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2-(3-amino-2-oxoindolin-3-yl)-3-hydroxyl-1,4-naphthoquinone derivative and preparation method thereof

A technology for indole alkanes and derivatives is applied in the field of 2--3-hydroxy-1,4-naphthoquinone derivatives and their preparation, and achieves the effects of high yield, mild reaction conditions and convenient post-processing

Active Publication Date: 2014-09-10
乐陵市博奥泡沫制品有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] 2-(3-Amino-2-oxoindolane-3-yl)-3-hydroxy-1,4-naphthoquinone derivatives, all of which contain 3-amino-2-oxoindole and 1, The structure of 4-naphthoquinone is a new class of compounds with important application value and biological activity, but there is no relevant report yet

Method used

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  • 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxyl-1,4-naphthoquinone derivative and preparation method thereof
  • 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxyl-1,4-naphthoquinone derivative and preparation method thereof
  • 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxyl-1,4-naphthoquinone derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: (IV-1) Preparation of 2-(3-amino-2-oxoindoalkyl-3-yl)-3-hydroxyl-1,4-naphthoquinone

[0025] Add isatin (147mg, 1mmol), 2-hydroxy-1,4-naphthoquinone (174 mg, 1mmol), ammonium acetate (116 mg, 1.5mmol) into ethanol (5ml), heat to reflux, track by TLC, 2h After the reaction is over, cool, filter with suction, wash, and dry to obtain the orange solid product (IV-1) 2-(3-amino-2-oxoindolane-3-yl)-3-hydroxyl-1,4- Naphthoquinone (314 mg, 98%), m.p. 266-268°C.

[0026] 1 H NMR (500 MHz, DMSO– d 6 ) δ 10.64 (s, 1H), 9.30 (s, 3H), 7.83 (d, J = 7.5 Hz, 2H), 7.71 (t, J = 7.1 Hz, 1H), 7.59 (td, J = 7.5, 1.2 Hz, 1H), 7.42 (d, J = 7.4 Hz, 1H), 7.25 (td, J = 7.7, 1.1 Hz, 1H), 6.91 (t, J = 7.6 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H); 13 C NMR (126 MHz, DMSO– d 6 ) δ 184.0, 174.6, 142.7, 133.9, 131.0, 130.9, 129.8, 129.1, 125.4, 125.1, 124.6, 121.7, 109.6, 61.3;

[0027] ESI-MS (m / z): 321.0 [M+H] + .

[0028] Among the above-mentioned examples, the source of ...

Embodiment 2

[0029] Example 2: (IV-1) Preparation of 2-(3-amino-2-oxoindolane-3-yl)-3-hydroxyl-1,4-naphthoquinone

[0030] The same operation as in Example 1, adding glacial acetic acid (0.01ml, 0.2mmol), and refluxing for 2 h, the orange solid product (IV-1) 2-(3-amino-2-oxoindolane-3- yl)-3-hydroxy-1,4-naphthoquinone (299 mg, 93%).

Embodiment 3

[0031] Example 3: (Ⅳ-1) Preparation of 2-(3-amino-2-oxoindolane-3-yl)-3-hydroxyl-1,4-naphthoquinone

[0032] With the operation of Example 1, cesium carbonate (65 mg, 0.2 mmol) was added, and after reflux for 2 h, the orange solid product (IV-1) 2-(3-amino-2-oxoindolane-3-yl )-3-Hydroxy-1,4-naphthoquinone (250 mg, 78%).

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Abstract

The invention provides a 2-(3-amino-2-oxoindolin-3-yl)-3-hydroxyl-1,4-naphthoquinone derivative and a preparation method thereof, and belongs to the technical field of compound synthesis. The preparation method comprises the following steps: dissolving isatin derivative as shown in the formula (I), 2-hydroxyl-1,4-naphthoquinone as shown in the formula (II) and an ammonia source as shown in the formula (III) in a solvent; sufficiently stirring to react under a reflux state; tracking by TLC (thin layer chromatography) until the raw materials are completely reacted; cooling, performing suction filtering, and baking to obtain the target product. The preparation method has the advantages of mild reacting condition, simple operation, convenience in post-treatment and high yield which is over 98 percent at most and the melting range of the prepared product is short; the structures of corresponding compounds are certified by IR (infrared radiation), 1HNMR (1H nuclear magnetic resonance), 12CNMR (12C nuclear magnetic resonance) and ESI-MS (electrospray ionization mass spectrometry), and monocrystal can be cultured by a part of target products.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and specifically relates to a 2-(3-amino-2-oxoindolane-3-yl)-3-hydroxyl-1,4-naphthoquinone derivative and a preparation method thereof. Background technique [0002] Multicomponent reactions refer to the process of three or more compounds forming a new compound containing the main structural fragments of all components in a one-pot reaction (Multicomponent Reactions, MCRs). Compared with traditional reactions, multicomponent reactions are more in line with the principle of atom economy, and are easy to operate and relatively convenient in post-processing, which has great advantages in generating the complexity and diversity of molecular structures. Therefore, multicomponent reactions have a wide range of applications in the design and synthesis of new drugs, combinatorial chemistry and natural product synthesis. [0003] The 3-amino-2-oxoindole structure exists in many biologically ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/40C30B29/54
CPCC07D209/40C30B29/54
Inventor 宋庆宝车峰峰张诚沈田华
Owner 乐陵市博奥泡沫制品有限公司
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