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Pyridine alkyne precursor and synthesis method thereof

A synthetic method and technology of pyridyne, applied in the field of pyridyne precursor and its synthesis, to achieve good solubility, stable chemical properties, and broad application prospects

Inactive Publication Date: 2019-06-04
CHONGQING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the problem existing in the existing pyridyne precursors, the problem to be solved in the present invention is to provide a pyridyne precursor and a synthesis method thereof, the pyridyne precursor has double nucleophilic functions at the 3 and 5 positions of the pyridine ring chemical reaction performance

Method used

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  • Pyridine alkyne precursor and synthesis method thereof
  • Pyridine alkyne precursor and synthesis method thereof
  • Pyridine alkyne precursor and synthesis method thereof

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Embodiment

[0023] The aryne precursor of the present invention is composed of five steps:

[0024] The first step, the synthesis of 4-bromo-3,5-dimethoxypyridine

[0025] The structural formula 2 of 4-bromo-3,5-dimethoxypyridine is as follows:

[0026] The synthetic reaction process of this 4-bromo-3,5-dimethoxypyridine:

[0027]

[0028] 3,5-dimethoxypyridine (1.4g, 10mmol, 1.0equiv.) of structural formula 1 was dissolved in tetrahydrofuran

[0029]

[0030] (30mL), cooled to -78°C, added n-butyllithium (n-BuLi) (2.5M n-hexane solution, 4.8mL, 12mmol, 1.2equiv.), stirred for five minutes, added 1,1,2,2 -Tetrabromoethane (1.75mL, 15mmol, 1.5equiv.), returned to room temperature. Post-treatment and purification by silica gel column chromatography yielded 1.14 g of 4-bromo-3,5-dimethoxypyridine 2 with a yield of 52%.

[0031] The second step, the synthesis of 4-bromo-3,5-dihydroxypyridine

[0032] The structural formula 3 of 4-bromo-3,5-dihydroxypyridine is as follows:

[0033]...

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Abstract

The invention discloses a pyridine alkyne precursor and a synthesis method thereof. The pyridine alkyne precursor has a structure as shown in A, the synthesis method of the pyridine alkyne precursor comprises the following five steps: the synthesis of 4-bromo-3,5-dimethoxy pyridine, the synthesis of 4-bromo-3,5-dihydroxypyridine, the synthesis of 4-dimethyl-tert-butylsilyl-5-dimethyl-tert-butyl siloxy-3-hydroxypyridine, the synthesis of 4-dimethyl-tert-butylsilyl-3,5-dihydroxypyridine, and the synthesis of the pyridine alkyne precursor A. The technical effects are as follows: first, the pyridine alkyne precursor has the property of performing a dinucleophilic functionalization reaction at the 3 and 5 positions of the pyridine ring, and the property has broad application prospects in the fields of organic synthesis and drug synthesis; and secondly, the pyridine alkyne precursor is simple in synthesis method and can be prepared in large quantities.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a pyridyne precursor and a synthesis method thereof. Background technique [0002] The structure with pyridine ring as the core skeleton widely exists in biologically active natural compounds and drug molecules. Therefore, the development of efficient synthesis methods for polysubstituted pyridine derivatives is one of the focuses of synthetic organic chemistry research. As a highly active intermediate, pyridyne can introduce two functional groups on the pyridine ring at the same time, so it has a wide range of applications in the fields of natural product synthesis and pharmaceuticals. [0003] However, due to the characteristics of the carbon-carbon triple bond in pyridyne, only one nucleophilic functional group and one electrophilic functional group can be introduced at the 2,3 or 3,4 positions of the pyridine ring when nucleophilic reactions occur. It i...

Claims

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Application Information

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IPC IPC(8): C07F7/08C07F7/10
Inventor 李杨陈頔
Owner CHONGQING UNIV
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