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Method for synthesizing propargylamine derivative with different substituent groups at alkyne terminal

A technology of propargylamine and substituents, which is applied in the field of mutual conversion between different propargylamines, can solve the problems of unsuitable modification of end group of internal alkyne-type propargylamine, and achieves easy commercial purchase or preparation, high yield and moderate price Effect

Inactive Publication Date: 2016-04-13
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reaction between propargylamine and terminal alkyne has great limitations, and it is only suitable for the reaction between propargylamine without substituent at the other alkyne end, aryl acetylene and functional substituted acetylene, and the reaction yield is only 33-83%. Not suitable for end group modification of internal alkyne-type propargyl amines; also, the reaction is limited to tertiary amines

Method used

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  • Method for synthesizing propargylamine derivative with different substituent groups at alkyne terminal
  • Method for synthesizing propargylamine derivative with different substituent groups at alkyne terminal
  • Method for synthesizing propargylamine derivative with different substituent groups at alkyne terminal

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of N-benzyl-2-heptynylamine, structural formula is as follows:

[0031]

[0032] Under nitrogen protection, add raw material 1-hexyne (1.5mmol), N-benzyl-2-butynylamine (0.3mmol) and catalyst Lu[N(SiMe 3 ) 2 ] 3 (1mol%), xylene (2ml), reacted at 150°C for 48h, and the isolated yield of the product was 70%.

[0033] 1 HNMR (CDCl 3 ,400MHz,ppm):δ7.35-7.30(m,4H),7.27-7.25(m,1H),3.86(s,2H),3.40(t, J =2.12Hz,2H),2.23-2.19(m,2H),1.62(br,1H),1.52-1.40(m,4H),0.92(t, J =7.21Hz, 3H).

Embodiment 2

[0035] The preparation of N-benzyl-5-phenyl-2-pentynylamine, structural formula is as follows:

[0036]

[0037] Under nitrogen protection, add raw material phenylethylacetylene (1.5mmol), N-benzyl-2-butynylamine (0.3mmol) and catalyst Lu[N(SiMe 3 ) 2 ] 3 (10mol%), toluene (2ml), reacted at 130°C for 12h, and the isolated yield of the product was 95%.

[0038] 1 HNMR (CDCl 3 ,400MHz,ppm):δ7.31-7.20(m,10H),3.80(s,2H),3.38(t, J =2.14Hz,2H),2.83(t, J =7.51Hz, 2H), 2.52-2.49(m, 2H), 1.47(br, 1H).

Embodiment 3

[0040] The preparation of N-benzyl-4,4-dimethyl-2-pentynylamine, the structural formula is as follows:

[0041]

[0042] Under the protection of nitrogen, the raw material tert-butylacetylene (1.5mmol), N-benzyl-2-butynylamine (0.3mmol) and catalyst Sc[N(SiMe 3 ) 2 ] 3 (10mol%), toluene (2ml), reacted at 130°C for 12h, and the isolated yield of the product was 80%.

[0043] 1 HNMR (400MHz, CDCl 3 )δ7.34-7.32 (m, 4H), 7.27-7.24 (m, 1H), 3.86 (s, 2H), 3.39 (s, 2H), 1.65 (br, 1H), 1.24 (s, 9H).

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Abstract

The invention belongs to the technical field of organic synthesis and belongs to the method for synthesizing a propargylamine derivative with different substituent groups at the alkyne terminal. Mutual transformation of different propargylamine is realized through carbon-carbon single-bond activation, specifically, a compound terminal alkyne and propargyl substitute secondary amine to serve as raw materials under the catalysis system of rare earth, and the propargylamine derivative with various substituent groups at the alkyne terminal is prepared. According to the method, sources of raw materials are wide, the preparation is easy, the operation is simple and convenient, the selectivity is controllable, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for mutual transformation between different propargylamines realized by activating a carbon-carbon single bond. Background technique [0002] Propargylamine is an important class of organic compounds, not only an important structural unit of a large number of natural products and drug molecules, but also an important intermediate in organic synthesis. Therefore, the development of new methods that can meet different synthetic goals or modify propargylamines has always been an important topic in organic synthetic chemistry. [0003] In the existing technology for preparing propargylamine, the addition reaction of terminal alkynes and imines is mainly used to prepare propargylamine derivatives. The literature (Tetrahedron Lett, 2003, 44, 6767-6768 and Tetrahedron Lett, 2004, 45, 8281-8283) reported that alkynes and imines were used as raw materials, ...

Claims

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Application Information

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IPC IPC(8): C07C211/27C07C211/28C07C211/29C07C209/68C07F7/10
CPCC07C209/68C07F7/08C07C211/27C07C211/28C07C211/29
Inventor 周锡庚邵银林
Owner FUDAN UNIV
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