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A kind of synthetic method of aromatic ring pyridine compound

A synthetic method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of difficult availability of raw materials, poor atom economy, high environmental factors, etc., and achieve the effects of wide application range, simple operation, and avoiding environmental pollution

Active Publication Date: 2019-05-17
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are some synthesis methods of aromatic ring pyridine compounds, these methods often have disadvantages such as difficult to obtain raw materials, many reaction steps, poor atom economy, high environmental factors, etc., which make their application in actual production greatly restricted. limits

Method used

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  • A kind of synthetic method of aromatic ring pyridine compound
  • A kind of synthetic method of aromatic ring pyridine compound
  • A kind of synthetic method of aromatic ring pyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add 1a (0.5mmol, 60.5mg), chlorobenzene (3mL), Cu(OAc) into a 15mL reaction tube 2 (0.05 mmol, 9.1 mg), 2,2'-bipyridine (0.1 mmol, 15.6 mg), TEMPO (0.5 mmol, 78.1 mg) and 2a (0.6 mmol, 80.0 μL). After evacuating and filling with nitrogen, the reaction tube was sealed, and placed in an oil bath at 120° C. for a stirring reaction for 16 h. Stop the reaction, add 15mL of dichloromethane, then wash with water and saturated NaCl solution successively, and wash the organic phase with anhydrous MgSO 4 dry. Filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate=10 / 1) gave the target product 3a (46.6 mg, 40%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.50-7.54(m,2H),7.59-7.66(m,2H),7.81-7.83(m,1H),7.85(dd,J 1 =8.4Hz,J 2 =1.2Hz, 2H), 7.89(d, J=8.4Hz, 1H), 8.18(d, J=8.0Hz, 1H), 8.53(d, J=2.0Hz, 1H), 9.32(d, J=2.4 Hz,1H). 13 C NMR (100MHz, CDCl 3 )δ126.6, 127.6, 128.6, 129.2, 129.5, 1...

Embodiment 2

[0034] Add 1a (0.5mmol, 60.5mg), toluene (3mL), Cu(OAc) into a 15mL reaction tube 2 (0.05 mmol, 9.1 mg), 2,2'-bipyridine (0.1 mmol, 15.6 mg), TEMPO (0.5 mmol, 78.1 mg) and 2a (0.6 mmol, 80.0 μL). After evacuating and filling with nitrogen, the reaction tube was sealed, and placed in an oil bath at 120° C. for a stirring reaction for 16 h. Stop the reaction, add 15mL of dichloromethane, then wash with water and saturated NaCl solution successively, and wash the organic phase with anhydrous MgSO 4 dry. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the target product 3a (48.9 mg, 42%).

Embodiment 3

[0036] Add 1a (0.5mmol, 60.5mg), 1,4-dioxane (3mL), Cu(OAc) into a 15mL reaction tube 2 (0.05 mmol, 9.1 mg), 2,2'-bipyridine (0.1 mmol, 15.6 mg), TEMPO (0.5 mmol, 78.1 mg) and 2a (0.6 mmol, 80.0 μL). After evacuating and filling with nitrogen, the reaction tube was sealed, and placed in an oil bath at 120° C. for a stirring reaction for 16 h. Stop the reaction, add 15mL of dichloromethane, then wash with water and saturated NaCl solution successively, and wash the organic phase with anhydrous MgSO 4 dry. Filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate=10 / 1) gave the target product 3a (44.3 mg, 38%).

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Abstract

The invention discloses a synthesizing method of an aromatic pyridinopyridine compound, and belongs to the technical field of organic synthesizing. According to the technical scheme, the characteristics of the synthesizing method refers to the description. The method is simple, efficient, convenient to operate, mild in conditions, and wide in substrate applying scope.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing aromatic ring pyridine compounds. Background technique [0002] Aromatic pyridine compounds are important nitrogen-containing heterocyclic compounds, which not only have various biological and pharmacological activities such as sterilization, antihypertensive, antidepressant, antiallergic, and antitumor, but also are important raw materials for the chemical industry. In addition, they are also the structural skeleton of many natural products and widely exist in nature. Although there are some synthesis methods of aromatic ring pyridine compounds, these methods often have disadvantages such as difficult to obtain raw materials, many reaction steps, poor atom economy, high environmental factors, etc., which make their application in actual production greatly restricted. limits. In summary, it is of great application value to develop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D221/18C07D215/14C07D215/20C07D215/18C07D491/056C07D401/06C07D409/06
CPCC07D215/14C07D215/18C07D215/20C07D221/18C07D401/06C07D409/06C07D471/04C07D491/056
Inventor 范学森王泽张新迎陈光
Owner HENAN NORMAL UNIV