Method for efficiently synthesizing indole and isoquinoline derivatives

A technology for isoquinoline and indole, which is applied in the field of efficient synthesis of indole and isoquinoline derivatives, can solve the problems of high temperature, low atom economy, and restriction on expansion of reaction substrates, and achieves clean reaction process and reduced Synthesis cost, high yield effect

Inactive Publication Date: 2016-01-06
LANZHOU 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

For example: Method 1, although some reaction conditions are mild, but expensive substrates and precious metal catalysts are required, and the expansion of reaction substrates is severely limited; Method 2, although some reactions can be carried out at room temperature, this type of reaction is an equivalent reaction , the reaction needs to be carried out step by step, and only one alkyne can be used as a reactant; method three, although some methods have been improved a lot, but this type of reaction requires an equivalent amount of expensive metal Cu, Ag or organic peroxide as an oxidant, and requires Higher temperature and less atom economy

Method used

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  • Method for efficiently synthesizing indole and isoquinoline derivatives
  • Method for efficiently synthesizing indole and isoquinoline derivatives
  • Method for efficiently synthesizing indole and isoquinoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1, the preparation of indole derivative 3aa

[0041] Its synthetic route is as follows:

[0042]

[0043] Aniline 1a (55.0μL, 0.6mmol), 1,2-toluene 2a (71.3mg, 0.4mmol), Cp*Rh(H 2 O) 3 (OTf) 2 (11.8mg, 5mol%), acetic anhydride (59.0μL, 0.6mmol), added to 2.0mL pivalyl alcohol, under oxygen (1atm), 40 o After 24 hours of reaction in C, the reaction was stopped. After adding NaOH (48mg, 1.2mmol) and methanol 2mL and stirring for one hour, the pure product 2,3-diphenylindole 3aa was obtained by column chromatography. The product was a white solid with a yield of 70%.

[0044] 1 3 δ7.13-7.17(m,1H),7.21-7.45(m,12H),7.67(d, J =7.68,1H),8.18(br,1H);

[0045] 13 CNMR (100MHz, CDCl 3 )δ110.9, 115.0, 119.7, 120.4, 122.7, 126.2, 127.7, 128.1, 128.5, 128.7, 128.7, 130.1, 132.7, 134.0, 135.0, 135.9;

[0046] HRMS(EI)calcd.forC 20 h 15 N[M]:269.1204,found:269.1205.

Embodiment 2

[0047] Embodiment 2, the preparation of indole derivative 3aa

[0048] Aniline 1a (55.0μL, 0.6mmol), 1,2-toluene 2a (71.3mg, 0.4mmol), Cp*Rh(H 2 O) 3 (OTf) 2 (11.8mg, 5mol%), acetic anhydride (59.0μL, 0.6mmol), added to 2.0mL tert-butanol, under oxygen (1atm), 40 o After 24 hours of reaction in C, the reaction was stopped. After adding NaOH (48mg, 1.2mmol) and methanol 2mL and stirring for one hour, the pure product 2,3-diphenylindole 3aa was obtained by column chromatography. The product was a white solid in 18% yield. Data characterization is the same as in Example 1.

Embodiment 3

[0049] Embodiment 3, the preparation of indole derivative 3aa

[0050] Aniline 1a (55.0μL, 0.6mmol), 1,2-toluene 2a (71.3mg, 0.4mmol), Cp*Rh(H 2 O) 3 (OTf) 2 (11.8mg, 5mol%), acetic anhydride (59.0μL, 0.6mmol), added to 2.0mL acetone, under oxygen (1atm), 40 o After 24 hours of reaction in C, the reaction was stopped. After adding NaOH (48mg, 1.2mmol) and methanol 2mL and stirring for one hour, the pure product 2,3-diphenylindole 3aa was obtained by column chromatography. The product was a white solid with a yield of 49%. Data characterization is the same as in Example 1.

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Abstract

The invention discloses a preparation method for substituted indole and isoquinoline, and belongs to the technical field of organic chemical synthesis. By adopting oxygen as an oxidizing agent and various substituent substituted alkyne and arylamine or hydrazone as an initial raw material, the method obtains compounds containing indole and isoquinoline structures by virtue of transition metal catalysis. The reaction raw materials, the oxidizing agent and the catalyst are low in price and are easily available, and the synthetic process is simple, so that the synthetic cost is greatly lowered; the reaction condition is mild, the yield is high, and industrialization is facilitated; The reaction raw materials and the catalyst are clean and non-toxic, so that the environmental pollution is less. The compounds and derivatives as important fine chemicals are widely applied to the fields of medicines, pesticides, spices, photoelectricity and the like.

Description

technical field [0001] The present invention relates to a kind of compound of indole and isoquinoline structure and the preparation method of substituted indole and isoquinoline, specifically, the preparation method adopts arylamine or arylhydrazone and alkyne substituted by various substituents As the starting material, through transition metal catalysis, compounds containing indole and isoquinoline structures can be obtained, and various substituted indole and isoquinoline compounds can be obtained by simple conversion of such compounds. Background technique [0002] Indole, isoquinoline and their derivatives, as an important fine chemical, have a wide range of uses in pesticides, medicines, spices and other industries. [0003] Indole nitrogen-containing heterocyclic ring is a common pharmacophore, which widely exists in various natural products and synthetic drugs with physiological activity, and is also a fragment of various functional materials. Substituted indoles ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C07D209/60C07D209/12C07D209/10C07D217/02C07D221/06C07D217/16C07D217/14
Inventor 黄汉民张国营
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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