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Nitrogenous aromatic heterocyclic nitro compound as well as preparation method and application thereof

A technology for nitro compounds and aromatic heterocycles, which is applied in the field of nitrogen-containing aromatic heterocycle nitro compounds and their preparation, and can solve the problems of limited types of synthetic heterocycles, lengthy synthetic routes, complicated operations, etc.

Active Publication Date: 2021-06-04
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the methods for synthesizing nitrogen-containing aromatic heterocyclic nitro compounds in the prior art generally have the disadvantages of lengthy synthetic routes, complicated operations, and limited scope of substrate application. At the same time, the types of heterocyclic rings synthesized are limited and single

Method used

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  • Nitrogenous aromatic heterocyclic nitro compound as well as preparation method and application thereof
  • Nitrogenous aromatic heterocyclic nitro compound as well as preparation method and application thereof
  • Nitrogenous aromatic heterocyclic nitro compound as well as preparation method and application thereof

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preparation example Construction

[0041] The present invention also provides a method for preparing the nitrogen-containing aromatic heterocyclic nitro compound described in the above technical scheme, comprising the following steps:

[0042] a) Under an inert atmosphere, the compound of the structure shown in the formula (I), the compound of the structure shown in the formula (II), a metal catalyst, an alkali metal compound and a solvent are mixed and reacted to obtain a nitrogen-containing aromatic heterocyclic nitro compound ;

[0043]

[0044] In formula (I), R1 is selected from H, C1~C18 aliphatic hydrocarbons or C1~C18 aromatic hydrocarbons;

[0045]

[0046] In formula (II), X, Y, and Z are independently selected from C or N, and at least two of X, Y, and Z are C; R2 is selected from Cl, Br, I, OH, OAc, OMs or OTf; R3 is selected from Cl, Br, I, OH, OAc, OMs, OTf, NH 2 or NO 2 .

[0047] In the present invention, the inert atmosphere is preferably a nitrogen atmosphere or an argon atmosphere. ...

Embodiment 1

[0090] (1) Under nitrogen protection, 4-nitrophenylboronic acid pinacol ester (0.11mol, 27.40g), 2,5-dichloropyridine (0.05mol, 7.40g), 1,3-bis(di Phenylphosphinopropane) nickel dichloride (0.003mol, 1.63g), anhydrous potassium carbonate (0.5mol, 69.10g), 80mL toluene and 80mL deionized water were added to a 250mL round-bottomed flask in sequence, and the reaction system was heated at 90°C Stir under reflux, TLC monitoring until 2,5-dichloropyridine completely disappears, stop the reaction, cool to room temperature, a large amount of solids precipitate out, filter the solids and wash them with deionized water, toluene and methanol for several times, and then dry them in vacuum. The crude product was obtained; after the crude product was purified, 13.97 g of a brown solid was finally obtained, namely 2,5-bis(4-nitrophenyl)pyridine, with a yield of 87%.

[0091] 1 H NMR (400MHz, DMSO-d 6 ,100℃)δ9.12(d,J=2.4Hz,1H),8.39(d,J=8.8Hz,2H),8.31(d,J=8.4Hz,5H),8.19(d,J=8.4Hz ,1H),8.06(...

Embodiment 2

[0099] (1) Under nitrogen protection, 4-nitrophenylboronic acid (0.11mol, 18.36g), 5-bromo-2-chloropyrimidine (0.05mol, 9.67g), bis(triphenylphosphine) dichloride Palladium (0.002mol, 1.40g), anhydrous potassium carbonate (0.5mol, 69.10g), 80mL toluene and 80mL deionized water were successively added in a 250mL Schlenk bottle, and the reaction system was stirred and refluxed at 100°C, and TLC monitored until 5- Bromo-2-chloropyrimidine completely disappeared, the reaction was stopped, and a large amount of solids precipitated after cooling to room temperature. After the solids were filtered and washed with deionized water, toluene and methanol several times in sequence, the crude product was obtained by vacuum drying; the crude product was purified , and finally obtained 13.32 g of a yellow solid, namely 2,5-bis(4-nitrophenyl)pyrimidine, with a yield of 83%.

[0100] 1 H NMR (400MHz, DMSO-d 6 ,100℃)δ9.34(s,2H),8.66(d,J=8.8Hz,2H),8.33(d,J=8.8Hz,4H),8.13(d,J=8.8Hz,2H).

[010...

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Abstract

The invention provides a nitrogen-containing aromatic heterocyclic nitro compound as well as a preparation method and application thereof. The nitrogenous aromatic heterocyclic nitro compound has a structure as shown in a formula (III), wherein X, Y and Z are independently selected from C or N, and at least two of X, Y and Z are C; and R0 is selected from NO2 and NH2. Compared with the prior art, the nitrogenous aromatic heterocyclic nitro compound provided by the invention can be used for synthesizing nitrogenous aromatic heterocyclic diamine, so that the whole synthesis route is simple, the treatment is convenient, the substrate application range is wide, the yield is higher, and the compound is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of polymer materials, and more specifically relates to a nitrogen-containing aromatic heterocyclic nitro compound and its preparation method and application. Background technique [0002] Aromatic nitro compounds are an important class of organic synthesis intermediates, which can be widely used as important chemical raw materials and reagents in the fields of dyes, medicines, explosives, and polymer materials. Especially nitrogen-containing aromatic heterocyclic nitro compounds have extremely important applications in the field of polymer materials. Specifically, the polyamide and polyimide materials prepared by using nitrogen-containing aromatic heterocyclic nitro compounds as raw materials and reducing them to aromatic heterocyclic diamines as polymerized monomers usually show better high and low temperature resistance, Chemical resistance, excellent mechanical properties and bonding properties are super...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07D239/26C07D237/08C07D241/12C07D213/73C07D213/61C07D213/74C07D239/30C07D239/42C07D237/12C07D237/20C07D241/16C07D241/20
CPCC07D213/38C07D239/26C07D237/08C07D241/12C07D213/73C07D213/61C07D213/74C07D239/30C07D239/42C07D237/12C07D237/20C07D241/16C07D241/20
Inventor 邱雪鹏鲍峰戚福玲董志鑫代学民姚海波蔡艳春
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI