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Synthetic method of carbazole and its derivatives

A synthetic method and derivative technology, applied in the direction of organic chemistry, etc., can solve the problems of not being able to meet the needs of diversity and single products, and achieve the effects of high product yield, simple synthetic route, and strong practicability

Active Publication Date: 2019-06-07
JIANGHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, with the increasing demand for research and production, the demand for carbazole and its derivatives has been increasing year by year. Although the compounds synthesized by traditional methods are relatively economical, the products are single and cannot meet the needs of diversity.

Method used

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  • Synthetic method of carbazole and its derivatives
  • Synthetic method of carbazole and its derivatives
  • Synthetic method of carbazole and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1 synthetic compound (1-1)

[0040]

[0041] Add H to the 250mL reaction flask 2 O (50mL), THF (50mL), 3-indole formaldehyde (5mmol, 726mg), 3-bromopropene (10mmol, 1290mg), 1,4-dihydropyridinate (5mmol, 1176mg) and indium powder (7mmol, 803mg). The reaction mixture was reacted at 50° C. for 24 hours, and the reaction was complete as detected by TLC. Post-processing purification: the reaction mixture was extracted with EA (20 mL×2), and the organic phases were combined and washed with saturated NaCl (20 mL×1). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 15:1] to obtain a pure product, light yellow Liquid, yield: 75%.

[0042] Compound (1-1) was detected:

[0043] 1 H NMR (400MHz, CDCl 3 ):δ7.93(s,1H),7.65(dd,J=7.9Hz,J=1.0Hz,1H),7.39(dt,J=8.1Hz,J=0.8Hz,1H)7.25-7.19(m, 1H), 7.17-7.12...

Embodiment 2

[0045] Embodiment 2 synthetic compound (1-2)

[0046]

[0047] Compound (1-1) (5 mmol, 856 mg), DMF (10 mL) and NaH (5 mmol, 240 mg) were added to a 25 mL two-necked flask. The reaction mixture was stirred at 0° C. for 10 minutes, and then 2-chloropyrimidine (6 mmol, 687 mg) was added, then raised to room temperature and reacted at 130° C., and the reaction was complete as detected by TLC. Post-treatment purification: add water (20 mL) to quench, extract with EA (20 mL×3), combine organic phases, and wash with saturated NaCl (20 mL×2). After liquid separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, and separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 8:1] to obtain a pure product, colorless Liquid, yield: 80%.

[0048] Compound (1-2) is tested:

[0049] 1 H NMR (400MHz, CDCl 3 )δ8.78(d, J=8.3Hz, 1H), 8.65(d, J=4.8Hz, 2H), 8.05(s, 1H), 7.58(d, J=7.8Hz, 1H), 7.37-7.31( m...

Embodiment 3

[0053] Embodiment 3 synthetic compound (1-3)

[0054]

[0055] In a 10 mL Schlenk tube, add compound (1-2) (0.2 mmol, 49.86 mg), silver acetate (0.3 mmol, 50.1 mg), potassium trifluorovinyl borate (0.3 mmol, 40.2 mg), [RhCp*Cl 2 ] 2 (1mol%, 1.24mg), methanol (1mL), TFE (1mL) and air balloon (1L). The reaction mixture was reacted at 40° C. and detected by TLC until the reaction was complete. Carry out post-processing purification: remove the organic solvent under reduced pressure, separate and purify with silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 8: 1] to obtain a pure product, a colorless liquid, and the yield: 85%.

[0056] Compound (1-3) was detected:

[0057] 1 H NMR (400MHz, CDCl 3 )δ8.77(d, J=4.8Hz, 2H), 8.25(d, J=8.4Hz, 1H), 7.63-7.56(m, 1H), 7.32-7.19(m, 2H), 7.12-7.07(m ,1H),6.99(dd,J=17.4,11.9Hz,1H),5.98(dt,J=16.9,10.2,6.6Hz,1H),5.43(s,1H),5.41-5.37(m,1H), 5.15-5.09(m,1H),5.05-4.99(m,1H),2.98(dd,J=8.4,7.6Hz,2H),2.47(dd,J=7.8...

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Abstract

The invention discloses a synthesis method of carbazole and its derivatives. The synthesis method undergoes N substitution reaction, vinylation reaction, removal of R 2 Group and olefin ring-closing metathesis reaction to obtain carbazole and its derivatives. The synthesis method of carbazole and its derivatives described in the present invention can synthesize various derivatives of carbazole according to the substituents on the indole ring of the raw material, and there is no substituent on the N of carbazole, which can be carried out as an intermediate as required Synthesis in the next step. Simultaneously, the present invention synthesizes carbazole and its derivatives by using abundant raw materials to meet the huge demand of carbazole and its derivatives. In addition, the synthesis route of the present invention is simple, the reaction conditions are easy to control and realize, the product yield is high, and it has strong practicability.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing carbazole and derivatives thereof. Background technique [0002] Carbazole, also known as dibenzopyrrole, naturally exists in coal tar and is an important organic synthesis intermediate and chemical raw material. Its traditional use is for the synthesis of dyes and pigments, for example: for the production of sulfur dyes Haichang blue, tetrabromo Haichang blue and permanent violet RL and so on. The latest research has found that various types of carbazole derivatives with novel structures can be obtained by chemically modifying carbazole by introducing various substituent groups or functional groups at specific positions of the carbazole molecule. At present, many of them have been used as drugs or drug intermediates. For example, 3-acetylaminocarbazole, bromocarbazole and 4-hydroxycarbazole have shown certain biological activities, so their application...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07D209/86C07D209/12C07D209/88C07D403/04
CPCC07D209/08C07D209/12C07D209/86C07D209/88C07D403/04
Inventor 王亮谢浩浩张玉敏
Owner JIANGHAN UNIVERSITY