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Method for efficiently synthetizing 6-alkylpyrazol-[1,5-c]-quinazoline skeleton compounds under no catalytic condition

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

Inactive Publication Date: 2015-05-13
JIANGXI NORMAL UNIV
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  • Summary
  • 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 synthetizing 6-alkylpyrazol-[1,5-c]-quinazoline skeleton compounds under no catalytic condition
  • Method for efficiently synthetizing 6-alkylpyrazol-[1,5-c]-quinazoline skeleton compounds under no catalytic condition
  • Method for efficiently synthetizing 6-alkylpyrazol-[1,5-c]-quinazoline skeleton compounds under no catalytic condition

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, 1...

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).

[00...

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a method for efficiently synthetizing pyrazol[1,5-c]-quinazoline skeleton compounds under no catalytic condition. The structure of the compounds is represented and confirmed with 1H NMR, 13 C NMR, MS and other methods. The method disclosed by the invention comprises the following steps: reacting 1,3-dipolar quinazoline dipoles obtained from o-nitrobenzaldehyde and a series of compounds of triethyl orthoformate with beta-nitrostyrolene under the condition of no any catalysts based on DMSO as a solvent at the temperature of 110 DEG C to generate a series of pyrazol[1,5-c]-quinazoline derivatives. By adopting the method, the pyrazol[1,5-c]-quinazoline compounds can be efficiently prepared. The method disclosed by the invention is mild in reaction conditions and simple to oeprate, the cost is greatly lowered with comparison to the cost of previous reaction between the 1,3-dipolar quinazoline dipoles and terminal alkyne, the reaction conditions are environmentally friendly, the production purity is high, separation and purification are convenient, the method is suitable for large-scale preparation, and the pyrazol[1,5-c]-quinazoline skeleton compounds have excellent application prospect in new drug research and development since the structure of quinazoline compounds has broad-spectrum biological activity.

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 Applications(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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