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Green preparation method for 3-alkenyl indolizine derivative

An indene derivative and alkenyl technology is applied in the field of organic synthetic chemistry, and can solve the problems of rising raw material cost, environmental hazards, complicated process flow, etc., and achieve the effects of reducing synthesis cost, simple process flow, and cost reduction.

Inactive Publication Date: 2016-02-24
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some technologies require the addition of other metal catalysts and expensive ligands
There are following deficiencies in the prior art: one is that excessive alkali needs to be added, which directly leads to the rise of raw material costs and the complexity of the process (removing excess alkali from the reaction mixture) and the increase of waste water and waste residue; the other is that the existing Excessive transition metal salts must be used as oxidants in the process, which significantly increases synthesis costs and environmental protection expenses; third, when there are omissions in the operation of the process, a large amount of transition metal salts will be harmful to the environment

Method used

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  • Green preparation method for 3-alkenyl indolizine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] as attached figure 1 process flow, take 1- N , N -Dimethylcarbamido-indolizine is 38.0 mg (equivalent to 0.20 mmol), butyl acrylate is 57 microliters (equivalent to 0.40 mmol), palladium acetate is 2.2 mg (equivalent to 0.010 mmol), acetic acid 10.0 mg of potassium (equivalent to 0.10 mmol) and 2.0 ml of dimethyl sulfoxide were heated and stirred at 100 degrees Celsius for 5 hours under 1 atmospheric pressure of oxygen, and 56.0 mg of the target product 3-alkenyl indolizine derivative of Example 1 was isolated (The yield is 89%).

[0037] The target product in Example 1 was analyzed by nuclear magnetic resonance spectrometer (model: AVANCE400MHz, manufacturer: Bruker, Switzerland) to obtain figure 2 The H NMR spectra shown and image 3 The carbon NMR spectrum shown. The parameters of the former are 1 HNMR (CDCl 3 ,400MHz):8.22(d, J =7.0Hz,1H),7.94(d, J =8.2Hz,1H),7.91(d, J =15.4Hz,1H),7.31(s,1H),7.04(dd, J =8.6,6.9Hz,1H),6.82(t, J =6.6Hz,1H),6.28(d, J =15....

Embodiment 2

[0039] as attached figure 1 The technical process, take 1,2-dicarbonate ethyl-indolizine as 52.2 mg (equivalent to 0.20 mmol), N , N- 51.6 µl (equivalent to 0.50 mmol) of dimethylacrylamide, 1.1 mg (equivalent to 0.0050 mmol) of palladium acetate, 12.0 mg (equivalent to 0.12 mmole) of potassium acetate, 2.0 mL of dimethylsulfoxide Under 1 atmospheric pressure of oxygen, heating and stirring at 100°C for 6 hours, 68.1 mg of the target product of Example 2 was isolated (95% yield).

Embodiment 3

[0041] as attached figure 1 The technological process of taking 2,5-dimethyl-1-cyano-indolizine is 34.0 mg (equivalent to 0.20 mmol), dimethyl maleate is 28.8 mg (equivalent to 0.20 mmol), acetic acid 4.5 mg of palladium (corresponding to 0.02 mmol), 13.5 mg of sodium bicarbonate (corresponding to 0.16 mmol) and 2.0 ml of N,N-dimethylformamide were heated and stirred at 110 degrees Celsius for 16 hours under 1 atmosphere of oxygen, 40.0 mg of the target product of Example 3 was isolated (64% yield).

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Abstract

The present invention discloses a green preparation method for a 3-alkenyl indolizine derivative. The method comprises the following steps: starting from indolizine substituted by 3-bit hydrogen; under the condition that a catalytic amount of a palladium catalyst and alkali exists or the alkali is not added, using oxygen from the air as a unique oxidant to react with electron deficient olefin; and preparing to obtain the 3-alkenyl indolizine derivative. The present invention aims to synthesize the 3-alkenyl indolizine derivative in a simple and environmental friendly way by a low production cost under a loose reaction condition by developing the oxidant that can be used in preparation of the 3-alkenyl indolizine derivative and a corresponding process.

Description

technical field [0001] The invention relates to organic synthesis chemistry technology, in particular to a preparation method of indolizine derivatives, in particular to a green preparation method of 3-alkenyl indolizine derivatives. Background technique [0002] Indolizine derivatives are widely used in the fields of biology, pesticides, medicine and luminescent materials, and are necessary for the production of drugs, dyes and organic luminescent materials. For example: it is an active ingredient in pigments, herbicides, latent phospholipase inhibitors, anti-Leishmania and antiviral drugs; in addition, it also exhibits anti-mycobacterial activity; it is a synthetic compound with important physiological activities Key intermediates of alkaloids. In recent years, studies have confirmed that the biological activity of indolizine derivatives has also played a positive role in anti-tumor, anti-bacterial, anti-virus, acaricidal, anti-inflammatory, anti-arrhythmic, anti-hyperten...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 胡华友吉民顾宁
Owner SOUTHEAST UNIV
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