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Method for one-step synthesis of 2-aminoindolo [2, 3-b] indole derivative

A technology of indole derivatives and aminoindole, applied in the direction of organic chemistry, can solve the problems of limited substituent groups, pre-preparation of substrates, harsh reaction conditions, etc. simple effect

Pending Publication Date: 2020-06-12
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, there are still many obvious shortcomings in the above method, such as: the substrate is too special and needs to be pre-prepared, the use of noble metal catalysts, harsh reaction conditions and the limitation of substituent groups are large, etc.

Method used

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  • Method for one-step synthesis of 2-aminoindolo [2, 3-b] indole derivative
  • Method for one-step synthesis of 2-aminoindolo [2, 3-b] indole derivative
  • Method for one-step synthesis of 2-aminoindolo [2, 3-b] indole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 0.5 mmol diphenylamine, 0.375 mmol N-methylindole, 0.075 mmol copper chloride, 10 mg to a Schlenk tube Molecular sieves, 0.25mL 1,4-dioxane, at 80°C, O 2 After stirring and reacting for 16 hours under conditions (the oxygen pressure used is one atmospheric pressure), stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The volume ratio of the deliquified petroleum ether: ethyl acetate mixed solvent is 20:1.

[0036] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows figure 1 and figure 2 As shown, the structural characterization data are as follows:

[0037] 1 H NMR (400MHz, Chloroform-d) δ7.68 (d, J = 6.8Hz, 1H), 7.62 (s, 1H), 7.48–7.35 (m, 5H), 7.15 (d, J = 7.2Hz, 1H) ,7.12–6.97(m,11H),6.81(t,J=7.2Hz,3H),3.32(s,3H).

[0038] 13 C NMR(100MHz,Chloroform-d)δ148....

Embodiment 2

[0044] In a Schlenk tube add 0.5 mmol 4-bromodiphenylamine, 0.375 mmol N-methylindole, 0.075 mmol cuprous chloride, 0.05 mmol ammonium iodide, 0.05 mmol 4-dimethylaminopyridine, 1.5 mL 1,4 - Dioxane, at 60°C, O 2 After stirring and reacting for 16 hours under conditions (the oxygen pressure used is one atmospheric pressure), stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The volume ratio of the deliquified petroleum ether: ethyl acetate mixed solvent is 20:1.

[0045] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows image 3 and Figure 4 As shown, the structural characterization data are as follows:

[0046] 1 H NMR (400MHz, Chloroform-d) δ7.80(d, J=7.9Hz, 1H), 7.76–7.66(m, 3H), 7.43(d, J=8.3Hz, 2H), 7.29(d, J= 8.3Hz, 3H), 7.25–7.19(m, 4H), 7.14(d, J=7.8Hz, 2H), 7....

Embodiment 3

[0053] Add 0.25mmol diphenylamine, 0.25mmol 4,4'-dimethyldiphenylamine, 0.375mmol N-methylindole, 0.075mmol copper chloride, 10mg to a Schlenk tube Molecular sieves, 2.5mL 1,4-dioxane, at 100°C, O 2 After stirring and reacting for 16 hours under conditions (the oxygen pressure used is one atmospheric pressure), stop heating and stirring, cool to room temperature, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product. The volume ratio of the deliquified petroleum ether: ethyl acetate mixed solvent is 20:1.

[0054] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows Figure 5 and Figure 6 As shown, the structural characterization data are as follows:

[0055] 1 H NMR (500MHz, Chloroform-d) δ7.72–7.69(m,1H),7.63–7.59(m,1H),7.50–7.45(m,4H),7.43–7.39(m,1H),7.19(dd ,J=6.4,2.2Hz,1H),7.14–7.08(m,3H),7.07–7.01(m,1H),6.99(dd,J=8.6,1.9H...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a method for one-step synthesis of a 2-aminoindolo [2, 3-b] indole derivative. The method comprises the steps: adding an arylamine compound, an indole compound, a metal catalyst, a ligand, an additive, an oxidant and a solvent in a reactor, carrying out a stirring reaction at 60-100 DEG C for 1-24 h, cooling to room temperature after the reaction is finished, carrying out reduced pressure rotary evaporation to remove the solvent so as to obtain a crude product, and carrying out column chromatography purification on the crude product so as to obtain the 2-aminoindolo [2, 3-b] indole derivative, wherein the arylamine compound is an arylamine compound with a structure as shown in a formula (1), and the indole compound is an indole compound with a structure as shown in a formula (2). The method has the advantages of simple synthesis steps, safety in operation, non-toxic, cheap and easily available raw materials, good compatibility of the synthesis method to functional groups, high chemical selectivity, high atom economy and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing 2-aminoindolo[2,3-b]indole derivatives in one step. Background technique [0002] Indolo[2,3-b]indole is a multi-component fused-ring aromatic compound, and the structural unit has a large π-conjugated system and weak electron-donating ability. Alternative copolymerization of intramolecular weak donor-strong acceptor structural units is one of the effective means to obtain organic semiconductor materials with ideal energy level structure. At present, indoloindole compounds have been widely used in Organic Light-emitting Diodes (OLEDs), Organic Field-effect Transistors (OFETs), Organic Solar Cells (OSC) ) and organic photovoltaic cells (Organic Photovoltaic Cells (OPC)) and other functional materials. ((a) Lai, Y-Y.; Yeh, J-M.; Tsai, C-E.; Cheng, Y-J.Eur.J.Org.Chem.2013 , 2013, 5076–5084; (b) Wu, W.; Liu, Y.; Zhu, D. Chem Soc Rev. 2010, 39, 14...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D471/16
CPCC07D487/04C07D471/16
Inventor 张珉梁桃源
Owner SOUTH CHINA UNIV OF TECH