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A method for preparing pyrazolo[1,5-c]quinazoline skeleton compounds in copper-catalyzed aqueous phase

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

Inactive Publication Date: 2019-05-03
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A method for preparing pyrazolo[1,5-c]quinazoline skeleton compounds in copper-catalyzed aqueous phase
  • A method for preparing pyrazolo[1,5-c]quinazoline skeleton compounds in copper-catalyzed aqueous phase
  • A method for preparing pyrazolo[1,5-c]quinazoline skeleton compounds in copper-catalyzed aqueous 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, 2H...

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 2c was obtained by column chromatography using a 1:8 (EA:PE) developing solvent. 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 chemistry, and specifically relates to a copper-catalyzed aqueous phase preparation method for pyrazolo[1,5-c]quinazoline skeleton compounds. The structures of these compounds were characterized and confirmed by 1H NMR, 13C NMR, IR, MS and other methods. The present invention uses o-nitrobenzaldehyde and triethyl orthoformate series compound reaction to prepare 1,3-dipole quinazoline dipole and end group alkyne to react in aqueous phase under mild conditions, and in DBU In the case of a base, a series of pyrazolo[1,5-c]quinazoline derivatives are produced by using copper sulfate pentahydrate as a catalyst at a temperature of 70°C. This reaction can efficiently prepare pyrazolo[1,5-c]quinazolines. The method of the invention has mild reaction conditions, simple and convenient operation, low cost, few side reactions, green reaction conditions, environmental friendliness, high product purity, easy separation and purification, and can be suitable for large-scale preparation, and because quinazolines The compound skeleton has a wide range of biological activities and 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] 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 Patents(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