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Method for preparing pyrazolo [1, 5-c] quinazoline skeleton compounds by copper catalysis in water phase

A technology for the preparation of skeleton compounds and aqueous phase, which is applied in the field of preparation of pyrazolo[1,5-c]quinazoline compounds, which can solve the problems of long reaction time, numerous steps, harsh reaction conditions, etc., and achieve easy operation , wide application range, less side effects

Inactive Publication Date: 2014-09-17
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, most of the literature reports that there are many steps in the synthesis of pyrazolo[1,5-c]quinazoline derivatives, the reaction time is long, and the reaction conditions are harsh.

Method used

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  • Method for preparing pyrazolo [1, 5-c] quinazoline skeleton compounds by copper catalysis in water phase
  • Method for preparing pyrazolo [1, 5-c] quinazoline skeleton compounds by copper catalysis in water phase
  • Method for preparing pyrazolo [1, 5-c] quinazoline skeleton compounds by copper catalysis in water phase

Examples

Experimental program
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Effect test

example 1

[0019]

[0020] Unsubstituted quinazoline N,N-dipolar compound A (0.2mmol) and 10mmol% CuSO 4 ·5H 2 O was placed in a 25mL Schlenk tube, under nitrogen protection, phenylacetylene (0.4mmol) and DBU (2.0equiv) were added at room temperature. After 12 hours of reaction, TLC tracked and detected that the reaction was complete. After the reaction, the reaction solution was cooled to room temperature. The reaction solution was extracted with ethyl acetate (3×10mL), and the organic phases were combined with MgSO 4 After drying, spin the solvent under reduced pressure with a rotary evaporator, concentrate the reaction solution and separate it by column chromatography with a 1:8 (EA:PE) developing solvent to obtain the corresponding 2-phenyl-pyrazolo[1,5-c ] quinazoline 2a , white solid, yield 80%, m.p.: 155-156 o c.

[0021] 1 H NMR (400 MHz, CDCl 3 ) : δ(ppm) 9.09 (s, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.94-7.97 (m, 3H), 7.60 (m, 2H), 7.46 (d, J = 8.4 Hz, 2H), 7.21 (s, 1H)....

example 2

[0027]

[0028] unsubstituted quinazoline N,N- Dipolar Compound A (0.2mmol) and 10mmol% CuSO 4 ·5H 2 O was placed in a 25mL Schlenk tube, and p-methoxyphenylacetylene (0.4mmol) and DBU (2.0equiv) were added at room temperature under nitrogen protection. After 12 hours of reaction, TLC tracked and detected that the reaction was complete. After the reaction, the reaction solution was After cooling to room temperature, the reaction solution was extracted with ethyl acetate (3×10 mL), and the combined organic phases were washed with MgSO 4 After drying, use a rotary evaporator to spin dry the solvent under reduced pressure. After concentrating the reaction solution, the corresponding 2-(4-methoxy-phenyl)-pyrazolo[1,5-c]quinazoline was separated by column chromatography with 1:8 (EA:PE) developing solvent 2b , white solid, yield 73%, m.p.: 145-147 o c.

[0029] 1 H NMR (400 MHz, CDCl 3 ) : δ(ppm) 9.09 (s, 1H) ,8.05 (d, J = 7.6 Hz, 1H), 7.93-7.96 (m, 3H), 7.60-7.66 (m,...

example 3

[0033]

[0034] unsubstituted quinazoline N,N- Dipolar Compound A (0.2mmol) and 10mmol% CuSO 4 ·5H 2 O is placed in a 25mL Schlenk tube, under nitrogen protection, p-bromophenylacetylene (0.4mmol) and DBU (2.0equiv) are added at room temperature. After 12 hours of reaction, TLC tracking detects that the reaction is complete. After the reaction, the reaction solution is cooled to At room temperature, the reaction solution was extracted with ethyl acetate (3×10 mL), and the combined organic phases were washed with MgSO 4 After drying, use a rotary evaporator to spin dry the solvent under reduced pressure. After concentrating the reaction solution, the corresponding 2-(4-bromo-phenyl)-pyrazolo[1,5-c]quinazoline was separated by column chromatography with 1:8 (EA:PE) developing solvent 2c , white solid, yield 79%, m.p.: 216-218 o c.

[0035] 1 H NMR (400 MHz, CDCl 3 ) : δ(ppm) 9.10 (s, 1H), 8.06 (d, J = 7.8Hz, 1H), 7.96 (d, J = 8.2 Hz, 1H), 7.89 (d, J = 8.6 Hz, 2H...

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Abstract

The invention belongs to the technical field of organic chemical, and in particular relates to a method for preparing pyrazolo [1, 5-c] quinazoline skeleton compounds by copper catalysis in water phase. The structure of the compound is characterized and is confirmed by the methods of 1HNMR, 13CNMR, IR, MS and the like. The method is as follows: 1, 3-dipolar quinazoline dipole prepared by reaction of o-nitrobenzaldehyde, triethyl orthoformate and a series of compounds reacts with terminal alkyne under mild conditions in the water phase, and a series of pyrazolo [1, 5-c] quinazoline derivatives can be prepared by reaction at the temperature of 70 DEG C under the conditions of using copper sulfate pentahydrate as a catalyst and DBU (diazabicyclo) as an alkali. The method can effectively prepare the pyrazolo [1, 5-c] quinazoline skeleton compounds. The method has the advantages of mild reaction condition, simple operation, low cost, less side reaction, green and environmentally friendly reaction conditions, high purity of product, and easy separation and purification, and can be suitable for large scale preparation, and due to broad spectrum biological activity, the quinazoline skeleton compounds have the very good application prospect in the research and 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] Organic nitrogen-containing heterocyclic compounds, which have good biological activity and widely exist in nature, are a very important class of compounds. Since quinazoline derivatives contain nitrogen atoms in their structures, quinazoline derivatives also exhibit certain characteristics of nitrogen-containing heterocyclic compounds. Due to their structural variability and high-efficiency and broad-spectrum biological activity, quinazoline derivatives are widely used in the fields of pesticides, medicine and agricultural production (Gao Yuanlei; Xiong Qizhong; An Rui; Bao Xiaoping , organic chemistry 2011, 1529-1537). If it has medicinal activities such as sterilization, weeding, insecticide and inhibition, it has important research and application value. For e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D491/147
CPCC07D487/04C07D491/147
Inventor 王涛唐小丽顾成浩李柔
Owner JIANGXI NORMAL UNIV
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