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A method for synthesizing indolo[3,2-b]carbazoles from o-alkenyl aryl isocyanides through cascaded cycloaddition reactions

A technology for aryl isocyanides and compounds, applied in the field of chemical organic synthesis, can solve problems such as no reports, single product structure, cumbersome steps, etc., and achieve the effects of simple raw materials, easy access to raw materials, and convenient experimental operations

Active Publication Date: 2021-01-22
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Summarizing the above-mentioned existing preparation methods, we find that there are the following problems: some methods or steps are relatively cumbersome; or the product structure is relatively simple
At the same time, the synthesis of indolo[3,2-b]carbazoles based on o-alkenyl aryl isocyanides via tandem cycloaddition reactions has not been reported yet.

Method used

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  • A method for synthesizing indolo[3,2-b]carbazoles from o-alkenyl aryl isocyanides through cascaded cycloaddition reactions
  • A method for synthesizing indolo[3,2-b]carbazoles from o-alkenyl aryl isocyanides through cascaded cycloaddition reactions
  • A method for synthesizing indolo[3,2-b]carbazoles from o-alkenyl aryl isocyanides through cascaded cycloaddition reactions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1 Synthesis of 6-methylformate-12-benzoyl-5,11-dihydroindo[3,2-b]carbazole (3aa)

[0040]

[0041] Add 3-(2-isocyanophenyl)methyl acrylate 1a (112.2mg, 0.6mmol), 3-(2-oxo-2-phenylethylidene)-indoline into a 10mL pressure-resistant tube -2-Kone 2a (74.7mg, 0.3mmol), zinc chloride (12.3mg, 0.09mmol), ethylene glycol dimethyl ether (GDME) 1mL, put it into 130 ℃ and stir, TLC monitoring 2a basically After disappearing, pour the reaction solution into 4mL saturated aqueous sodium chloride solution, add hydrochloric acid (1mol L -1 ) to remove the remaining 1a, extract 3 times with dichloromethane, combine the organic phases, and distill under reduced pressure. The crude product was separated by silica gel column chromatography (petroleum ether:ethyl acetate:dichloromethane=30:1:1) to obtain the product 3aa as a red solid (86.2 mg, 69%).

[0042] Spectrum analysis data 3aa

[0043] 1 H NMR nuclear magnetic resonance spectrum: (DMSO-d 6 ,400MHz)δ4.24(s,3H),6.96...

Embodiment 2

[0048] Example 2 Synthesis of 6-methylformate-12-(4-methylbenzoyl)-5,11-dihydroindo[3,2-b]carbazole (3ab)

[0049] Add 3-(2-isocyanophenyl)methyl acrylate 1a (112.2mg, 0.6mmol), 3-(2-oxo-2-(4-methylphenyl)ethylene base)-indoline-2-one 2b (86.6mg, 0.3mmol), zinc chloride (12.3mg, 0.09mmol), ethylene glycol dimethyl ether 1mL, put it into 130 ℃ and stir, TLC After monitoring that 2b disappeared substantially, the reaction solution was poured into 4mL saturated aqueous sodium chloride solution, and hydrochloric acid (1mol L -1 ) to remove the remaining 1a, extract 3 times with dichloromethane, combine the organic phases, and distill under reduced pressure. The crude product was separated by silica gel column chromatography (petroleum ether:ethyl acetate:dichloromethane=30:1:1) to obtain orange solid 3ab (95.9 mg, 74%).

[0050] Spectral Analysis Data 3ab

[0051] 1 H NMR nuclear magnetic resonance spectrum: (DMSO-d 6 ,400MHz)δ2.33(s,3H),4.23(s,3H),6.96(t,J=7.6Hz,1H),7.20(t,J...

Embodiment 3

[0054] Example 3 Synthesis of 6-methylformate-12-(3,4-dimethoxybenzoyl)-5,11-dihydroindo[3,2-b]carbazole (3ac)

[0055] Add 3-(2-isocyanophenyl)methyl acrylate 1a (112.2mg, 0.6mmol), 3-(2-(3,4-dimethoxyphenyl)-2- Oxyethylene) indoline-2-one 2c (92.7mg, 0.3mmol), zinc chloride (12.3mg, 0.09mmol), ethylene glycol dimethyl ether 3mL, put it under the condition of 130 ℃ Stir, after TLC monitors that 2c disappears substantially, the reaction solution is poured into 4mL saturated aqueous sodium chloride solution, and hydrochloric acid (1mol L -1 ) to remove the remaining 1a, extract 3 times with dichloromethane, combine the organic phases, and distill under reduced pressure. The crude product was separated by silica gel column chromatography (petroleum ether:ethyl acetate:dichloromethane=25:1:1) to obtain a yellow solid 3ac (87.5 mg, 61%).

[0056] Spectral analysis data 3ac

[0057] 1 H NMR nuclear magnetic resonance spectrum: (CDCl 3 ,400MHz)δ3.86(s,3H),3.86(s,3H),4.27(s,3H),...

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Abstract

The invention discloses a method for synthesizing indolo[3,2-b] carbazole compounds from o-allyl aryl isonitrile through a cascade cycloaddition reaction and belongs to the technical field of chemicalorganic synthesis. The method specifically comprises the following steps: mixing alkylene indolone compounds and o-allyl aryl isonitrile compounds according to a molar ratio ranging from 1:1 to 1:3,respectively adding a catalyst and a solvent, carrying out a reaction at a temperature of 100-150 DEG C for 27-48 hours, and performing TLC monitoring until the alkylene indolone compounds disappear;pouring the reaction solution into an aqueous solution of saturated sodium chloride, adding diluted hydrochloric acid to remove the residual o-allyl aryl isonitrile compounds until the o-allyl aryl isonitrile compounds disappear by virtue of the TLC monitoring; extracting with dichloromethane, merging the organic phase, performing reduced pressure distillation to obtain a crude product, and performing silica-gel column chromatography separation on the crude product, thereby obtaining the final product. The indolo[3,2-b] carbazole compounds prepared according to the method have diversity, and can be regulated by virtue of different raw materials such as the o-allyl aryl isonitrile compounds or the alkylene indolone compounds.

Description

technical field [0001] The invention belongs to the technical field of chemical organic synthesis, and in particular relates to a method for synthesizing indolo[3,2-b]carbazole compounds from o-alkenyl aryl isonitriles through series cycloaddition reactions. Background technique [0002] Indolocarbazole includes five isomers, namely indolo[2,3-a]carbazole, indolo[2,3-b]carbazole, indolo[2,3- c] carbazole, indolo[3,2-a]carbazole, indolo[3,2-b]carbazole. Among the five isomers, indolo[3,2-b]carbazole is more researched and applied, and its molecular structure is shown below: [0003] [0004] Since indolo[3,2-b]carbazole has a condensed ring structure similar to pentacene, this type of compound generally has a larger band gap and a lower energy level of the highest occupied orbital. The yoke planar structure is helpful for carrier transport, and its rigid planar structure makes this kind of compound have good thermal stability. In addition, compared with pentacene, indol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 张大伟张雪明马正宁
Owner JILIN UNIV
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