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A synthetic method of 3-seleno indoles

A technology of selenoindole and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of dependence, narrow substrate range, low universality, etc., and achieves the effects of simple and mild reaction conditions, easy operation, and cheap and easily available raw materials

Active Publication Date: 2018-03-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In these synthetic methods, there are often limitations such as the need for high-temperature reactions, reliance on transition metal catalysis, narrow substrate scope, and low universality.

Method used

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  • A synthetic method of 3-seleno indoles
  • A synthetic method of 3-seleno indoles
  • A synthetic method of 3-seleno indoles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of 1H-indol-3-yl-(Z)-N,N-diethyl-N'-(3-nitrophenyl)carbaimide selenate

[0039] Weigh 0.3mmol3-nitrophenyl isonitrile (compound corresponding to numbering (1), 0.0444g), 0.36mmol Se (0.0284 g), 0.36mmol indole (compound corresponding to numbering (14), 0.0422g), 0.36 Add mmol diethylamine (compound corresponding to number (28), 0.0263g, 38μL), 0.6mmol cesium carbonate (0.2117g) in a 20mL test tube reaction tube, add 2mL tetrahydrofuran as solvent, and stir at 40°C for 12 hours; After the reaction, the reaction solution was spin-dried, loaded and separated by column chromatography (column chromatography separation conditions: the stationary phase was 300-400 mesh silica gel powder, and the mobile phase was ethyl acetate (A) and petroleum ether (B). , the mobile phase change program (A:B) is 1:8), and 0.0810 g of the reaction product was obtained.

[0040] The above-mentioned reaction product is characterized, and the result is:

[0041] 1 H NMR (400MHz, CDCl...

Embodiment 2

[0044] Synthesis of 1H-indol-3-yl-(Z)-N,N-diethyl-N'-(3-nitrophenyl)carbaimide selenate

[0045] Weigh 0.3mmol3-nitrophenyl isonitrile (compound corresponding to numbering (1), 0.0444g), 0.36mmol Se (0.0284 g), 0.36mmol indole (compound corresponding to numbering (14), 0.0422g), 0.36 mmol diethylamine (number (28) corresponding compound, 0.0263g, 38μL), 0.6mmol cesium carbonate (0.2117g) and 0.06mmol2,2,6,6-tetramethylpiperidine oxide (0.0094g) in In a 20mL test tube reaction tube, add 2mL tetrahydrofuran as a solvent, and stir and react at 40°C for 16 hours; ~400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:8), and 0.1171g of the reaction product is obtained.

[0046] The above-mentioned reaction product is characterized, and the result is:

[0047] 1 H NMR (400MHz, CDCl 3) δ = 8.32 (s, 1H), 7.40–7.31 (m, 2H), 7.20–7.07 (m, 4H), 6.87 (t, J = 8.0Hz, 1H), 6.63 (dd ,J=7.8,1.2Hz,1H),6.58(d,J=...

Embodiment 3

[0050] Synthesis of 1H-indol-3-yl-(Z)-N,N-diethyl-N'-(4-nitrophenyl)carbaimide selenate

[0051] Weigh 0.3mmol 4-nitrophenyl isonitrile (compound corresponding to numbering (2), 0.0444g), 0.36mmol Se (0.0284 g), 0.36mmol indole (compound corresponding to numbering (14), 0.0422g), 0.36 mmol diethylamine (number (28) corresponding compound, 0.0263g, 38μL), 0.6mmol cesium carbonate (0.2117g) and 0.06mmol2,2,6,6-tetramethylpiperidine oxide (0.0094g) in In a 20mL test tube reaction tube, add 2mL tetrahydrofuran as a solvent, and stir and react at 40°C for 16 hours; ~400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B) is 1:8), and 0.0679g of the reaction product is obtained.

[0052] The above-mentioned reaction product is characterized, and the results are as follows:

[0053] 1 H NMR (400MHz, DMSO-d 6 )δ=11.29(s,1H),7.68–7.62(m,2H),7.27(dd,J=18.9,7.6 Hz,2H),7.09–7.01(m,2H),6.86(d,J=2.7Hz ,1H),6.33–6....

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Abstract

The invention relates to a synthetic method of 3-seleno indoles. An isonitrile compound shown as a formula (I), elemental selenium shown as a formula (II), an indole compound shown as a formula (III)and a secondary amine shown as a formula (IV) are reacted at 25-70 DEG C under functions of an alkali in an air atmosphere by adopting an organic solvent as a reaction medium to obtain one of the 3-seleno indoles shown as a formula (V). The reaction route is shown in the specification, wherein R1 is selected from nitro, cyano, acetyl, acylamino, alkyl, alkoxy, an ester group, trifluoromethyl or halogen, R2 is selected from hydrogen, phenyl, substituted phenyl or alkyl, and R3, R4 and R5 are independently selected from hydrogen, phenyl, alkyl, cyano, nitro, an ester group, alkoxy or halogen. The secondary amine shown as the formula (IV) is selected from noncyclic aliphatic secondary amines, cyclic aliphatic secondary amines or aromatic secondary amines. Reaction conditions of the method aremild and the method is environmentally-friendly.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing 3-selenoindole compounds. Background technique [0002] Selenium-containing skeletons widely exist in drug precursors, bioactive compounds, and other organic materials, and have potential application value and broad application prospects in the fields of medicine and pharmacy. For example: Ebselen has shown strong anti-inflammatory properties. Studies have shown that 3-thioindole derivatives have good therapeutic effects on AIDS, cancer, heart disease and allergies, and can also be used as inhibitors of tubulin polymerization (Nat.Rev.Drug Discovery, 2005, 4, 664; J Med. Chem., 2007, 50, 2865; J. Med. Chem., 2006, 49, 3172; J. Med. Chem., 2006, 49, 947). As a congener element of sulfur, selenium has many similarities with sulfur in chemical properties, and has stronger reducibility. Therefore, it is of great significance to study the synthesis of 3-se...

Claims

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Application Information

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IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 纪顺俊刘欢汪顺义方毅
Owner SUZHOU UNIV
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