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Synthesis method of 9H-pyrido [3, 4-b] indole

A synthesis method, 4-b technology, applied in the direction of organic chemistry, etc., to achieve the effects of simple operation, low cost of raw materials, and mild reaction

Active Publication Date: 2021-11-02
SINOSTEEL ANHUI TIANYUAN TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The object of the present invention is to provide a synthetic method of 9H-pyrido[3,4-b]indole, which can solve the problem of pre-preparing and separating four in the existing 9H-pyrido[3,4-b]indole synthesis. Problems with Hydrogenated Carbolines

Method used

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  • Synthesis method of 9H-pyrido [3, 4-b] indole
  • Synthesis method of 9H-pyrido [3, 4-b] indole
  • Synthesis method of 9H-pyrido [3, 4-b] indole

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Embodiment 1

[0027] Embodiment 1: A kind of synthetic method of 9H-pyrido[3,4-b]indole

[0028] The preparation steps include: at room temperature under a nitrogen atmosphere, 20.4 g of tryptophan (Mr=204.23, 99.5%, 0.1 mol), 1.76 g of Fe(TPP)Cl (Mr=704.02, 99 %, 2.5mmol) and 27.64g of potassium carbonate (Mr=138.21, 99%, 0.2mol), then add 47.75g of chloroform (Mr=119.38, 99%, 0.4mol); feeding is complete, and the temperature is raised to 50°C , rotating speed 400rmp, carry out cycloaromatization reaction 8h, thin-layer chromatographic analysis (TLC) monitor; The crude product was recrystallized from isopropanol to obtain 5.81 g of 9H-pyrido[3,4-b]indole with a yield of 34.5%.

Embodiment 2

[0029] Embodiment 2: A kind of synthetic method of 9H-pyrido[3,4-b]indole

[0030] The preparation steps include: at room temperature under a nitrogen atmosphere, 20.4 g of tryptophan (Mr=204.23, 99.5%, 0.1 mol), 1.76 g of Fe(TPP)Cl (Mr=704.02, 99 %, 2.5mmol) and 27.64g of potassium carbonate (Mr=138.21, 99%, 0.2mol), then add 47.75g of chloroform (Mr=119.38, 99%, 0.4mol); feeding is complete, and the temperature is raised to 30°C , rotating speed 400rmp, carry out cycloaromatization reaction 12h, thin-layer chromatographic analysis (TLC) monitors; After the reaction finishes, filter insolubles and reclaim unreacted chloroform by distillation, add water and ethyl acetate to extract the residue, and remove the organic layer The crude product was recrystallized with isopropanol to obtain 5.00 g of 9H-pyrido[3,4-b]indole with a yield of 29.8%.

Embodiment 3

[0031] Embodiment 3: A kind of synthetic method of 9H-pyrido[3,4-b]indole

[0032] The preparation steps include: at room temperature under a nitrogen atmosphere, 20.4 g of tryptophan (Mr=204.23, 99.5%, 0.1 mol), 1.76 g of Fe(TPP)Cl (Mr=704.02, 99 %, 2.5mmol) and 27.64g of potassium carbonate (Mr=138.21, 99%, 0.2mol), then add 47.75g of chloroform (Mr=119.38, 99%, 0.4mol); feeding is complete, and the temperature is raised to 60°C , rotating speed 400rmp, carry out cycloaromatization reaction 10h, thin layer chromatographic analysis (TLC) monitor; The crude product was recrystallized with isopropanol to obtain 8.85 g of 9H-pyrido[3,4-b]indole with a yield of 52.7%.

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Abstract

The invention discloses a synthesis method of 9H-pyrido [3, 4-b] indole. The method comprises the following steps: taking tryptophan and chloroform as basic reaction raw materials, taking ferric salt as a catalyst, then adding alkali, carrying out cyclization aromatization reaction through free radical series connection, and finally carrying out post-treatment to obtain the 9H-pyrido [3, 4-b] indole product. According to the method, only commercially available tryptophan is used as a substrate, chloroform is used as a C1 source, a reaction precursor does not need to be prepared in advance, [5 + 1] cyclization aromatization is realized in a free radical series connection mode; and after C-C bond and C-N bond construction as well as decarboxylic acid and dehydrogenation aromatization process, without prior modification, addition of oxidizer, pre-preparation and separation of tetrahydrocarboline compounds, direct construction of pyridine heterocyclic slices can be realized througha one-pot method.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a synthesis method of 9H-pyrido[3,4-b]indole. Background technique [0002] 9H-pyrido[3,4-b]indole is an important class of nitrogen-containing heterocycles, which have a pyridine heterocycle slice structure, and are widely used in medicine, pesticides and materials. Hamarine, norhamarine, eudistomin U, I and N are representative β-kappa alkaloids containing such structures, which have potential medicinal value in antitumor, so for this kind of pyridine hetero The synthesis of ring slice structures has always been a research hotspot. In addition, although its structure is somewhat different from that of carbazole, its nitrogen content still increases its electron-rich property, so it has great application potential in electroluminescence. The existing synthesis of such compounds mainly contains the following methods: [0003] Method I: Patent (CN103864787A) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 吴忠凯朱叶峰杨修光张倩倩张玲裴晓东骆艳华申保金
Owner SINOSTEEL ANHUI TIANYUAN TECH
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