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2-(3-isoquinolinyl)-ethyl propionate derivative and synthesis method thereof

A technology based on ethyl propionate and isoquinoline, applied in the field of 2--ethyl propionate derivatives and its synthesis, can solve the problems of no reports, etc., and achieve the effects of simple operation, mild reaction conditions, and easy-to-obtain raw materials

Active Publication Date: 2020-04-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction of O-acetyl oxime with allenoic acid ester has not been reported yet.

Method used

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  • 2-(3-isoquinolinyl)-ethyl propionate derivative and synthesis method thereof
  • 2-(3-isoquinolinyl)-ethyl propionate derivative and synthesis method thereof
  • 2-(3-isoquinolinyl)-ethyl propionate derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] The specific process is: weigh O-acetyl oxime 2a (53mg, 0.3mmol) in the glove box, [RhCp*Cl 2 ] 2 (3.7mg, 0.006mmol), pivalic acid (6.1mg, 0.06mmol), was added to a 25mL tube with a branch port, and ethyl allenoate 3a (76mg, 0.6mmol) was added under nitrogen atmosphere, 1, 2-Dichloroethane (3 mL) was reacted at 60° C. for 24 h. After the reaction was complete, the solvent was removed by rotary evaporation under reduced pressure, and then silica gel column chromatography (petroleum ether (60-90° C.) / ethyl acetate: 20:1, v / v) was used to obtain a colorless liquid product 1a (62 mg, harvested rate 85%). The target product was confirmed by NMR spectroscopy.

Embodiment 2

[0031]

[0032] The reaction steps and operations are the same as in Example 1, except that the O-acetyl oxime added to the reaction system is 2b (57 mg, 0.3 mmol). The reaction was stopped, and the target product 1b (68 mg, yield 88%) was obtained as a light yellow liquid after post-processing. The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0034]

[0035] The reaction steps and operations are the same as in Example 1, except that the O-acetyl oxime added to the reaction system is 2c (62 mg, 0.3 mmol). The reaction was stopped, and the target product 1c (75 mg, yield 92%) was obtained as a light yellow liquid after post-processing. The target product was confirmed by NMR and high-resolution mass spectrometry.

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PUM

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Abstract

The invention discloses a 2-(3-isoquinolinyl)-ethyl propionate derivative and a synthesis method thereof. According to the invention, O-acetyloxime with characteristics of easy preparation, structuraldiversity and multiple reaction centers is used as a raw material, the ortho-position C-H bond of the aromatic ring in the O-acetyloxime is activated under the action of a rhodium salt, a coupling reaction with allenoate is carried out, a series of 2-(3-isoquinolinyl)-ethyl propionate derivatives with different structures are synthesized, and the product can be further converted into a functionalproduct.; and the method has the advantages of easily available raw materials, simple operation, mild reaction conditions, diverse functional groups, and no need of pre-functionalization.

Description

technical field [0001] The invention relates to a 2-(3-isoquinolyl)-propionic acid ethyl ester derivative and a synthesis method thereof. Using O-acetyl oxime, which is easy to prepare, has structural diversity and multiple reaction centers, as a raw material, under the action of rhodium salt, the ortho-position C-H bond of the aromatic ring in O-acetyl oxime is activated to couple with allenoate A series of 2-(3-isoquinolinyl)-propionic acid ethyl ester derivatives with different structures were synthesized. Compared with the existing synthetic method of isoquinoline derivatives, the raw materials of the present invention are easy to obtain, easy to operate, mild in reaction conditions, and environmentally friendly; and do not need to add any oxidizing agent or reducing agent in the reaction, without pre-functionalization, and have atomic economical features. Background technique [0002] Compared with traditional methods, carbon-hydrogen bond activation and functionaliza...

Claims

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Application Information

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IPC IPC(8): C07D217/14C07D217/02C07D217/16
CPCC07D217/14C07D217/02C07D217/16
Inventor 余正坤汪全南
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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