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Sulfonylated indolo[1,2-a]quinoline compounds and preparation method thereof

A technology for sulfonylated indole and arylalkynyl phenyl indole compounds, which is applied in the field of preparation of sulfonylated indolo[1,2-a]quinoline compounds, and achieves high yield and regioselectivity High and easily available raw materials

Active Publication Date: 2021-05-04
ZHENGZHOU UNIV
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AI Technical Summary

Problems solved by technology

[0003] At present, the synthesis method of sulfonylated indolo[1,2-a]quinolines has not been reported. Therefore, it is urgent to find a fast and efficient, simple steps, mild reaction conditions and high regioselectivity. Synthetic method of indolo[1,2-a]quinoline compounds

Method used

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  • Sulfonylated indolo[1,2-a]quinoline compounds and preparation method thereof
  • Sulfonylated indolo[1,2-a]quinoline compounds and preparation method thereof
  • Sulfonylated indolo[1,2-a]quinoline compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation method of sulfonylated indolo [1,2-a] quinoline, the steps are as follows:

[0023] In a 25 mL reaction tube, add o-aryl alkynyl phenylindole (0.5 mol), p-toluenesulfonyl hydrazide (1 mmol), solvent methanol 5 mL, tetrabutylammonium iodide (0.05 mmol), tert-butyl peroxide Hydrogen oxide was 2 mmol, stirred and refluxed at 60 °C for 12 h, and the final product was separated by silica gel column chromatography. The yield of the final product was 85% based on the o-arylkynylphenylindole molar weight as 100%.

[0024] The specific results are as follows:

[0025]

[0026] 1 H NMR (400 MHz, CDCl 3 ) δ 8.76 (dd, J = 8.3, 1.4 Hz, 1H), 8.46 (d, J =8.0, 1H), 8.37 (d, J = 8.6 Hz, 1H), 7.75 (d, J = 8.0, 1H), 7.61-7.54 (m, 2H),7.54-7.34 (m, 6H), 7.34-7.20 (m, 3H), 7.12 (d, J = 8.0 Hz, 2H), 2.33 (s, 3H),1.56 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 143.3, 140.3, 140.1, 136.0, 135.7,132.4, 131.6, 130.3, 130.0, 129.4, 129.0, 128.3, 128.1, 127.8, 127.7, 1...

Embodiment 2

[0028] The preparation method of sulfonylated indolo [1,2-a] quinoline, the steps are as follows:

[0029] In a 25 mL reaction tube, add o-aryl alkynylphenylindole (0.5 mol), benzenesulfonyl hydrazide (1 mmol), solvent methanol 5 mL, tetrabutylammonium iodide (0.05 mmol), tert-butyl peroxide Hydrogen 2 mmol, stirred and refluxed at 60 °C for 12 h, and the final product was obtained by silica gel column chromatography. The yield of the final product was 83 % based on the molar weight of o-aryl alkynyl phenyl indole as 100 %.

[0030] The specific results are as follows:

[0031]

[0032] 1 H NMR (400 MHz, CDCl 3 ) δ 8.76 (dd, J = 8.4, 1.4 Hz, 1H), 8.47 (d, J =8.4 Hz, 1H), 8.38 (d, J = 8.4 Hz, 1H), 7.75 (d, J = 8.0 Hz, 1H), 7.67-7.65(m, 2H), 7.56-7.50 (m, 2H), 7.45-7.34 (m, 5H), 7.32 (t, J = 7.6 Hz, 2H),7.29-7.24 (m, 3H), 1.57 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 143.37, 140.42,136.06, 135.56, 132.52, 132.47, 131.62, 130.29, 130.18, 129.10, 128.82,128.41, 127....

Embodiment 3

[0034] The preparation method of sulfonylated indolo [1,2-a] quinoline, the steps are as follows:

[0035] Add o-aryl alkynylphenylindole (0.5 mol), bromobenzenesulfonyl hydrazide (1 mmol), solvent methanol 5 mL, tetrabutylammonium iodide (0.05 mmol), tert-butyl Hydrogen peroxide (2 mmol), stirred and refluxed at 60 °C for 12 h, separated by silica gel column chromatography to obtain the final product, the yield of the final product was 65 % based on the molar weight of o-aryl alkynylphenylindole as 100 % .

[0036] The specific results are as follows:

[0037]

[0038] 1 H NMR (400 MHz, CDCl 3 ) δ 8.75 (dd, J = 8.4, 1.4 Hz, 1H), 8.49 (dd, J = 8.5, 1.1 Hz, 1H), 8.39 (d, J = 8.6 Hz, 1H), 7.77 (dt, J = 8.2, 1.0 Hz, 1H),7.58 (ddd,J = 8.6, 7.3, 1.5 Hz, 1H), 7.55-7.46 (m, 3H), 7.46-7.39 (m, 4H),7.39-7.31 (m, 1H), 7.31-7.21 (m, 3H), 1.57 (s , 3H). 13 C NMR (101 MHz, CDCl 3 ) δ142.38, 140.38, 136.04, 135.34, 132.51, 132.00, 131.63, 130.29, 130.19,129.24, 128.59, 128....

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Abstract

The invention discloses a sulfonylated indolo[1,2-a]quinoline compound and a preparation method thereof. The invention uses o-aryl alkynyl phenyl indole and aryl sulfonyl hydrazide as raw materials, Synthesis of sulfonylated indolo[1,2‑a]quinoline compounds under the action of ammonium iodide and tert-butyl hydroperoxide. The raw materials are cheap and easy to obtain, the reaction conditions are mild, the operation is simple, and the synthesis yield is high, which is beneficial to industrial production. Such derivatives have potential applications in the fields of chemical industry, medicine, etc., and the present invention provides a method for the synthesis of sulfonylated indolo[1,2-a]quinoline compounds for the first time.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of sulfonylated indolo[1,2-a]quinoline compounds. Background technique [0002] Indolo[1,2-a]quinoline compounds are an important class of polyheterocyclic compounds with unique physical, chemical and biological activities, and have extremely important applications in the fields of organic synthetic chemistry, materials chemistry and medicinal chemistry. The research on the synthesis method and properties of indolo[1,2-a]quinoline and its derivatives is still a research hotspot of common concern for chemistry, pharmacy, physics and materials scientists ( J. Org. Chem. 2011, 76 (14), 5670). In addition, sulfone compounds are important intermediate structures in organic synthesis, and exhibit a wide range of physical, chemical and biological activities in the fields of agriculture and medicinal chemistry ( Chem. Commun. 2015, 51 , 12111, Tetrahedron Le...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 陈晓岚孙凯於兵屈凌波
Owner ZHENGZHOU UNIV
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