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Polysubstituted pyridine derivative and preparation method thereof

A derivative and multi-substitution technology, which is applied in the field of multi-substituted pyridine derivatives and its preparation, can solve the problems of single preparation method of multi-substituted pyridine, and achieve the effects of reducing costs, avoiding heavy metal pollution, and high reaction efficiency

Inactive Publication Date: 2021-12-17
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The technical problem to be solved by the present invention is that the preparation method of polysubstituted pyridine in the prior art is single

Method used

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  • Polysubstituted pyridine derivative and preparation method thereof
  • Polysubstituted pyridine derivative and preparation method thereof
  • Polysubstituted pyridine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0216] Example 1: 7-phenyl-2,2-dimethyl-4H-[1,3]-dioxino[5,4-c]pyridin-4-one, the yield is 75%.

[0217]

[0218] 1 H NMR (400MHz, CDCl 3 )δ9.13(s,1H),8.02–8.00(m,2H),7.49–7.46(m,3H),7.30(s,1H),1.78(s,6H). 13 C NMR (100MHz, CDCl 3 ): δ164.36, 162.83, 159.67, 151.74, 137.76, 130.63, 129.02, 127.45, 108.42, 108.13, 107.68, 26.06.

Embodiment 2

[0219] Example 2: 7-phenyl-2,2-dimethyl-4-oxo-4H-[1,3]-dioxino[5,4-c]pyridine-8-carbaldehyde, yield 10 %.

[0220]

[0221] 1 H NMR (400MHz, CDCl 3 )δ9.93(s,1H),9.27(s,1H),7.61–7.57(m,2H),7.57–7.52(m,3H),1.85(s,6H). 13 C NMR (100MHz, CDCl 3 )δ188.34, 168.50, 161.96, 158.94, 153.90, 136.72, 130.96, 130.55, 128.92, 119.03, 108.73, 108.69, 26.19.

Embodiment 3

[0222] Example 3: 7-(4-chlorophenyl)-2,2-dimethyl-4H-[1,3]-dioxino[5,4-c]pyridin-4-one, yield 70 %.

[0223]

[0224] 1 H NMR (400MHz, CDCl3 )δ9.13(s,1H),7.97(d,J=8.1Hz,2H),7.46(d,J=8.1Hz,2H),7.28(s,1H),1.79(s,6H). 13 C NMR (100MHz, CDCl 3 )δ163.03, 163.00, 159.55, 151.85, 137.02, 136.17, 129.33, 128.79, 108.64, 108.07, 107.86, 26.13.

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Abstract

The invention discloses a polysubstituted pyridine derivative and a preparation method thereof. Specifically, the preparation method of the polysubstituted pyridine derivative is any one of the following schemes: according to the scheme I: in the presence of a halogenating reagent and / or sulfonic anhydride, a compound 1 and a compound 2 are subjected to a cyclization reaction as shown in the description to obtain a compound 2; according to the scheme 2, in the presence of carboxylic acid anhydride and / or sulfonic anhydride and in the presence of one or more of BF3.Et2O, CF3SO2OAg and AgBF4, the compound 1 and R3C(OR6) 3 are subjected to a cyclization reaction as shown in the description to obtain a compound 2; and according to the scheme 3, in the presence of carboxylic acid anhydride and / or sulfonic anhydride and in the presence of a solvent, the compound 1 and R3COCl are subjected to a cyclization reaction as shown in the description to obtain a compound 2. The preparation method is mild in condition and wide in universality, and does not need to use a high-toxicity reagent.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a polysubstituted pyridine derivative and a preparation method thereof. Background technique [0002] Multi-substituted pyridine compounds are a very important class of nitrogen heterocyclic compounds, which have great application value as chemical industry raw materials and organic synthesis building blocks. Multi-substituted pyridines have been widely used in various production and research fields such as medicine, pesticides, functional materials, fine chemical catalysis, and coordination chemistry. For a long time, these compounds have been the focus of attention and research hotspots of chemists. So far, chemists have developed many effective methods for synthesizing polysubstituted pyridines, but many methods also have severe reaction conditions, difficult preparation of reaction raw materials, single types of products synthesized by reactions, and difficult fur...

Claims

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Application Information

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IPC IPC(8): C07D491/056C07D519/00C07D319/06C07D405/06C07D405/14
CPCC07D491/056C07D519/00C07D319/06C07D405/06C07D405/14Y02P20/584
Inventor 张洪彬魏凯孙玉翠李瑞赵静峰陈文何严萍羊晓东
Owner YUNNAN UNIV
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