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Preparation method of 2-amino fused pyridine compound

An amino-based fused pyridine and compound technology, which is applied in the field of preparation of 2-amino-based fused pyridine compounds, can solve the problems of difficulty in storage, poor stability of reaction substrates, narrow substrate selection range, etc., and achieves easy storage and performance. Superior, Inexpensive Effects

Active Publication Date: 2021-09-03
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Under such harsh reaction conditions, the reaction substrate has poor stability and is difficult to preserve. It is often synthesized from 2-substituted quinoline compounds, so the selection range of substrates is narrow

Method used

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  • Preparation method of 2-amino fused pyridine compound
  • Preparation method of 2-amino fused pyridine compound
  • Preparation method of 2-amino fused pyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017]

[0018] Take a 20mL reaction tube, add benzoxime ester compound 1a (0.6mmol), malononitrile-derived olefin compound 2a (0.2mmol), iron triacetylacetonate 0.01mmol, under the protection of inert gas (nitrogen or argon) , after addition of dioxane (2 mL), the reaction tube was sealed with a Teflon stopper. Place the reaction tube in a stirred oil bath at 110°C for 12 hours, and detect it by TLC. After the reaction is completed, cool down to room temperature, filter with diatomaceous earth, and then rinse with 20 mL of ethyl acetate for several times until the filtrate is colorless, and combine the organic phases , spin to remove the solvent to obtain a mixture containing 2-amino-6,6-dimethyl-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (3aa), and then flash column chromatography to obtain the product 3aa. Rate 90%.

[0019] 1 H NMR (600MHz, CDCl 3 )δ8.32(d,J=7.8Hz,1H),7.53-7.49(m,3H),7.43–7.41(m,1H),7.37–7.35(m,2H),7.31(d,J=6.9Hz ,2H),5.16(s,2H),2.53(s,2H)...

Embodiment 2

[0021]

[0022] Take a 20mL reaction tube, add benzoxime ester compound 1a (0.6mmol), malononitrile-derived olefin compound 2a (0.2mmol), ferrous acetylacetonate 0.01mmol, under the protection of inert gas (nitrogen or argon) , after addition of dioxane (2 mL), the reaction tube was sealed with a Teflon stopper. Place the reaction tube in a stirred oil bath at 110°C for 12 hours, and detect it by TLC. After the reaction is completed, cool down to room temperature, filter with diatomaceous earth, and then rinse with 20 mL of ethyl acetate for several times until the filtrate is colorless, and combine the organic phases , spin to remove the solvent to obtain a mixture containing 2-amino-6,6-dimethyl-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (3aa), and then flash column chromatography to obtain the product 3aa, harvested rate of 65%.

[0023] 1 H NMR (600MHz, CDCl 3 )δ8.32(d,J=7.8Hz,1H),7.53-7.49(m,3H),7.43–7.41(m,1H),7.37–7.35(m,2H),7.31(d,J=6.9Hz ,2H),5.16(s,2...

Embodiment 3

[0025]

[0026] Take a 20mL reaction tube, add benzoxime ester compound 1a (0.6mmol), malononitrile derivative olefin compound 2a (0.2mmol), ferric chloride 0.01mmol, under the protection of inert gas (nitrogen or argon), After addition of dioxane (2 mL), the reaction tube was sealed with a Teflon stopper. Place the reaction tube in a stirring oil bath at 110°C for 12 hours, and detect it by TLC. After the reaction is completed, cool down to room temperature, filter with diatomaceous earth, and then rinse with 20 mL of ethyl acetate for several times until the filtrate is colorless, and combine the organic phases , spin to remove the solvent to obtain a mixture containing 2-amino-6,6-dimethyl-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (3aa), and then flash column chromatography to obtain the product 3aa, harvested The rate is 79%.

[0027] 1 H NMR (600MHz, CDCl 3 )δ8.32(d,J=7.8Hz,1H),7.53-7.49(m,3H),7.43–7.41(m,1H),7.37–7.35(m,2H),7.31(d,J=6.9Hz ,2H),5.16(s,2H...

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Abstract

The invention relates to a synthesis method of a 2-amino fused pyridine compound, which is characterized in that a benzoyl oxime ester compound and a malononitrile derived olefin compound are used as raw materials to react in a reaction solvent under the protection of argon to obtain the 2-amino fused pyridine compound under the catalytic action of a cheap iron compound. The raw materials used in the method are simple and easy to obtain, are all industrial commodities, and are wide in source, low in price, stable in property and not harsh in preservation condition; secondly, the synthesis method is short in route, the 2-amido fused pyridine compound is constructed in one step by utilizing a multi-step free radical cascade reaction, the atom economy is high, the efficiency is excellent, the reaction yield is as high as 90%, the breakthrough progress of chemical synthesis of the system is realized, and the deep expansion of chemical research of related medicines of the system is promoted.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, in particular to a preparation method of a 2-amino-condensed pyridine compound. Background technique [0002] 2-Amino-fused pyridines are important intermediates in the synthesis of many natural products and drug molecules. At present, many anti-degenerative neurological disease drugs, receptor antagonists or agonists, and enzyme inhibitors are obtained by converting 2-amino-fused pyridine. Therefore, a series of methods for the synthesis of this class of compounds have been developed, however, these methods often require reaction at high temperature through expensive metal catalysts, multi-step synthesis, and need to be carried out under high temperature and pressure. Under this harsh reaction condition, the reaction substrate has poor stability and is difficult to preserve. It is often synthesized from 2-substituted quinoline compounds, so the selection range of substrates is narrow. ...

Claims

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Application Information

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IPC IPC(8): C07D221/10C07D405/04C07D417/04C07D409/04C07D471/04C07D221/20C07D491/113C07D221/18C07F17/02
CPCC07D221/10C07D405/04C07D417/04C07D409/04C07D471/04C07D221/20C07D491/113C07D221/18C07F17/02
Inventor 魏晔刘青鹏蒋坤
Owner SOUTHWEST UNIVERSITY
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