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Method for efficiently synthesizing 6-alkylpyrazolo[1,5-c]quinazoline skeleton compounds under non-catalytic conditions

A skeleton compound and pyrazolo technology are applied in the field of preparation of pyrazolo[1,5-c]quinazoline compounds, and achieve the effect of good application prospect and cost reduction

Inactive Publication Date: 2020-03-20
JIANGXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

We noticed that: from most literature reports, there are relatively few reports on the synthesis of fused heterocyclic quinazoline derivatives, especially the synthesis of pyrazolo[1,5-c]quinazoline derivatives

Method used

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  • Method for efficiently synthesizing 6-alkylpyrazolo[1,5-c]quinazoline skeleton compounds under non-catalytic conditions
  • Method for efficiently synthesizing 6-alkylpyrazolo[1,5-c]quinazoline skeleton compounds under non-catalytic conditions
  • Method for efficiently synthesizing 6-alkylpyrazolo[1,5-c]quinazoline skeleton compounds under non-catalytic conditions

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0016]

[0017] In a clean 25 mL Schlenk tube, add unsubstituted quinazoline-skeleton-containing N,N- Dipolar compound (0.24 mmol) and solid 1-methyl-2-phenylnitroethylene (0.2 mmol), after N 2 After evacuating the atmosphere for 3 times, add 2 mL of DMSO as solvent, at 110 o C for 24 hours, TLC plate detection, after the reaction, the reaction solution was cooled to room temperature, the reaction solution was added with an appropriate amount of water, extracted by ethyl acetate (3 × 10 mL), the organic phase was combined and washed with anhydrous Na 2 SO 4 After drying, the organic layer was concentrated and subjected to column chromatography to obtain pure 6-methyl-5-phenylpyrazolo[1,5-c]quinazoline as a white solid with a yield of 90%.

[0018] 1 H NMR (400 MHz, CDCl 3 ) δ 9.05 (s, 1H), 8.23 ​​– 8.20 (m, 1H), 7.98 –7.68 (m, 1H), 7.77 – 7.70 (m, 2H), 7.66 – 7.43 (m, 5H), 2.66 (s, 3H ).

[0019] 13 C NMR (101 MHz, CDCl 3 ) δ 155.83, 139.98, 139.53, 135.58, 132.43, ...

example 2

[0022]

[0023] In a clean 25 mL Schlenk tube, add unsubstituted quinazoline-skeleton-containing N,N- Dipolar compound (0.24 mmol) and solid 1-methyl-2-(4-methoxyphenyl) nitroethylene (0.2 mmol), after N 2 After evacuating the atmosphere for 3 times, add 2 mL of DMSO as a solvent, at 110 o C for 24 hours, TLC plate detection, after the reaction, the reaction solution was cooled to room temperature, the reaction solution was added with an appropriate amount of water, extracted by ethyl acetate (3 × 10 mL), the organic phase was combined and washed with anhydrous Na 2 SO 4 After drying, the organic layer was concentrated and column chromatographed to obtain pure 5-(4'-methoxyphenyl)-6-methylpyrazolo[1,5-c]quinazoline, white solid, yield 60%.

[0024] 1 H NMR (400 MHz, CDCl 3 ) δ 9.04 (s, 1H), 8.24 – 8.17 (m, 1H), 7,98 –7.90 (m, 1H), 7.71 – 7.56 (m, 4H), 7.08 – 7.01 (m, 2H), 3.88 (s , 3H), 2.66(s, 3H).

[0025] 13 C NMR (101 MHz, CDCl 3 ) δ 160.02, 155.72, 140.07, 139...

example 3

[0028]

[0029] In a clean 25 mL Schlenk tube, add unsubstituted quinazoline-skeleton-containing N,N- Dipolar compound (0.24 mmol), after N 2 After evacuating the atmosphere for 3 times, add 2 mL of DMSO as a solvent, and inject 1-methyl-2-(2-chlorophenyl)nitroethylene (0.2 mmol) with a 100 μL syringe, at 110 o C for 24 hours, TLC plate detection, after the reaction, the reaction solution was cooled to room temperature, the reaction solution was added with an appropriate amount of water, extracted by ethyl acetate (3 × 10 mL), the organic phase was combined and washed with anhydrous Na 2 SO 4 After drying, the organic layer was concentrated and subjected to column chromatography to obtain pure 5-(2'-chlorophenyl)-6-methylpyrazolo[1,5-c]quinazoline, white solid, yield 70% .

[0030] 1 H NMR (400 MHz, CDCl 3 ) δ 9.07 (s, 1H), 8.24 – 8.19 (m, 1H), 8.00 –7.94 (m, 1H), 7.70 – 7.59 (m, 2H), 7.57 – 7.53 (m, 1H), 7.52 – 7.48 (m , 1H),7.47 – 7.37 (m, 2H), 2.49 (s, 3H).

[0031]...

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Abstract

The invention belongs to the technical field of organic chemistry, in particular to a method for efficiently synthesizing pyrazolo[1,5-c]quinazoline skeleton compounds under non-catalytic conditions. The structures of these compounds have been 1 H NMR, 13 C NMR, MS and other methods to characterize and confirm. The present invention uses o-nitrobenzaldehyde and triethyl orthoformate series compound reaction to make 1,3-dipole quinazoline dipole and β-nitrostyrene to react without any catalyst, and DMSO was used as the solvent, and a series of pyrazolo[1,5‑c]quinazoline derivatives were generated by the reaction at a temperature of 110 °C. This reaction can efficiently prepare pyrazolo[1,5-c]quinazolines. The method of the invention has mild reaction conditions, easy operation, greatly reduced cost compared with the previous reaction cost of 1,3-dipole quinazoline dipoles and terminal alkynes, and the reaction conditions are green and environmentally friendly, and the product has high purity and is easy to separate Purification is suitable for large-scale preparation, and because the quinazoline compound skeleton has a wide range of biological activities, it has a very good application prospect in the development of new drugs.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of pyrazolo[1,5-c]quinazoline compounds. Background technique [0002] Since quinazoline derivatives contain nitrogen atoms in their structures, quinazoline derivatives also exhibit certain characteristics of nitrogen-containing heterocyclic compounds. Quinazoline derivatives are widely used in the fields of pesticides, medicine and agricultural production because of their structural variability and high-efficiency spectral biological activity. If it has medicinal activities such as sterilization, weeding, insecticide and inhibition, it has important research and application value. For example: the fungicide fluquinazole, the acaricide fenazaquin, the anticancer drug 4-anilinoquinazoline compound Iressa, etc. It is precisely because of the special structure of quinazoline derivatives and the many Biological activity has aroused great i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 王涛邵爱龙高梦陈松涛冯海燕黄阳妃唐小丽
Owner JIANGXI NORMAL UNIV
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