Simple synthesis method of 1-alkyl-3-aryl substituted indolizine compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of complex synthesis method, time-consuming and labor-intensive substrate synthesis, etc., and achieve the effects of simple synthesis process, simple operation, and easy availability of raw materials.

Active Publication Date: 2021-09-24
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these synthetic methods are relatively complex, a...

Method used

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  • Simple synthesis method of 1-alkyl-3-aryl substituted indolizine compound
  • Simple synthesis method of 1-alkyl-3-aryl substituted indolizine compound
  • Simple synthesis method of 1-alkyl-3-aryl substituted indolizine compound

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Embodiment 1

[0026]

[0027] Method 1: Into a 10mL reaction tube equipped with a reflux condensing device, add compound 1a and an aqueous inorganic acid solution, place in an oil bath to heat up and stir for reaction. After the reaction is completed, cool to room temperature, dilute with water, and then add potassium carbonate to neutralize the acidic aqueous solution until the reaction solution is alkaline and has a pH of 8-10. Ethyl acetate was extracted three times, the combined organic phases were dried, filtered and spin-dried, and separated on a silica gel column (petroleum ether) to obtain the green oily product 2a.

[0028] By changing reaction conditions such as inorganic acid concentration, solvent amount and reaction temperature of reaction, reaction result is as follows:

[0029] Synthesis of 2a under different conditions in table 1 a

[0030]

Embodiment 2

[0032]

[0033] Method 2: Add compound 1a, an organic acid catalyst, and an organic solvent into a 10mL reaction tube equipped with a reflux condensing device, mix thoroughly, and place in an oil bath to heat up and stir for reaction. After the reaction was completed, it was cooled to room temperature, spin-dried, and separated on a silica gel column (petroleum ether) to obtain the green oily product 2a.

[0034] By changing reaction conditions such as the organic acid catalyst of reaction and its consumption, organic solvent, solvent amount and reaction temperature, reaction result is as follows:

[0035] Synthesis of 2a under different conditions in table 2 a

[0036]

Embodiment 3

[0038]

[0039] Method 1: Add (E)-4-phenyl-2-pyridyl-3-enyl-2-ol (1a, 45.0mg, 0.2mmol) and 3.5M Aqueous hydrochloric acid solution (3 mL) was mixed thoroughly, and then stirred at 100° C. for 12 hours under an air atmosphere. After the reaction is completed, cool to room temperature, dilute with water, then add potassium carbonate to neutralize the acidic aqueous solution until the reaction solution is alkaline pH=8-10, extract three times with ethyl acetate, combine the organic phases to dry, filter with suction, spin dry, and pass through a silica gel column Isolation (petroleum ether) gave the product 2a (39.0 mg, 94%) as a green oil.

[0040] Method 2: Add (E)-4-phenyl-2-pyridyl-3-enyl-2-ol (1a, 45.0mg, 0.2mmol), p-toluene to a 10mL reaction tube equipped with a reflux condenser Sulfonic acid (3.8mg, 0.01mmol) and N,N-dimethylformamide (3mL) were thoroughly mixed and stirred at 100°C for 12 hours under air atmosphere. After the reaction was completed, it was cooled to...

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Abstract

The invention discloses a simple synthesis method of a 1-alkyl-3-aryl substituted indolizine compound, and belongs to the field of organic synthesis. According to the method, (E)-4-aryl-2-pyridyl-3-alkenyl-2-alcohol compounds 1 are used as raw materials and react under acid catalysis to obtain 1-alkyl-3-aryl substituted indolizine compounds 2, wherein the acid catalysis comprises two methods of catalysis in an inorganic acid aqueous solution and catalysis in an organic acid/organic solvent. The two methods provided by the invention are both completed through an acid catalytic dehydration intramolecular reaction, have different catalytic effects on substrates containing different substituent groups, and can complement each other's advantages; and meanwhile, the method has the advantages of simple and easily available raw materials, simple operation, wide substrate application range and the like.

Description

technical field [0001] The invention specifically relates to a synthesis method of 1-alkyl-3-aryl substituted indolizine compounds, belonging to the technical field of organic synthesis. Background technique [0002] Indolizine compounds and their derivatives, as important nitrogen-containing heterocycles, are common structures in natural product molecules and active pharmaceutical molecules. Central building blocks of sedative and anticancer drugs. Therefore, indolizine derivatives containing various substituent groups have important research significance as candidate drug molecules with potential drug activity. In addition, this type of compound is stable and has important applications in photochemistry. [0003] The multi-substituted indolizine compounds are mainly synthesized through intermolecular chemical reactions, and most of the existing methods are realized by metal complex catalysis, and the commonly used metals are rhodium, copper, cobalt, palladium, etc. In a...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 吕馨馨高鹏辉马源樊琳琳睢时辕江智勇
Owner HENAN NORMAL UNIV
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