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Preparation method of one-class 1,3-dipole quinazoline compound

A technology for dipolar quinazoline and compound is applied in the field of preparation of 1,3-dipolar quinazoline compounds, which can solve the problems of low pesticide activity and the like, and achieves a wide range of application, mild reaction conditions and few side reactions. Effect

Inactive Publication Date: 2013-06-26
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through our literature tracking in recent decades, we found that there are many reports on quinazoline compounds in terms of synthesis methods and pharmacological activities, but there are very few reports on pesticide activities.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0017] Take o-aminobenzaldehyde (0.1mol) and add it to a 100ml flask, then add K 2 CO 3 (0.1mol), then add ethanol as a solvent, then add hydroxylamine hydrochloride (0.12mol), stir at 20°C for 2 hours to obtain anthranilaldoxime, filter with suction, recrystallize from ethanol, dry, and get anthranilaldoxime ( Add (0.1mol) into the reaction flask, add (0.5mol) triethyl orthoformate, add a catalytic amount (10%) of glacial acetic acid, the oil bath is about 70°C, a large amount of yellow solid appears, continue to stir for one hour until the end of TLC detection , adding anhydrous diethyl ether and stirring, suction filtration, and recrystallization from acetonitrile to obtain the corresponding 1,3-dipolar quinazoline oxide as a yellow solid with a yield of 85%. mp: 155-156 o C; IR (KBr, υ / cm -1 ): 1861, 1703, 1567, 1331, 1193, 995; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.66-7.76(m, 2H), 7.85-7.91(m, 2H), 9.01(s, 1H); 13 C NMR (100 MHz, CDCl 3 ): 124.5, 125.5, 129.0, 13...

example 2

[0019] Take 2-amino-5-chlorobenzaldehyde (0.1mol) into a 100ml flask, then add K 2 CO 3 (0.1mol), then add ethanol as a solvent, then add hydroxylamine hydrochloride (0.12mol), stir at 20°C for 2 hours to obtain 2-amino-5-chlorobenzaldehyde oxime, filter with suction, recrystallize from ethanol, dry, and take 2 -Amino-5-chlorobenzaldehyde oxime (0.1mol) was added to the reaction flask, and (0.5mol) triethyl orthoformate was added, and a catalytic amount (10%) of glacial acetic acid was added, and the oil bath was about 70°C, and a large amount of yellow appeared. Solid, continue to stir for one hour until the end of TLC detection, add anhydrous ether to stir, filter with suction, recrystallize from acetonitrile to obtain the corresponding 6-chloro-1,3-dipolar quinazoline oxide, yellow solid, yield 72% . mp: 230-232℃; IR (KBr, υ / cm -1 ): 1984, 1859, 1722, 1687, 1477, 1186; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 6.76(s, 1H), 6.97(s,2H), 9.03(m,1H), 9.15(s,1H); 13 C NMR (10...

example 3

[0021] Take 2-amino-5-bromobenzaldehyde (0.1mol) into a 100ml flask, then add K 2 CO 3 (0.1mol), then add ethanol as a solvent, then add hydroxylamine hydrochloride (0.12mol), stir at 20°C for 2 hours to obtain 2-amino-5-bromobenzaldehyde oxime, filter with suction, recrystallize from ethanol, dry, and take 2 -Amino-5-bromobenzaldehyde oxime (0.1mol) was added to the reaction flask, and (0.5mol) triethyl orthoformate was added, and a catalytic amount (10%) of glacial acetic acid was added, and the oil bath was about 70°C, a large amount of yellow appeared Solid, continue to stir for one hour until the end of TLC detection, add anhydrous ether to stir, filter with suction, and recrystallize from acetonitrile to obtain the corresponding 6-bromo-1,3-dipolar quinazoline oxide, yellow solid, yield 67% . mp: 220-222℃; IR (KBr, υ / cm -1 ): 1931, 1816, 1733, 1601, 1498, 1366; 1 H NMR (400 MHz, DMSO): δ (ppm) 7.91(s, 2H), 8.19(s, 1H), 9.07(d, J = 2.0 Hz,1H), 9.18(d, J = 1....

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PUM

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of a novel 1,3-dipole quinazoline compound. The structure of the compound is represented and confirmed by using methods of 1HNMR, 13CNMR, IR, MS and the like. The novel 1,3-dipole quinazoline compound is prepared from a substituted benzaldoxime or a substituted benzylidene hydrazone compound and a triethyl orthoformate through cyclization reaction under the catalysis action of a lewis acid on mild conditions, wherein the substituted benzaldoxime or the substituted benzylidene hydrazone compound is prepared from a substituted benzaldehyde compound which has amino at the ortho-position. The preparation method for effectively preparing the 1,3-dipole quinazoline compound by using a serial method is mild in reaction condition, simple and convenient to operate, low in cost, less in side reaction, high in product purity, convenient to separate and purify, applicable to larger-scale preparation; and moreover the framework of the compound has broad biological activity and has good application prospect in pesticide and medicine research and development.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of a class of 1,3-dipole quinazoline compounds. Background technique [0002] In the past two decades, quinazoline pesticides and medicines have shown good biological activity and have become one of the research hotspots of scholars in the fields of chemistry and biology. Griess, P. first reported quinazolinone compounds (2-cyanoquinazolone compounds) in the 1869 and 1878 patents. In 1900, Bogert, M. T. also reported quinazoline derivatives, which aroused people's attention to this type of heterocyclic compounds. In 1915, people isolated the first indole quinazolinone alkaloid - Tryptanthrin 1 from a natural plant (Evodia rutaecarpa), and in 1998 Mitscher, L. A. found that it is a good antibacterial agent, especially against mycobacteria Very good antibacterial effect. In the 1950s, after the separation of Febrifugine 2 from Chinese h...

Claims

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Application Information

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IPC IPC(8): C07D239/76C07D239/74C07D491/056
Inventor 王涛罗金辉顾成浩李柔唐小丽于丹红李健
Owner JIANGXI NORMAL UNIV
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