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Dipyridine bridged bis-triazine compounds and preparation method thereof

A bipyridine bridge and bis-triazine technology is applied in the field of 2,2'-bipyridine bridge bis-triazine compounds, achieving the effects of mild conditions, high yield and simple process

Inactive Publication Date: 2014-01-29
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, R is a branched alkyl or cycloalkyl substituted alkyl (R is isobutyl, 3-methylbutyl, 4-methylpentyl, 3-methylhexyl, 5-methylhexyl, 2 -cyclopentyl ethyl or 2-cyclohexyl ethyl) of the synthesis and application of BTBP compounds have not been reported

Method used

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  • Dipyridine bridged bis-triazine compounds and preparation method thereof
  • Dipyridine bridged bis-triazine compounds and preparation method thereof
  • Dipyridine bridged bis-triazine compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of 6,6'-bis(5,6-diisobutyl-1,2,4-triazin-3-yl)-2,2'-bipyridine BTBP-3a

[0024] Add 2,2'-bipyridine-6,6'-diimide hydrazide (1) (0.54g, 2.0mmol), 2,7-dimethyl-4 , 5-octanedione (2a) (0.69g, 4.0mmol), 50mL tetrahydrofuran and 2mL triethylamine, magnetic stirring, heated to 65 ° C for 20 hours. The mixture was cooled to room temperature, filtered, and the filter cake was washed with 5 mL of tetrahydrofuran. The combined filtrates were removed under reduced pressure (20 mmHg) to remove volatile components. The crude product was separated by silica gel column chromatography, the eluent was dichloromethane, and the solvent was removed under reduced pressure (20mmHg) to obtain the target product BTBP-3a (0.65g, yield 60%), and its composition and molecular structure were obtained by nuclear magnetic resonance spectrum 1 H, 13 C{ 1 H} NMR and HRMS measurements were confirmed.

Embodiment 2

[0025] Example 2: Preparation of 6,6'-bis(5,6-diisobutyl-1,2,4-triazin-3-yl)-2,2'-bipyridine BTBP-3a

[0026] The reaction steps and operations were the same as in Example 1, except that the reaction time was 5 hours to obtain the target product BTBP-3a (0.47 g, yield 44%).

Embodiment 3

[0027] Example 3: Preparation of 6,6'-bis(5,6-diisobutyl-1,2,4-triazin-3-yl)-2,2'-bipyridine BTBP-3a

[0028] The reaction steps and operation are the same as in Example 1, except that the difference from Example 1 is that the reaction temperature is 20° C. to obtain the target product BTBP-3a (0.14 g, yield 13%).

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Abstract

The invention discloses seven novel 2,2'-dipyridine bridged bis-triazine compounds, particularly 6,6'-di(5,6-dialkyl-1,2,4-triazinyl-3-yl)-2,2'-dipyridine compounds with the side chain alkyl group of isobutyl, 3-methylbutyl, 4-methylamyl, 3-methylhexyl, 5-methylhexyl, 2-cyclopentylethyl or 2-cyclohexylethyl group and a preparation method thereof.2,2'-dipyridyl-6,6'-diiminohydrazide and alkyl substituted alpha-dione used as initial raw materials are heated to perform dehydration cyclization reaction for 5-24 hours by using tetrahydrofuran / triethylamine as a reaction solvent, thereby obtaining the seven 6,6'-di(5,6-dialkyl-1,2,4-triazinyl-3-yl)-2,2'-dipyridine compounds. The method has the characteristics of mild conditions, accessible raw materials, high target product yield and the like, and is simple to operate.

Description

technical field [0001] The present invention relates to seven novel 2,2'-bipyridyl bridged bis-triazine compounds, that is, the side chain alkyl is isobutyl, 3-methylbutyl, 4-methylpentyl, 3-methylhexyl , 5-methylhexyl, 2-cyclopentylethyl or 2-cyclohexylethyl 6,6'-di(5,6-dialkyl-1,2,4-triazin-3-yl) -2,2'-bipyridine (abbreviated as BTBP) and a preparation method thereof. These seven new 6,6'-diketones were synthesized by the dehydration and cyclization reaction of 2,2'-bipyridine-6,6'-diimide hydrazide with alkyl-substituted α-diketones under heating conditions. (5,6-Dialkyl-1,2,4-triazin-3-yl)-2,2'-bipyridine compounds. The method is characterized in that the raw materials are readily available, the process is simple, the conditions are mild, and the yield of the target product is high. technical background [0002] 6,6’-bis(5,6-dialkyl-1,2,4-triazin-3-yl)-2,2’-bipyridine (BTBP) is an important organic compound. This type of compound has excellent coordination ability to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/14
Inventor 余正坤王连弟
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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