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Method for synthesizing N-phenyl indazole [3,2-b] quinazoline-7(5H)-ketone derivatives

A synthesis method and technology of phenylindazole, applied in the field of organic chemical synthesis, can solve problems such as complicated synthesis, and achieve the effects of high purity, reduced production cost and high product yield

Inactive Publication Date: 2014-08-20
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The disadvantage of this method is that the synthesis of the compound of formula (II) is relatively loaded down with trivial details, so there is still need and demand for improvement in simplicity and simplicity

Method used

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  • Method for synthesizing N-phenyl indazole [3,2-b] quinazoline-7(5H)-ketone derivatives
  • Method for synthesizing N-phenyl indazole [3,2-b] quinazoline-7(5H)-ketone derivatives
  • Method for synthesizing N-phenyl indazole [3,2-b] quinazoline-7(5H)-ketone derivatives

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0053] Preparation 1: N'-phenyl-2-amino-4-fluorobenzoic hydrazide

[0054] Add a stirring bar and 30 mL of organic solvent tetrahydrofuran into a clean flask, then add 40 mmol of isatoic anhydride compounds of the following formula (IV) and 48 mmol of phenylhydrazine compounds of the following formula (V), and heat to reflux for overnight reaction. After the reaction was completed, the organic solvent was removed by rotary evaporation, and the residue was added to absolute ethanol for recrystallization, suction filtration, and drying to obtain the compound of the following formula (II), with a yield of 89.5%. The reaction formula is as follows:

[0055]

[0056] Melting point: 214-215°C.

[0057] NMR: 1 HNMR (500Mz, CDCl 3 )δ7.65(m,1H),7.48(dd,J=6.0,8.5Hz,1H),7.28-7.24(m,2H),6.94-6.91(m,3H),7.42-6.36(m,2H) , 6.24 (d, J=3.0Hz, 1H), 5.72 (s, 2H).

preparation example 2

[0058] Preparation 2: N'-phenyl-2-amino-5-methoxybenzoic hydrazide

[0059] Add a stirring bar and 40mL of organic solvent tetrahydrofuran into a clean flask, then add 40mmol of isatoic anhydride compounds of the following formula (IV), and 60mmol of phenylhydrazine compounds of the following formula (V), and heat to reflux for overnight reaction. After the reaction, the organic solvent was removed by rotary evaporation, and the residue was added to absolute ethanol for recrystallization, suction filtration, and drying to obtain the compound of the following formula (II), with a yield of 91.7%. The reaction formula is as follows:

[0060]

[0061] Melting point: 209-210°C.

[0062] NMR: 1 HNMR (500Mz, DMSO-d 6 )δ10.10(s,1H),7.78(s,1H),7.24(d,J=3.0Hz,1H),7.17-7.14(m,2H),6.90-6.88(m,1H),6.80-6.78 (m,2H), 6.73-6.68(m,2H), 6.18(s,2H), 3.72(s,3H).

preparation example 3

[0063] Preparation Example 3: N'-p-trifluoromethylphenyl-2-aminobenzoic hydrazide

[0064] Add a stirring bar and 40 mL of organic solvent tetrahydrofuran into a clean flask, then add 40 mmol of isatoic anhydride compound of the following formula (IV), and 70 mmol of phenylhydrazine compounds of the following formula (V), and heat to reflux for overnight reaction. After the reaction was completed, the organic solvent was removed by rotary evaporation, and the residue was added to absolute ethanol for recrystallization, suction filtration, and drying to obtain the compound of the following formula (II), with a yield of 90.9%. The reaction formula is as follows:

[0065]

[0066] Melting point: 198-199°C.

[0067] NMR: 1 HNMR (500Mz, CDCl 3 )δ7.74(s,1H),7.51-7.49(m,3H),7.31-7.28(m,1H),6.99(d,J=8.5Hz,2H),6.73-6.70(m,2H),6.37 (d, J=3.0Hz, 1H), 5.55(s, 2H).

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Abstract

The invention relates to a method for synthesizing N-phenyl indazole [3,2-b] quinazoline-7(5H)-ketone derivatives. According to the synthesizing method, 2-aminobenzoyl hydrazide compounds are reacted with triethyl orthobenzoate compounds in organic solvents in the presence of catalysts and oxidants to obtain the N-phenyl indazole [3,2-b] quinazoline-7(5H)-ketone derivatives. Through specific combination and / or selection of the catalysts and the oxidants, relatively high product yield and purity are gained, and the reaction substrates are widened, so that the method has good application prospect and research value.

Description

technical field [0001] The present invention provides a synthetic method of quinazolinone derivatives, more specifically, provides a kind of N-phenylindazol[3,2-b]quinazolin-7(5H)-one derivatives The synthetic method of the present invention belongs to the field of organic chemical synthesis. Background technique [0002] As a new class of polycyclic nitrogen-containing heterocyclic compounds, quinazolinones can be used as structural building blocks of active drugs, pesticide compounds, etc., and play an important role in the field of organic chemistry. , chemical industry, etc. have broad application prospects. For example, many drugs such as the antihypertensive drug prazosin and the diuretic drug mebazolone belong to the class of quinazolinones. And in agricultural methods, it can be used as fungicide, herbicide, etc. For example, the high-efficiency acaricide Fenazaquin has been introduced to the market as an agricultural fungicide, and the modified quinazolinone hete...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 吴华悦杨渭光陈久喜刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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