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Indolizine derivative and preparation method thereof

A derivative, indolazine technology, applied in the field of indolizine derivatives and their preparation, can solve the problems of complex catalyst preparation, unreusable, difficult product separation, etc., and achieves no catalyst residue, reduced burden, and atom economy. high effect

Pending Publication Date: 2020-11-10
苏州新森智能科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing indolezine derivatives have complex synthesis operations, harsh reaction conditions, expensive raw materials, rely on transition metal catalysts, complex catalyst preparation, cannot be reused, are relatively expensive, and difficult to separate products, and there are problems such as metal residues.

Method used

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  • Indolizine derivative and preparation method thereof
  • Indolizine derivative and preparation method thereof
  • Indolizine derivative and preparation method thereof

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preparation example Construction

[0037] A kind of preparation method of the indoxazine derivative of formula (I) structure, comprises the following steps:

[0038] Under nitrogen atmosphere, mix the compound 1 with the structure of formula (II), the compound 2 with the structure of formula (III), the catalyst and the accelerator in the reaction solvent, and carry out the [3+2] cycloaddition reaction under stirring , to obtain indolezine derivatives;

[0039]

[0040] In formula (II), R 1 Be any in phenyl, substituted phenyl, substituted heteroaryl; In formula (III), R 2 is phenyl, substituted phenyl, hydrogen, benzyl, C 1 -C 20 Any of the alkyl groups; R 3 is an alkyl or aryl group.

[0041] The reaction formula of [3+2] cycloaddition reaction is as follows:

[0042]

[0043] Wherein, the molar ratio of compound 1 and compound 2 is 1:(1-3).

[0044] The above-mentioned catalyst is an inorganic base, and the accelerator is a Lewis base.

[0045] Wherein, the inorganic base is at least one of pota...

Embodiment 1

[0061] A kind of indoxazine derivative, the structure is Prepared by:

[0062] 1) Preparation of 1-(2-oxo-2-arylethyl)pyridinium bromide

[0063] Pyridine (2.0 times the amount of a-bromoacetophenone) and a-bromoacetophenone were stirred in ether solution for 2 hours, a large amount of solid precipitated, then filtered, washed with ether, and dried to obtain white pyridinium bromide salt. The reaction formula is as follows:

[0064]

[0065] 2) Preparation of butadienoate

[0066] Dissolve 10mmol of alkoxyacylmethyl triphenylphosphine bromide in 50ml of dichloromethane, then add 22mmol of triethylamine, after 1 hour of reaction, slowly add 11mmol of acid chloride dropwise into the mixed system, and wait for 24 After 1 hour, the solvent was removed, extracted with ether, spin-dried, and separated by column chromatography (ethyl acetate:petroleum ether=1:40) to obtain the obtained product. The specific reaction is as follows:

[0067]

[0068] 3) Preparation of Indox...

Embodiment 2

[0073] A kind of indoxazine derivative, structure is identical with embodiment 1, is prepared by the following method:

[0074] 1) Preparation of 1-(2-oxo-2-arylethyl)pyridinium bromide

[0075] Pyridine (1.0 times the amount of a-bromoacetophenone) and a-bromoacetophenone were stirred in ether solution for 2 hours, a large amount of solid precipitated, then filtered, washed with ether, and dried to obtain white pyridinium bromide salt.

[0076] 2) Preparation of butadienoate

[0077] Dissolve 10mmol of alkoxyacylmethyl triphenylphosphine bromide in 50ml of dichloromethane, then add 20mmol of triethylamine, after 1 hour of reaction, slowly add 10mmol of acid chloride dropwise to the mixed system, and wait for 24 After 1 hour, the solvent was removed, extracted with ether, spin-dried, and separated by column chromatography (ethyl acetate:petroleum ether=1:40) to obtain the obtained product.

[0078] 3) Preparation of Indoxazine Derivatives

[0079] Under a nitrogen atmospher...

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Abstract

The invention discloses an indolizine derivative and a preparation method thereof. The indolizine derivative is prepared from pyridinium bromide and allenic acid ester through [3+2] cycloaddition reaction in a reaction solvent under the action of an inorganic base catalyst and a Lewis base promoter in a nitrogen atmosphere. The reaction substrate of the preparation method is simple, easy to synthesize and low in price; wherein the [3+2] cycloaddition reaction has the advantages of mild reaction conditions, high reaction efficiency, high indolizine derivative yield and high atom economy. Therefore, the indolizine derivative has the advantages of no catalyst residue, high purity and high application value.

Description

technical field [0001] The invention relates to the technical field of organic compound preparation, in particular to an indolezine derivative and a preparation method thereof. Background technique [0002] Indolezine derivatives are an important class of nitrogen-containing heterocyclic compounds, molecules with biological and pharmaceutical activities, and also a wide range of organic synthesis intermediates; indolezine structural units are widely found in natural products with biological activity And synthetic drugs, has broad application prospects. [0003] At present, there are relatively few studies on the synthesis and application of indolezine derivatives. Although there have been some reports on the synthesis of indolezine functionalization methods, no pyridinium bromide salts and allenoate [3+2] cycloaddition methods have been reported. A method for the preparation of indoxazine derivatives by synthetic reaction appeared. The existing indolezine derivatives have ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 王昌陆世锋陈才
Owner 苏州新森智能科技有限公司
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