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Synthetic method for (1,2,3-triazolyl)[1, 5-f]phenanthridine-10-ethyl carboxylate compound

A technology of ethyl carboxylate and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of difficult acquisition of raw materials, and achieve the effects of easy separation and purification, mild reaction conditions, and easy purchase

Inactive Publication Date: 2017-09-29
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because the raw materials are not easy to obtain, so far, there are no relevant literatures reporting the relevant synthetic methods of this type of compounds.

Method used

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  • Synthetic method for (1,2,3-triazolyl)[1, 5-f]phenanthridine-10-ethyl carboxylate compound
  • Synthetic method for (1,2,3-triazolyl)[1, 5-f]phenanthridine-10-ethyl carboxylate compound
  • Synthetic method for (1,2,3-triazolyl)[1, 5-f]phenanthridine-10-ethyl carboxylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]

[0018] Add 1a (1mmol, 102mg), ethyl 4-azidoacetoacetate 2 (1mmol, 171mg) and 2mL dioxane in a 10mL round bottom flask, then add cuprous iodide (0.1mmol, 19.1mg) and DMEDA (0.2mmol, 17.6mg), the resulting mixture was stirred at room temperature for 20min, then a mixed solution of 2mL acetonitrile and 3a (1mmol, 223mg) and sodium hydroxide (2.0mmol, 80mg) were added, and the temperature was raised to 80°C to continue the reaction for 2h, Then iodomethane (5mmol, 710mg) was added and reacted for another 1.5h. After the reaction was completed, 5 mL of water was added to quench the reaction, extracted with dichloromethane (5 mL×3), washed with saturated brine, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=8 / 1) to obtain the intermediate product 5-methyl-2-(4-phenyl-1H-1,2,3-triazolyl) -Ethyl 3-methoxy-2'-bromo-(1,1')-biphenyl-4-carboxylate (4aa, 196.8 mg, 40%). Then 4aa (0.5mmol, 246mg), pa...

Embodiment 2

[0022]

[0023]Add 1b (1mmol, 181mg), ethyl 4-azidoacetoacetate 2 (1mmol, 171mg) and 2mL dioxane in a 10mL round bottom flask, then add cuprous iodide (0.1mmol, 19.1mg) and DMEDA (0.2mmol, 17.6mg), the resulting mixture was stirred at room temperature for 20min, then a mixed solution of 2mL acetonitrile and 3a (1mmol, 223mg) and sodium hydroxide (2.0mmol, 80mg) were added, and the temperature was raised to 80°C to continue the reaction for 2h, Then iodomethane (5mmol, 710mg) was added and reacted for another 1.5h. After the reaction was completed, 5 mL of water was added to quench the reaction, extracted with dichloromethane (5 mL×3), washed with saturated brine, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain the intermediate product 5-methyl-2-(4-(4-bromophenyl)-1H-1,2,3- Triazolyl)-3-methoxy-2'-bromo-(1,1')-biphenyl-4-carboxylic acid ethyl ester (4ba, 307.8 mg, 54%). Then 4ba (0...

Embodiment 3

[0026]

[0027] Add 1c (1mmol, 116mg), ethyl 4-azidoacetoacetate 2 (1mmol, 171mg) and 2mL dioxane to a 10mL round bottom flask, then add cuprous iodide (0.1mmol, 19.1mg) and DMEDA (0.2mmol, 17.6mg), the resulting mixture was stirred at room temperature for 20min, then a mixed solution of 2mL acetonitrile and 3a (1mmol, 223mg) and sodium hydroxide (2.0mmol, 80mg) were added, and the temperature was raised to 80°C to continue the reaction for 2h, Then iodomethane (5mmol, 710mg) was added and reacted for another 1.5h. After the reaction was completed, 5 mL of water was added to quench the reaction, extracted with dichloromethane (5 mL×3), washed with saturated brine, and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=8 / 1) to obtain the intermediate product 5-methyl-2-(4-(4-methylphenyl)-1H-1,2,3 -Triazolyl)-3-methoxy-2'-bromo-(1,1')-biphenyl-4-carboxylic acid ethyl ester (4ca, 303.6 mg, 60%). Then 4ca ...

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Abstract

The invention discloses a synthetic method for a (1,2,3-triazolyl)[1, 5-f]phenanthridine-10-ethyl carboxylate compound, belonging to the technical field of organic synthesis. According to main points of a technical scheme in the invention, a reaction equation in the synthesis process of the method is as described in the specification. The method is mild in reaction conditions and simple in process; starting raw materials are noncyclic compounds like iodomethane, 4-azidoethyl acetoacetate, alkyne-terminated compounds and 1,2-allenyl ketones which are convenient to prepare or easy to purchase; the synthetic method can simultaneously construct three rings in a phenanthridine ring; and the finally synthesized compound is easy to separate and purify.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a synthesis method of (1,2,3-triazole)[1,5-f]phenanthridine-10-carboxylic acid ethyl ester compounds. Background technique [0002] Ethyl (1,2,3-triazole)[1,5-f]phenanthridine-10-carboxylates, as an important classical heterocyclic compound, are widely used in many fields such as medicine, materials and synthesis . However, because the raw materials are not easy to obtain, so far, there is no relevant literature reporting the relevant synthesis methods of this kind of compounds. Contents of the invention [0003] The technical problem solved by the present invention is to provide a synthetic method of (1,2,3-triazole)[1,5-f]phenanthridine-10-carboxylic acid ethyl ester compound, which has the starting The raw materials are simple and easy to prepare, the functional group compatibility is good, the reaction conditions are mild and the operation is simple a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 范云场王强邢万里赵霖宗朝在张帅
Owner HENAN POLYTECHNIC UNIV
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