Synthesis of 2,2`,6,6`-tetracarboxy-[4,4`-bipyridine]

A synthesis method, bipyridine technology, applied in the direction of organic chemistry, can solve the problems of high toxicity of oxidants, troublesome post-processing, long reaction time, etc., and achieve the effects of shortened reaction time, easy recovery, and simple separation

Active Publication Date: 2021-10-08
HUNAN UNIV OF SCI & TECH
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Problems solved by technology

Taking the synthesis of 2,2',6,6'-tetracarboxy-4,4'-bipyridine as an example, there are currently two most mature methods: one is Na-catalyzed coupling, SO 2 Oxidation method, the biggest drawback of this method is the use of SO 2 As an oxidant, the oxidant is highly toxic, the operation is cumbersome, and the post-treatment is troublesome; the second is the coupling of halogenated pyridine under the action of a noble metal catalyst. The biggest disadvantage of this method is high cost, strict anhydrous and oxygen-free treatment and long reaction time

Method used

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  • Synthesis of 2,2`,6,6`-tetracarboxy-[4,4`-bipyridine]
  • Synthesis of 2,2`,6,6`-tetracarboxy-[4,4`-bipyridine]
  • Synthesis of 2,2`,6,6`-tetracarboxy-[4,4`-bipyridine]

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Embodiment Construction

[0041]The present invention will be further described in detail below in conjunction with specific experimental examples and accompanying drawings. The target compound 2,2'-6,6'-tetracarboxy-4,4'-bipyridine and the intermediate product 2,2'-6,6'-tetramethyl-4,4'-bipyridine were detected by NMR and Validation of mass spectrometry.

[0042] The name of the target compound of the present invention is 2,2'-6,6'-tetracarboxy-4,4'-bipyridine, and its structural formula is shown in formula (1):

[0043]

[0044] Its compound synthetic train of thought route is as shown in formula (2):

[0045]

[0046] It can be seen from formula (2) that its specific synthesis is completed in three steps, wherein the coupling of the first step reaction and the air oxidation of the second step reaction are carried out continuously, so the whole synthesis is divided into two parts:

[0047] (1) Synthesis of 2,2'-6,6'-tetramethyl-4,4'-bipyridine. In the first step of coupling, under the protec...

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Abstract

The invention discloses a method for synthesizing 2,2',6,6'-tetracarboxy-4,4'-bipyridine. The method includes the synthesis of 2,2'-6,6'-tetramethyl-4,4'-bipyridine and the synthesis of 2,2',6,6'-tetracarboxy-4,4'-bipyridine, The synthesis of 2,2'‑6,6'‑tetramethyl‑4,4'‑bipyridine involves coupling and air oxidation steps. The present invention uses economical and affordable air as an oxidant to oxidize the coupling product, thereby being able to compare the existing SO in terms of reaction control, product separation and raw material recovery. 2 The oxidation method and the Pd catalyst catalysis method have absolute advantages; by adding excessive 2,6-lutidine to realize the full reaction of metal sodium and the shortening of the reaction time, the yield of the product is obviously improved.

Description

technical field [0001] The invention belongs to the fields of multifunctional coordination materials, supramolecular chemistry and membrane chemistry, and specifically relates to a method for synthesizing polycarboxy bipyridine, that is, a method for aromatizing dihydropyridine by air oxidation. Background technique [0002] Multifunctional coordination materials have attracted extensive attention due to their diversity in structure and performance. In recent years, storage materials represented by metal-organic frameworks (MOFs) and covalent organic frameworks (COFs) materials are the most popular research fields in inorganic organic materials, and belong to an important category of organic materials. MOFs and COFs are coordinated by organic ligands (or combined with metal atoms or atomic clusters) to form one-dimensional, two-dimensional or three-dimensional structures, which can be used in a wide range of fields such as molecular storage, catalysis and photochemical react...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/803
CPCC07D213/803
Inventor 周再春陈地龙刘秋华
Owner HUNAN UNIV OF SCI & TECH
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