stirring and reacted for 12 h. After the mixture was suction filtered through celite, the organic solvent was removed under reduced pressure, and it was separated and purified by silica gel column chromatography [V (petroleum ether):V (ethyl acetate)=10:1] to obtain a pure product with a yield of 85%. .

[0033] (2) Dissolve the above-mentioned nitro compound B-1 (361 mg, 1 mmol) in ethanol (8 mL) in an autoclave, add palladium carbon (50 mg), and H 2 (20 atm), magnetic stirring was carried ...

Embodiment 2

[0035]

[0036] when R 1 for nitro, R 2 for hydrogen, R 3 for hydrogen, R 4 for nitro, R 5 , R 6 for the amino group. The specific steps of synthesis are:

[0037] (1) In a pressure-resistant reaction flask, add A-2 (240mg, 1mmol), 3-nitrophenylboronic acid (498mg, 2mmol), silver hexafluoroantimonate (34.4mg, 0.1mmol), trifluoromethanesulfonic acid Copper (362 mg, 1 mmol), catalyst [RuCl 2 (p-cymene)]2 (12.2 mg, 0.02 mmol), 1,4-dioxane (6 mL), heated to 140° C. with magnetic stirring for 8 h. After the mixture was suction filtered through celite, the organic solvent was removed under reduced pressure, and the mixture was separated and purified by silica gel column chromatography [V (petroleum ether):V (ethyl acetate)=10:1] to obtain a pure product with a yield of 87%. .

[0038] (2) In the autoclave, the above-mentioned nitro compound B-2 (361 mg, 1 mmol) was dissolved in ethanol (8 mL), palladium carbon (50 mg) was added, and H 2 (20 atm), magnetic stirring at 78...

Embodiment 3

[0040]

[0041] when R 1 for nitro, R 2 for hydrogen, R 3 for hydrogen, R 4 for nitro, R 5 , R 6 for the amino group. The specific steps of synthesis are:

[0042] (1) In a pressure-resistant reaction flask, add A-3 (240mg, 1mmol), 4-nitrophenylboronic acid (498mg, 2mmol), silver hexafluoroantimonate (34.4mg, 0.1mmol), trifluoromethanesulfonic acid Copper (362 mg, 1 mmol), catalyst [RuCl 2 (p-cymene)] 2 (12.2 mg, 0.02 mmol), 1,4-dioxane (6 mL), heated to 140° C. with magnetic stirring for 16 h. After the mixture was suction filtered through celite, the organic solvent was removed under reduced pressure, and it was separated and purified by silica gel column chromatography [V (petroleum ether):V (ethyl acetate)=10:1] to obtain a pure product with a yield of 85%. .

[0043] (2) Dissolve the above-mentioned nitro compound B-3 (361 mg, 1 mmol) in ethanol (8 mL) in an autoclave, add palladium carbon (50 mg), and H 2 (20 atm), magnetic stirring was carried out at 90 °C...

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a diamine monomer containing pyrimidine and indole structures in the molecular structure and a preparation method thereof. The preparation method combines compound A, nitrophenyl boronate, hexafluoroantimonic acid Silver, copper triflate, catalyst [RuCl 2 (p‑cymene)] 2 Reaction in 1,4-dioxane to obtain nitro compound B; then nitro compound B is dissolved in an ethanol solvent, reacted under the conditions of palladium carbon and hydrogen, and the nitro group is reduced to an amino group to obtain a compound containing Diamine monomers C of pyrimidine and indole structures. The diamine monomer has simple structure, easily available raw materials, cheap catalyst, simple preparation method, high product yield, and environmental protection.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a diamine monomer containing pyrimidine and indole structures in a molecular structure and a preparation method thereof. Background technique [0002] Aromatic polyimide is an important special polymer material with excellent thermal stability, mechanical properties and insulating properties, and has potential application value in high-tech fields such as aerospace, petrochemical, microelectronic packaging, and solar cells. . Its most typical application is as a flexible substrate material. In the microelectronics industry, when an aromatic polyimide film is used as a substrate for a flexible printed circuit board, its coefficient of thermal expansion (CTE) needs to match the CTE value of copper (17ppm / K). There is a big difference. When the circuit board is subjected to alternating heat and cold, it will generate a large stress at the interface and cause ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C08G73/10
CPCC07D403/04C08G73/1085C08G73/1039Y02P20/584
Inventor 王亮郑子昂周春妮李鹏杰胡思前
Owner JIANGHAN UNIVERSITY
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