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Method for normal-pressure efficient synthesis of 6H-isoindole [2,1-a] indole-6-ketone compounds

A ketone compound, isoindole technology, applied in the field of organic synthesis, can solve the problems of harsh reaction conditions, complicated operation, low reagent or yield, etc., and achieve the effects of mild reaction conditions, simple operation, and wide application range of substrates

Active Publication Date: 2016-11-16
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have disadvantages such as cumbersome synthetic routes, complex operations, harsh reaction conditions, use of highly toxic reagents, or low yields, which largely limit the scope of application of this type of synthetic method.

Method used

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  • Method for normal-pressure efficient synthesis of 6H-isoindole [2,1-a] indole-6-ketone compounds
  • Method for normal-pressure efficient synthesis of 6H-isoindole [2,1-a] indole-6-ketone compounds
  • Method for normal-pressure efficient synthesis of 6H-isoindole [2,1-a] indole-6-ketone compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012]

[0013] Add indole 1a (0.4mmol, 109mg), palladium acetate (4.5mg, 0.02mmol), n-butylbis(1-adamantyl)phosphine (BDAP) ​​(21.5mg, 0.06mmol) into a 15mL schlenk reaction tube successively ), DABCO (134.6mg, 1.2mmol) and dimethyl sulfoxide (1.5mL), vacuum-filled with CO (1 atm) three times, then heated and stirred at 120°C for 12h. After the reaction was completed, a saturated ammonium chloride solution was added to the reaction tube to quench the reaction, extracted with dichloromethane, the organic phase was washed with deionized water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Filtered, spin-dried, and separated by silica gel column (petroleum ether / dichloromethane=3 / 1) to obtain 6H-isoindole[2,1-a]indol-6-one 2a (85mg, 97%) as a yellow solid . The characterization data of this compound are as follows: 1 H NMR (CDCl 3 ,400MHz)δ6.52(s,1H),7.12(t,J=7.6Hz,1H),7.24-7.30(m,2H),7.39-7.44(m,3H),7.70(d,J=7.6Hz ,1H),7.85(d,J=8.0Hz,1H)...

Embodiment 2

[0015] According to the method described in Example 1, indole 1a (0.4mmol, 109mg), PdCl 2 (3.5mg, 0.02mmol), n-butylbis(1-adamantyl)phosphine (BDAP) ​​(21.5mg, 0.06mmol), DABCO (134.6mg, 1.2mmol) and dimethylsulfoxide (1.5mL), Evacuated and filled with CO (1 atm) three times, then heated and stirred at 120°C for 12 hours to obtain the product 6H-isoindole[2,1-a]indol-6-one 2a (18 mg, 20%).

Embodiment 3

[0017] According to the method described in Example 1, indole 1a (0.4mmol, 109mg), Pd(PPh 3 ) 2 Cl 2 (14mg, 0.02mmol), n-butyl bis (1-adamantyl) phosphine (BDAP) ​​(21.5mg, 0.06mmol), DABCO (134.6mg, 1.2mmol) and dimethyl sulfoxide (1.5mL), extraction Vacuum filled with CO (1 atm) three times, then heated and stirred at 120°C for 12 hours to obtain the product 6H-isoindole[2,1-a]indol-6-one 2a (40mg, 46%). Example 4

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Abstract

The invention discloses a method for normal-pressure efficient synthesis of 6H-isoindole [2,1-a] indole-6-ketone compounds. The technical scheme of the invention has the key points that by taking 2-(2-bromoaryl)-1H-indole compounds and CO as starting materials, under the effects of transition metal palladium catalysts, ligands and alkali, heating and stirring reaction is carried out at 100-140 DEG C in an organic solvent so as to obtain target products, namely the 6H-isoindole [2,1-a] indole-6-ketone compounds. The method disclosed by the invention has the advantages that reaction conditions are mild, the starting materials are simple and easy to prepare, substrates are wide in range of application, and the operation is simple.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for efficiently synthesizing 6H-isoindole[2,1-a]indole-6-one compounds under normal pressure. Background technique [0002] Isoindoloindolones widely exist in natural alkaloids and biologically active molecules, and have attracted more and more attention and research from organic chemists and pharmacologists in recent years. Among them, 6H-isoindol[2,1-a]indol-6-ones not only have potential antitumor activity, but also have been successfully used as ligands of melatonin MT3 and Hnk1. Most of the 6H-isoindol[2,1-a]indol-6-one compounds in the literature are catalyzed by palladium. Palladium-catalyzed isonitrile or high-pressure CO (20atm) and 2-(2-bromoaryl)-1H-indole insertion reaction in the system. These methods have disadvantages such as cumbersome synthetic routes, complex operations, harsh reaction conditions, use of highly toxic reagents, or...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 郭胜海翟剑辉陶丽范学森
Owner HENAN NORMAL UNIV
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