Azafluorenone derivative and preparation method and application thereof

A technology for azafluorenone and derivatives, applied in the field of azafluorenone derivatives and their preparation, can solve the problems of harsh reaction conditions, undeveloped, complicated steps and the like, and achieves the effect of increasing complexity

Active Publication Date: 2019-10-11
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although azafluorenones have achieved significant progress in the use of classical synthetic methods, there are still problems such as harsh reaction conditions, corresponding relatively complex precursors that must be synthesized in advance, and cumbersome steps.
In summary, the strategy of using simple and easy-to-obtain raw materials

Method used

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  • Azafluorenone derivative and preparation method and application thereof
  • Azafluorenone derivative and preparation method and application thereof
  • Azafluorenone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] This embodiment provides compound 1a, its preparation method is as follows:

[0071]5H-indeno[1,2-b]pyridin-5-one (1a), the reaction formula is as follows:

[0072]

[0073] Under air atmosphere, the aryl imide ester compound 2a (30.0mg, 0.2mmol) shown in formula (II) was sequentially added into the reactor, and the R of formula (II) 1 is hydrogen, a solution of olefin compound 3a (28.0mg, 0.4mmol) shown in formula (III) in 1,2-dichloroethane (0.5mL), R in formula (III) is Me, R' is hydrogen, Subsequently, 2.5 mg of dichloro(pentamethylcyclopentadienyl) rhodium dimer, 7.8 mg of bistrifluoromethanesulfonimide silver salt, 4.9 mg of sodium acetate and 12.0 mg of copper acetate were added successively. React for 30 minutes, then use a syringe to inject a solution of acetic acid (1.5mL) in terminal alkene 4a (40μL, 0.40mmol) into the reactor, R of formula (IV) 2 For hydrogen, the reaction temperature was raised to 120°C to continue the reaction for 24 hours. The end of...

Embodiment 2

[0077] This embodiment provides compound 1b, its preparation method is as follows:

[0078] The full name of 1b is 2-methyl-5H-indeno[1,2-b]pyridin-5-one (1b), and its reaction formula is as follows:

[0079]

[0080] Under air atmosphere, the aryl imide ester compound 2a (30.0mg, 0.2mmol) shown in formula (II) was sequentially added into the reactor, and the R of formula (II) 1 is hydrogen, a solution of olefin compound 3a (35.0mg, 0.5mmol) shown in formula (III) in 1,2-dichloroethane (0.5mL), R in formula (III) is Me, R' is hydrogen, Subsequently, 2.5 mg of dichloro(pentamethylcyclopentadienyl) rhodium dimer, 7.8 mg of bistrifluoromethanesulfonimide silver salt, 4.9 mg of sodium acetate and 12.0 mg of copper acetate were added successively. React for 30 minutes, then use a syringe to inject a solution of acetic acid (1.5mL) in terminal alkene 4b (40μL, 0.40mmol) into the reactor, R of formula (IV) 2 For Me, the reaction temperature was raised to 120°C to continue the re...

Embodiment 3

[0084] This embodiment provides compound 1c, its preparation method is as follows:

[0085] The full name of 1c is 7-iodo-5H-indeno[1,2-b]pyridin-5-one (1c), and its reaction formula is as follows:

[0086]

[0087] Under the air atmosphere, the aryl imide ester compound 2b (55.0mg, 0.2mmol) shown in formula (II) was sequentially added into the reactor, and the R of formula (II) 1 Halogen I, a solution of olefin compound 3a (28.0mg, 0.4mmol) represented by formula (III) in 1,2-dichloroethane (0.5mL), R in formula (III) is Me, R' is hydrogen , followed by adding 2.5 mg of dichloro(pentamethylcyclopentadienyl) rhodium dimer, 7.8 mg of bistrifluoromethanesulfonimide silver salt, 4.9 mg of sodium acetate and 12.0 mg of copper acetate, at 100 ° C The reaction was carried out for 30 minutes, and then a solution of acetic acid (1.5 mL) in terminal alkene 4a (40 μL, 0.40 mmol) was injected into the reactor with a syringe, and R of formula (IV) 2 For hydrogen, the reaction tempera...

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Abstract

The invention belongs to the technical field of organic synthesis and particularly relates to a polyfunctional-group-substituted azafluorenone derivative and a preparation method and application thereof. The structural formula of the azafluorenone derivative is shown as a formula (I), wherein Ar is an aryl group, the aryl group comprises an aromatic heterocyclic group, a phenyl group or aromatic fused ring group, R1 is selected from hydrogen, an ether group, halogen, acetyl, an ester group, trifluoromethyl or sulfuryl, and R2 is selected from hydrogen, alkyl, aryl, halogen, an ether group, trifluoromethyl, acetyl, an ester group or sulfuryl. By taking an aryl imido ester compound and olefin as substrates and under a metal catalysis effect, a cascade reaction of multiple times of aromatic ring carbon hydrogen bond activation based on aryl imine ester guidance and oxygen oxidation of alkyl carbon-carbon is achieved, and accordingly the poly-substituted azafluorenone derivative is rapidlyand modularly constructed. The azafluorenone medicine has a good application prospect in the development of organic photoelectric materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an azafluorenone derivative and a preparation method and application thereof. Background technique [0002] The field of modern organic synthesis not only pursues the synthesis of target compounds, but people have paid more attention to how to obtain target molecules in a simple, efficient and elegant manner. In this context, the use of more inert chemical bonds such as carbon-hydrogen bonds and carbon-carbon as substrates avoids cumbersome steps such as the synthesis, isolation, or pre-introduction of active functional groups of intermediate molecules, and becomes a new attractive synthetic method. Strategy. [0003] Although carbon-hydrogen bonds and carbon-carbon bonds have higher activation energies, and the number and types of carbon-hydrogen bonds that need to be considered when facing selective activation of such inert bonds (such as primary carbon-h...

Claims

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Application Information

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IPC IPC(8): C07D221/16C07D401/12
CPCC07D221/16C07D401/12
Inventor 饶建行李先纬欧阳文森
Owner GUANGDONG UNIV OF TECH
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