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3-aryl indolizine acetate derivative and preparation method and application thereof

A technology for aryl indolezine acetates and derivatives, which is applied in the field of 3-aryl indolezine acetate derivatives and its preparation, can solve the problems of difficult aryl chloride bonds and poor chemical reactivity, and achieve The reaction conditions are mild, the reaction effect is good, and the reaction reagent is stable and easy to obtain.

Inactive Publication Date: 2016-07-13
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Under palladium-catalyzed conditions, the use of aryl chlorides as substrates is relatively more challenging due to their poor chemical reactivity and the difficulty of oxidizing aryl chloride bonds with palladium.

Method used

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  • 3-aryl indolizine acetate derivative and preparation method and application thereof
  • 3-aryl indolizine acetate derivative and preparation method and application thereof
  • 3-aryl indolizine acetate derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0039](1) Preparation of indolezine: first slowly add bromoacetic acid (50mmol) to a solution of pyridine (50mmol) in ethyl acetate (30mL), stir the mixture at room temperature for 3 hours, filter and dry to obtain white solid N-(carboxymethyl base) pyridinium bromide. N-(carboxymethyl)bromopyridinium salt (10mmol, 2.04g), vinyl acetate (30mmol), triethylamine (1.5mL), active manganese dioxide (80mmol) were reacted in toluene (80mL) at 90°C for 2 hours , TLC detects the reaction, after the reaction is completed, the solid is filtered off and washed with acetone, the combined organic phase is spin-dried, and the mixture is separated by column to obtain indolezine acetate.

[0040] (2) Indoleazine arylation reaction: Indoleazine acetate (0.3mmol), sodium aryl sulfinate (0.6mmol), catalyst (0.03mmol), ligand (0.05mmol), oxidant (0.3mmol) Mix in acetonitrile (2mL), react at 100°C for 6h under nitrogen protection, after TLC detects that the reaction is complete, cool to room tempe...

Embodiment 1～20

[0043] The catalysts of Examples 1-20 were palladium acetate, without adding ligands, and reacted with different oxidants. The reaction results are shown in Table 1.

[0044] The reaction conditions and the result of table 1 embodiment 1~20

[0045] Example

Embodiment 21～37

[0047] The oxidant of Examples 21-37 was tert-butyl peroxyacetate, and the catalyst and ligand were changed. The results obtained are shown in Table 2.

[0048] The reaction conditions and the result of table 2 embodiment 21~37

[0049] Example

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Abstract

The invention discloses a 3-aryl indolizine acetate derivative and a preparation method and application thereof. The preparation method comprises the following steps of under the actions of a bivalent palladium catalyst, a nitrogen-containing ligand and peroxide, enabling indolizine acetate and aryl sulfinic acid sodium salt to generate desulfurization arylation reaction; after the reaction is completed, performing post-treatment, so as to obtain the 3-aryl indolizine acetate derivative. The preparation method has the advantages that by adding the particular peroxide additive into the reaction system, the reaction is effectively promoted, the self coupling reaction of the aryl sulfohydrazideis inhibited, and the reaction yield is improved; the reaction reagents are stable and can be easily obtained, so that the large-batch production is conveniently realized, and a new effective path is provided for building the structure; after proofing by the activity test results, the product can certainly inhibit the cell proliferation, and the certain anti-tumor activity is realized; the preparation method and the product have the important application meaning in the field of medicines.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a 3-aryl indolezine acetate derivative and a preparation method and application thereof. Background technique [0002] Today, indoxazines have become an important class of nitrogen-containing heterocyclic structures, which are commonly found in the fields of natural product synthesis and medicine. Indolezines derivatives exhibit antibacterial activity, estrogen receptor binding activity, antituberculous activity, phosphatase inhibitory activity and anticancer activity. and have been obtained as antidiabetic, anti-inflammatory, antihistamine and antiacetylcholine agents, antioxidants, phosphodiesterase inhibitors, PDE5A inhibitors, L-type calcium channel blockers and synthesis inhibitors of leukotrienes It has been widely used (V. Sharma and V. Kumar, Med. Chem. Res. 2014, 23, 3593.). [0003] Therefore, a number of methods for the synthesis of functionalized indoleaz...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P35/00
CPCC07D471/04
Inventor 朱余玲赵保丽
Owner SHAOXING UNIVERSITY
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