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Methylene bridged 1,8-naphthyridine ligand and copper (i) complex, preparation method and application

A methylene bridge, naphthyridine copper technology, applied in the field of chemistry, can solve problems such as high cost, toxic and harmful heavy metal residues, etc., and achieve the effect of shortening the reaction process and simplifying the raw materials

Inactive Publication Date: 2018-11-20
HONGHE COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the past ten years, the classic noble metal-catalyzed carbon-hydrogen bond activation has made great progress, but the toxic and harmful heavy metal residues and high cost have been difficult to solve

Method used

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  • Methylene bridged 1,8-naphthyridine ligand and copper (i) complex, preparation method and application
  • Methylene bridged 1,8-naphthyridine ligand and copper (i) complex, preparation method and application
  • Methylene bridged 1,8-naphthyridine ligand and copper (i) complex, preparation method and application

Examples

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Embodiment

[0043] 1. Synthesis of methylene bridged 1,8-naphthyridine ligand and copper (I) complex:

[0044] 1) Synthesis of 2-methyl-4-R 1 -7-Acetamido-1,8-naphthyridine:

[0045] Add 7-amino-2,4-dimethyl-1,8-naphthyridine or 7-amino-2-methyl-1,8-naphthyridine (4.0 g, 23.1 mmol) into a 100 mL round bottom flask, add 15mL of acetic anhydride, the mixture was refluxed for 2h under the protection of nitrogen, and the reaction liquid was cooled to precipitate yellow crystals, which were filtered to obtain 7-acetamido-2,4-methyl-1,8-naphthyridine or 7-acetamido-2-methyl -1,8-naphthyridine product is directly used in the following reaction;

[0046] 2) No catalyst SP 3Synthesis of methylene bridged 1,8-naphthyridine ligands by C—H activation:

[0047] Dissolve 0.35g (2.33mmol) o-aldehyde benzoic acid in 30mL N,N-dimethylformamide, raise the temperature to 150°C under nitrogen protection, and then add 0.50g (2.32mmol) 7-acetamido-2,4 -Dimethyl-1,8-naphthyridine and continue to reflux for...

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Abstract

The invention discloses a methylene bridging 1,8-naphthyridine ligand and copper (I) complex, a preparing method and an application. The molecular formula of the methylene bridging 1,8-naphthyridine ligand and copper (I) complex is shown in the specification, wherein R1 is hydrogen or methyl. The methylene bridging 1,8-naphthyridine ligand and copper (I) complex is the first complex obtained in the mode that an activation reaction is carried out through a SP3C-H key under the condition that a catalyst is free so far, and it is firstly achieved that a C-C key is activated and constructed through the catalyst-free SP3C-H key. The copper (I) complex can be used as a catalyst of a coupling reaction between aryl halide and imidazole compound C-N, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of chemistry and relates to naphthyridine complexes. More specifically, it relates to a methylene bridged 1,8-naphthyridine ligand and a copper (I) complex, a preparation method and an application. Background technique [0002] The C—H bond is the simplest and most common functional group in organic compounds. The chemical synthesis based on the C—H bond activation strategy can simplify the raw materials, shorten the reaction process, and realize the target product that is difficult to prepare by conventional methods. It is the most economical and concise , the most efficient way, in line with the development trend of modern green synthetic chemistry, so the synthesis methodology of forming C—C, C—X bonds through the activation of C—H bonds has been widely concerned by organic chemists. However, due to the high bond energy of the C—H bond, low polarity, difficult activation, and low reactivity, it is very d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07F1/08B01J31/22C07D233/58C07D233/56C07D233/60C07D401/04
CPCB01J31/183B01J2231/4283B01J2531/0213B01J2531/16C07D233/56C07D233/58C07D233/60C07D401/04C07D471/04C07F1/005
Inventor 苟高章汪学全陈雪冰严和平洪涌刘卫
Owner HONGHE COLLEGE
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