Bis-triazole pentacene quinone compound and preparation method thereof
A compound, the technology of pentabenzoquinone, which is applied in the field of chemical synthesis, can solve the problems of poor solubility and achieve the effect of simplifying the preparation process
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Examples
Embodiment 1
[0027] 2,10-dioctyl-pentacene[2,3-d:9,10-d']bis([1,2,3]triazole)-6,14(2H,10H)-dione ( A4)
[0028]
[0029] The preparation method of above-mentioned formula (A4) compound is as follows
[0030] S101: Preparation of 5,6-dimethyl-2-octyl-2H-benzo[d][1,2,3]triazole (A1):
[0031]
[0032] 5,6-Dimethyl-2H-benzo[d][1,2,3]triazole (2.94 g, 20 mmol), sodium hydroxide (960 mg, 24 mmol) and catalytic amount of tetrabutylammonium bromide Dissolve in DMSO (250mL); remove the air in the reaction system, fill with argon; add 1-bromooctane (3.86g, 20mmol), and stir the reaction at room temperature; after reacting for 16 hours, add ethyl acetate to extract the mixture, It was washed with water again, and the organic phase was washed with saturated brine, then dried (anhydrous magnesium sulfate), and concentrated. The product was purified by column chromatography (petroleum ether / ethyl acetate, 15:1) to obtain product (A1) (2.07 g, 40%).
[0033] S102: Preparation of 5,6-bis(bromom...
Embodiment 2
[0043] 2,10-Dihexyl-pentacene[2,3-d:9,10-d']bis([1,2,3]triazole)-6,14(2H,10H)-dione (B4 )
[0044]
[0045] The preparation method of above-mentioned formula (B4) compound is as follows
[0046] S201: Preparation of 5,6-dimethyl-2-hexyl-2H-benzo[d][1,2,3]triazole (B1):
[0047]
[0048] 5,6-Dimethyl-2H-benzo[d][1,2,3]triazole (2.94 g, 20 mmol), sodium hydroxide (960 mg, 24 mmol) and catalytic amount of tetrabutylammonium bromide Dissolve in DMSO (250mL); remove the air in the reaction system, fill with argon; add 1-bromohexane (3.30g, 20mmol), and stir the reaction at room temperature; after reacting for 1 hour, add ethyl acetate to extract the mixture, It was washed with water again, and the organic phase was washed with saturated brine, then dried (anhydrous magnesium sulfate), and concentrated. The product was purified by column chromatography (petroleum ether / ethyl acetate, 15:1) to obtain product (B1) (1.94 g, 42%).
[0049] S202: Preparation of 5,6-bis(bromomet...
Embodiment 3
[0059] 2,10-Didecyl-pentacene[2,3-d:9,10-d']bis([1,2,3]triazole)-6,14(2H,10H)-dione ( C4)
[0060]
[0061] The preparation method of above-mentioned formula (C4) compound is as follows
[0062] S301: Preparation of 5,6-dimethyl-2-decyl-2H-benzo[d][1,2,3]triazole (C1):
[0063]
[0064] 5,6-Dimethyl-2H-benzo[d][1,2,3]triazole (2.94 g, 20 mmol), sodium hydroxide (960 mg, 24 mmol) and catalytic amount of tetrabutylammonium bromide Dissolve in DMSO (250mL); remove the air in the reaction system, fill with argon; add 1-bromodecane (4.42g, 20mmol), and stir the reaction at room temperature; after reacting for 16 hours, add ethyl acetate to extract the mixture, It was washed with water again, and the organic phase was washed with saturated brine, then dried (anhydrous magnesium sulfate), and concentrated. The product was purified by column chromatography (petroleum ether / ethyl acetate, 15:1) to obtain product (C1) (2.58 g, 45%).
[0065] S302: Preparation of 5,6-bis(bromom...
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Description
Claims
Application Information
- IPC
- C07D487/04
- CPC
- C07D487/04
- Inventors
- 师自法; 许年胜