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Alkynylated tetrahydroisoquinoline compound as well as preparation method and application thereof

A tetrahydroisoquinoline and compound technology, which is applied in the directions of organic chemistry, drug combination, pharmaceutical formulation, etc., can solve the problems of poor compatibility of alkyl alkynes, dangerous storage, complicated reaction operation, etc., and achieves novel structure and good biological activity. Effect

Inactive Publication Date: 2021-08-03
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are some disadvantages in this reaction. The compatibility of alkyl alkynes is poor. In addition, acetylene, propyne, and butyne are gases, which are dangerous to store and cumbersome to operate.

Method used

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  • Alkynylated tetrahydroisoquinoline compound as well as preparation method and application thereof
  • Alkynylated tetrahydroisoquinoline compound as well as preparation method and application thereof
  • Alkynylated tetrahydroisoquinoline compound as well as preparation method and application thereof

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Effect test

Embodiment 1

[0076] Embodiment 1 of the present invention is: a preparation method of alkynylated tetrahydroisoquinoline compounds, comprising the following steps:

[0077] In an undivided electrolyzer, add Cu(OTf) 2 (10mol%) and ligand L1 4,4'-tert-butylbipyridine (10mol%), n-Bu 4 NPF 6 (0.2mmol), tetrahydroisoquinoline 1a (0.2mmol), phenylpropylic acid 1b (0.24mmol), Et 3 N (0.24mmol), anhydrous MeCN (4mL), then insert platinum and nickel electrodes respectively as the anode and cathode of the reaction, electrolyze at a constant current of 1.5mA for 10h, after the reaction is completed, extract with ethyl acetate and collect the organic phase , and then the organic phases were mixed, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography to obtain compound 1 with a yield of 85%.

[0078] The characterization results of Compound 1 prepared in Example 1 of the present invention are ...

Embodiment 2

[0081] Embodiment 2 of the present invention is: a preparation method of alkynylated tetrahydroisoquinoline compounds, the difference from Embodiment 1 is that the ligand is replaced by L 2 4,4'-methoxybipyridine, the yield of compound 1 was 80%.

[0082]

Embodiment 3

[0083] Embodiment 3 of the present invention is: a preparation method of alkynylated tetrahydroisoquinoline compounds, the difference from Embodiment 1 is that the ligand is replaced by L 3 2,2'-methylbipyridine, the yield of compound 1 was 2%.

[0084]

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Abstract

The invention discloses an alkynylated tetrahydroisoquinoline compound and a preparation method and application thereof. The preparation method comprises the following steps that a tetrahydroisoquinoline compound shown in a formula (I) and an acetylenic acid compound shown in a formula (II) are added into an electrolysis system to serve as raw materials, and through an electrocatalytic decarboxylation reaction, the alkynylated tetrahydroisoquinoline compound as shown in a formula (III) is prepared. The decarboxylation coupling reaction of tetrahydroisoquinoline compounds (THIQs) and acetylenic acid is completed in one step.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to an alkynylated tetrahydroisoquinoline compound and its preparation method and application. Background technique [0002] Asymmetric catalysis has always been a hot research topic in organocatalytic reactions. The asymmetric cross-dehydrogenation coupling reaction (CDC) at the alpha position of cyclic amines has become one of the research hotspots, because its chiral products are easily derivatized into biologically active substances, especially tetrahydroisoquinoline derivatives (THIQs) cross-dehydrocouplings with relatively weak alkyne nucleophiles. In the related art, the asymmetric cross-dehydrogenation coupling reaction (CDC) of tetrahydroisoquinolines (THIQs) and terminal alkynes provides the C1 position with moderate enantioselectivity (5% to 74% ee). Alkylation product; also developed an aerobic oxidation method, but the reaction time is longer (24h ~ 72h), th...

Claims

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Application Information

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IPC IPC(8): C07D217/14C07D405/04C07C217/84A61P35/00A61K31/472A61K31/4725C07D455/03C25B3/05C25B3/07C25B3/09C25B3/11C25B3/29
CPCC07D217/14C07D405/04C07C217/84A61P35/00C07D455/03
Inventor 梅天胜高君青徐学涛杨祥
Owner WUYI UNIV
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