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Method for preparing benzimidazole [2, 1-a] isoquinoline-6 (5H)-ketone compound

A technology of ketone compounds and benzimidazoles, which is applied in the field of organic synthesis to achieve a wide range of effects

Active Publication Date: 2022-03-01
HUAIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the methods for introducing cyanoalkyl / and ketone structures so far require the use of brominated raw materials as radical precursors, and the reaction needs to be carried out under the conditions of an expensive photocatalytic redox system (J.Org.Chem.2020, 85 , 11892-11901; RSC Adv., 2021, 11, 29372)

Method used

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  • Method for preparing benzimidazole [2, 1-a] isoquinoline-6 (5H)-ketone compound
  • Method for preparing benzimidazole [2, 1-a] isoquinoline-6 (5H)-ketone compound
  • Method for preparing benzimidazole [2, 1-a] isoquinoline-6 (5H)-ketone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0035]

[0036] Add N-methacryloyl-2-phenylbenzimidazole compound (52.4 mg, 0.2 mmol) shown in formula 1a, acetonitrile (1.0 mL) shown in formula 2a, scandium trifluoromethanesulfonate in the Schlenk bottle (19.7mg, 20mol%), tert-butyl peroxybenzoate (77.7mg, 0.4mmol), then the reactor is stirred and reacted under 130 ℃, air atmosphere, disappears to raw material through TLC monitoring reaction progress (the reaction time is 10 hours), after the reaction was completed, the reaction solution was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain target product I-1 (33%yield); 1 H NMR (500MHz, CDCl 3 )δ: 8.52-8.50 (m, 1H), 8.34-8.32 (m, 1H), 7.84-7.80 (m, 1H), 7.66-7.62 (m, 1H), 7.56-7.53 (m, 1H), 7.49- 7.47(m, 1H), 7.46-7.42(m, 2H), 2.92-2.86(m, 1H), 2.43-2.3...

Embodiment 2

[0038] The catalyst is silver carbonate instead of scandium trifluoromethanesulfonate, and the remaining conditions are the same as in Example 1, and the yield of the target product I-1 is 42%.

Embodiment 3

[0040] Catalyst replaced scandium trifluoromethanesulfonate with copper chloride, other conditions were the same as in Example 1, and the yield of the target product I-1 was 31%.

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Abstract

The invention relates to a method for preparing a benzimidazole [2, 1-a] isoquinoline-6 (5H)-ketone compound. The method comprises the following steps: adding an N-methylacryloyl-2-phenyl benzimidazole compound, a nitrile compound / acetone / tert-butyl nitrite, a catalyst, an oxidizing agent and a solvent into a Schlenk reaction flask, and stirring and reacting at a certain temperature in an air atmosphere to obtain the cyanogen-containing alkyl / ketone skeleton / nitro-substituted benzimidazole [2, 1-a] isoquinoline-6 (5H)-ketone compound.

Description

technical field [0001] The application belongs to the field of organic synthesis, and specifically relates to a new method for preparing benzimidazol[2,1-a]isoquinolin-6(5H)-one compounds containing cyanoalkyl / ketone skeleton / nitro substitution. Background technique [0002] As an efficient synthon, 2-arylbenzimidazoles participate in many transformations to construct C-C, C-N and C-S bonds. Among them, the most important class of reactions is radical cyclization, a strategy that enables the transformation of simple starting materials into more complex polycyclic molecules under mild conditions. In recent years, many examples of preparing various benzimidazol[2,1-a]isoquinolin-6(5H)-ones through radical cyclization reactions of 2-arylbenzimidazoles have been reported. Meanwhile, as a ubiquitous drug structural motif, the medicinal value of benzimidazol[2,1-a]isoquinolin-6(5H)-one shows wide applications in modern medicine, such as in Anti-diabetes, anti-tumor diseases, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 刘益林唐伯孝连琰彭官敏魏文廷林红卫舒月
Owner HUAIHUA UNIV
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