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Synthesis method of 3-arylsulfonyl indole derivative

An arylsulfonyl indole derivative and a synthesis method technology are applied in the field of chemical organic synthesis, can solve the problems of poor reaction regioselectivity, high price, environmental pollution and the like, achieve high yield of target products, easy operation, Wide range of substrate effects

Inactive Publication Date: 2020-06-12
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

The above reactions need to use noble metals as catalysts, which are expensive and the metal residues will cause certain pollution to the environment, and the reaction regioselectivity is not good, and products replaced by other positions will be obtained.

Method used

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  • Synthesis method of 3-arylsulfonyl indole derivative
  • Synthesis method of 3-arylsulfonyl indole derivative
  • Synthesis method of 3-arylsulfonyl indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] In a sealed 25mL tube, add 1,5-enyne compound 2a (74mg, 0.2mmol), aryldiazonium salt 3a (124mg, 0.6mmol) and DABCO (SO 2 ) 2 (144mg, 0.6mmol), add 3mL solvent 1,2-dichloroethane under argon atmosphere, and react at 25°C for 12h. After the reaction, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C / ethyl acetate, v / v=10:1) to obtain the light yellow solid target Product 1a (100mg, yield 78%). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0030] Typical Compound Characterization Data

[0031] 3-Arylsulfonylindole derivative (1a), light yellow solid, melting point 100-102℃. 1 H NMR (400MHz, CDCl 3 ,23℃)δ8.43,7.72,7.60,7.55,7.47,7.40,and 7.31(m each,1:1:2:1:2:4:2H,aromatic CH),7.25(s,1H,aromatic CH ), 7.16, 7.09, and 6.99 (d each, J=8.0, 8.4, and 8.2Hz, 4:2:2H, aromatic CH), 2.38, 2.32, and 1.98 (seach, 3:3:3H, 3×CH 3 )....

Embodiment 2

[0033] The reaction steps and operations are the same as in Example 1, except that the reaction solvent is dichloromethane. The reaction was stopped, and the target product 1a (96 mg, yield 75%) was obtained after post-treatment.

Embodiment 3

[0035] The reaction steps and operations are the same as in Example 1, except that the reaction solvent is toluene. The reaction was stopped, and the target product 1a (58 mg, yield 45%) was obtained after post-treatment.

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Abstract

The invention discloses a synthesis method of a 3-arylsulfonyl indole derivative. A 1,5-eneyne compound which is easy to prepare and has structural diversity is used as a raw material to react with aryl diazonium salt and DABCO.(SO2)2 in a solvent to obtain the 3-arylsulfonyl substituted indole derivative. The method is simple and convenient to operate, wide in substrate range and mild in synthesis reaction condition, and functional groups of the method are diversified.

Description

technical field [0001] The invention belongs to the technical field of chemical organic synthesis, and relates to a synthesis method of 3-arylsulfonylindole derivatives. Background technique [0002] Indole is an important nitrogen-containing heterocycle that exists in a large number of natural products, among which arylsulfonyl substituted indole compounds are important indole derivatives, and 3-arylsulfonyl indole compounds have special Biologically active, it can be used as a tubulin inhibitor, platelet growth factor inhibitor, histone deacetylase inhibitor, etc., and has a good inhibitory effect on a variety of tumor cells. Therefore, the research on the synthesis method of 3-arylsulfonylindole compounds has important scientific significance. There are currently reports in the literature that InBr 3 Catalyzed reaction of indole with arylsulfonyl chloride to obtain 3-arylsulfonyl indole compound (Tetrahedron Letters 2003,44,6055-6058.); or o-alkynyl-N-sulfonyl catalyzed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30C07D403/04
CPCC07D209/30C07D403/04
Inventor 余正坤吴苹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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