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Method for synthesis of indazolone compound

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve problems such as low yield, high requirements for reaction equipment, and many by-products, and achieve the effects of high reaction yield, high practical value, and easy operation

Inactive Publication Date: 2017-08-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The shortcomings of the above methods are that the use of transition metal catalysts brings heavy metal residues, requires ligands, many by-products, low yields, and high requirements for reaction equipment.

Method used

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  • Method for synthesis of indazolone compound
  • Method for synthesis of indazolone compound
  • Method for synthesis of indazolone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] In a 250mL round bottom flask, add potassium tert-butoxide (3.0g, 27.0mmol), 2-chloro-N'-phenylbenzohydrazide Ia (2.2g, 9.0mmol), tetrahydrofuran (135mL), and Reflux for 2 hours. After the reaction, THF was removed under reduced pressure, water (50 mL) was added, extracted with ethyl acetate (50 mL×3), the combined extracts were washed with saturated brine, and the solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate as eluent to obtain pure 1-phenylindazolone IIa (1.9 g, yield 99%). Melting point 165.0-166.9°C; 1 H NMR (400MHz, DMSO): δ11.24(s, 1H), 7.77(d, J=8.9Hz, 2H), 7.69(d, J=7.6Hz, 2H), 7.52(t, J=7.9Hz, 2H), 7.45(m, 1H), 7.26(t, J=7.4Hz, 1H), 7.16(t, J=7.7Hz, 1H); 13 C NMR (100MHz, DMSO): δ156.8, 140.7, 139.7, 123.0, 128.8, 125.2, 121.1, 121.0, 120.8, 115.3, 110.8; MS (ESI) C 13 h 11 N 2 O, [M+H] + : 211...

Embodiment 2

[0023] Using the same procedure as in Example 1, sodium tert-butoxide (2.6 g, 27.0 mmol) was used instead of potassium tert-butoxide to obtain 1-phenylindazolone IIa (0.61 g, yield 32%).

Embodiment 3

[0025] Using the same procedure as in Example 1, dimethylsulfoxide was used instead of N,N-dimethylformamide to obtain 1-phenylindazolone IIa (1.7 g, yield 92%).

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Abstract

The invention provides a novel method for synthesis of an indazolone compound. The method comprises that an alkali is added into o-halogenated aromatic formylhydrazine as a raw material, and the mixture is heated in a solvent so that a 1-aryl and 2-aryl indazolone compound having a high yield is obtained. The method is free of a transition metal catalyst, is simple in operation, has a high reaction yield and has a very high practical value in industrial preparation of the indazolone compound.

Description

technical field [0001] The invention relates to a method for synthesizing indazolone compounds, belonging to the field of organic synthesis. Background technique [0002] Indazolone compounds and their structural derivatives are widely used in the pharmaceutical industry. In recent years, there are more than 20 indazolone drugs that have been listed or are in the clinical research stage, and have many anti-cancer, anti-inflammatory, anti-HIV and anti-obesity properties. kind of activity. As early as 1800, Fisher synthesized indazolone compounds using o-hydrazinobenzoic acid. Since then, there have been many reports on the synthesis methods of indazolone compounds and structural derivatives thereof, mainly including the following types: (1) Copper-catalyzed intramolecular cyclization of o-halogenated aromatic hydrazides (Synlett, 2008 , 1973; Org.Biomol.Chem., 2012, 10, 1381; JP2009035531); (2) copper-catalyzed intermolecular reaction of N'-arylbenzohydrazide and 2-bromoace...

Claims

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Application Information

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IPC IPC(8): C07D231/56
CPCC07D231/56
Inventor 鄢明王卫娟张学景陈新滋
Owner SUN YAT SEN UNIV
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