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Fused bisindole derivatives and preparation method thereof

A technology for fused bisindole derivatives and indole, which is applied in the field of preparation of organic compounds, can solve the problems of harsh reaction conditions, high risk, and large pollution, and achieve easy availability of raw materials, various types, reduced pollution and production cost effect

Active Publication Date: 2020-02-11
翁后科
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation technology of existing indole derivatives has harsh reaction conditions (need to use acetylene gas as a reagent, expensive rhodium as a catalyst), low yield, high risk, and large pollution (heavy metal oxidant potassium permanganate and reducing agent chlorination Tin) and other defects

Method used

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  • Fused bisindole derivatives and preparation method thereof
  • Fused bisindole derivatives and preparation method thereof
  • Fused bisindole derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: 5-methyl-5,10-dihydroindoline[3,2- b ] Synthesis of indole

[0034] With 1-methyl-2-phenylindole as raw material, the reaction steps are as follows:

[0035] Add 1-methyl-2-phenylindole (0.21 g, 1 mmol), sodium nitrite (0.14 g, 2 mmol), potassium peroxodisulfate (0.54 g, 2 mmol) and acetone (5 mL ), nitrosation reaction was carried out at 60°C; TLC followed the reaction until it was completely completed; sampling was carried out for NMR, the yield was 95%, and the analysis data was as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.30 (dd, J = 5.7, 2.5 Hz, 1H), 7.91 – 7.79 (m, 2H), 7.66 – 7.56 (m, 3H), 7.49 –7.34 (m, 3H), 3.87 (s, 3H);

[0036] After the nitroso reaction, acetone was removed by rotary evaporation, and then triethylphosphite (0.83 g, 5 mmol) was added to the bottle, and the ring-forming reaction was carried out at 110 °C;

[0037] TLC followed the reaction until it was completely finished; the crude product obtained after the reaction w...

Embodiment 2

[0038] Example 2: Synthesis of 3-chloro-10-methyl-5,10-dihydroindo[3,2-b]indole

[0039]

[0040] Add 1-methyl-2-phenyl-5-chloroindole (0.24 g, 1 mmol), sodium nitrite (0.21 g, 3 mmol), potassium peroxodisulfate (0.54 g, 2 mmol) to a reaction vial and acetonitrile (5 milliliters), nitrosation reaction was carried out at 70°C; TLC tracked the reaction until it was completely completed; sampling was carried out for NMR, the yield was 96%, and the analysis data was as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.22 (d, J = 1.7 Hz, 1H), 7.85 – 7.74 (m, 2H), 7.64 – 7.53 (m, 3H), 7.34 –7.23 (m, 2H), 3.83 (s, 3H);

[0041] After the nitrosation reaction, acetonitrile was removed by rotary evaporation, then triethylphosphite (0.83 g, 5 mmol) was added to the bottle, and the ring-forming reaction was carried out at 110 °C;

[0042] TLC followed the reaction until it was completely completed; the crude product obtained after the reaction was separated by column chromatography ...

Embodiment 3

[0043] Example 3: Synthesis of 3-nitro-10-methyl-5,10-dihydroindo[3,2-b]indole

[0044] Add 1-methyl-2-phenyl-5-nitroindole (0.25 g, 1 mmol), sodium nitrite (0.21 g, 3 mmol), potassium peroxodisulfate (0.27 g, 1 mmol) to the reaction flask ) and dimethyl sulfoxide (5 ml), nitrosation reaction was carried out at 100°C; TLC followed the reaction until it was completely completed; sampling was carried out for NMR, the yield was 92%, and the analysis data was as follows: 1 H NMR (400 MHz, DMSO- d 6 ): δ 8.77 (m, 1H), 8.31 (m, 1H), 8.00 (m, 3H), 7.79 – 7.66 (m, 3H),3.95 (s, 3H).

[0045] After the nitrosation reaction, dimethyl sulfoxide was removed by rotary evaporation, then triethyl phosphite (0.83 g, 5 mmol) was added to the bottle, and the ring formation reaction was carried out at 120 °C;

[0046] TLC followed the reaction until it was completely over; the crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl aceta...

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Abstract

The invention discloses a fused bisindole derivative and a preparation method thereof. The preparation method provided by the invention comprises the following steps: adding an indole compound, sodiumnitrite and potassium persulfate into a solvent for reaction; and then, adding triethyl phosphite to obtain a product fused bisindole derivative. In the invention, the indole compound is used as a starting material; the raw materials are easily available and diversified; the obtained target product can be used directly and can also be used for other further reactions; sodium nitrite is used as anitrosating agent in the invention, is safe to use and cheap, reduces pollution and production costs, and meets requirements of green production; the preparation method disclosed in the invention is mild in reaction condition, simple in reaction operation and post-treatment process, stable and controllable in reaction process, high in product yield, and suitable for mass production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to the preparation of fused bisindole derivatives based on sodium nitrite. Background technique [0002] Indole derivatives are a class of natural products with a wide range of physiological activities, and have extensive and important applications in the fields of medicine and functional materials. (Reference 1: A. J. Kochanowska-Karamyan, M. T. Hamann, MarineIndole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety, Chem. Rev. 2010, 110, 4489–4497. Reference 2: S. Lancianesi, A. Palmieri , M. Petrini, Synthetic approaches to 3-(2-nitroalkyl) indoles and their use to access tryptamines and related bioactive compounds, Chem. Rev.2014, 114, 14, 7108-7149); In a variety of organic reactions, such as nitration reaction, cyclization reaction and nitroso-aldol reaction, etc.; fused bisindole compound I and its derivatives c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 邹建平陶泽坤达莫拉·苏布李成坤
Owner 翁后科
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