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Preparation method of 3-alkyl indolizine derivative

A technology for indene derivatives and derivatives is applied in the field of organic synthetic chemistry, and can solve the problems of many steps, direct purchase, difficulty, etc., and achieve the effects of simple process flow, cheap and easy availability, and reduced production costs.

Active Publication Date: 2017-07-07
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are certain difficulties in the synthesis of 3-alkyl indolizine derivatives in the prior art. Not only the reaction process is long and there are many steps, but also expensive metals and ligands need to be used. In most cases, an anhydrous and oxygen-free environment needs to be satisfied. harsh reaction conditions, while raw material prices are high and most of them cannot be purchased directly from the market, thus resulting in high preparation costs

Method used

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  • Preparation method of 3-alkyl indolizine derivative
  • Preparation method of 3-alkyl indolizine derivative
  • Preparation method of 3-alkyl indolizine derivative

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0041] as attached figure 1 According to the technological process, 48 ​​microliters of pyridine (equivalent to 0.60 mmol) and 65 microliters of 1-bromobutane (equivalent to 0.60 mmol) were put into the reaction vessel, and 0.20 ml of N , N - Dimethylformamide, heated and stirred at 80 degrees for 2.0 hours, then added 19.2 mg of lithium hydroxide (equivalent to 0.80 mmol), 125.0 mg of TEMPO (equivalent to 0.80 mmol), N , N - Put 21 microliters of dimethylacrylamide (equivalent to 0.20 mmol) and 2.8 milliliters of dimethyl sulfoxide into a reaction vessel, heat and stir at 140 degrees Celsius for 24 hours until the reaction is complete, pour the reacted mixture into water, and filter , washed and isolated to obtain 32.7 mg of the target product of this example (71% yield).

[0042] The target product in Example 1 was analyzed by a nuclear magnetic resonance spectrometer (model: AVANCE 400MHz, manufacturer: Bruker, Switzerland) to obtain figure 2 The H NMR spectra shown an...

Embodiment 2

[0044] as attached figure 1 According to the technological process, 93.1 mg (equivalent to 0.60 mmol) of 4-phenylpyridine and 91.8 mg (equivalent to 0.60 mmol) of 1-bromo-3-methoxypropane are put into the reaction vessel together, without Add solvent 1, heat and stir at 90°C for 1.0 hour, then add 180 mg of cesium hydroxide (equivalent to 1.20 mmol), 156 mg of TEMPO (equivalent to 1.0 mmol), and 13 microliters of acrylonitrile (equivalent to 0.20 mmol) and 2.0 mL N , N - Put dimethylformamide into a reaction vessel, heat and stir at 150 degrees Celsius for 24 hours until the reaction is complete, pour the reacted mixture into water, filter, wash, and isolate 47.5 mg of the target product of this example (yield: 86 %).

Embodiment 3

[0046] as attached figure 1 According to the technological process, take 3,5-lutidine as 64.3 mg (equivalent to 0.60 mmol), 2-bromomethyl-1,3-dioxolane as 100 mg (equivalent to 0.60 mmol), and Put it into a reaction vessel, add 0.2 ml of 1,4-dioxane, heat and stir at 100 degrees for 3.0 hours, then add 80 mg of lithium tert-butoxide (equivalent to 1.00 mmol), 313 mg of TEMPO (equivalent to 2.0 mmol), dimethyl maleate 43.2 mg (equivalent to 0.30 mmol) and 3.0 ml N -Put methylpyrrolidone into a reaction vessel, heat and stir at 130 degrees Celsius for 36 hours until the reaction is complete, pour the reacted mixture into water, filter, wash, and isolate 72.0 mg of the target product of this example (yield: 72%) .

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Abstract

The invention discloses a preparation method of a 3-alkyl indolizine derivative. The method comprises the steps that N-alkyl pyridinium salt directedly prepared from a pyridine derivative and primary halogenated hydrocarbon is reacted with electron-poor alkene in the presence of alkali and 2,2,6,6-tetramethylpiperidinooxy (TEMPO), and the 3-alkyl indolizine derivative is prepared. The preparation method aims to develop the brand new preparation raw materials of the 3-alkyl indolizine derivative and the corresponding technology method so as to simply and easily synthesize the 3-alkyl indolizine derivative in an environmentally friendly mode at the low production cost under loose reaction conditions.

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 preparation method of 3-alkyl 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-hypertensive and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 胡华友刘燕王文慧何友亮曹丽支三军
Owner HUAIYIN TEACHERS COLLEGE
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